Wikipedia talk:WikiProject Chemicals/Archive 2011

Archive 2005

←

Archive 2009

Archive 2010

Archive 2011

Template:Chembox SystematicName proposed for deletion (TFD)

The Template:Chembox SystematicName has been proposed for deletion (TFD) by User:Plasmic Physics on January 2 2011. More discussion here on his invitation: Wikipedia:Templates_for_discussion/Log/2011_January_1#Template:Chembox_SystematicName. For information. Shinkolobwe (talk) 13:49, 2 January 2011 (UTC)

Quotation from text above:
If the entry Template:Chembox SystematicName is irrelevant, inappropriate, and unsourceable, then I propose that such a useless entry be deleted. --Plasmic Physics (talk) 21:15, 31 December 2010 (UTC)

Answer: A priori, I would trend to agree with this proposal, but only for simple inorganic substances. However, the question is more complex. As I already previously mentioned it, I personally consider that the Template:Chembox SystematicName is often of poor added value for simple inorganic compounds and can be easily misleading for inexperienced persons. Meanwhile, this point of view must be temperated because this template can be more useful and better adapted for more complex organic compounds. It is not because an entry exists that it is mandatory to use it. Everything is a simple question of judicious appreciation and common sense. I would leave the freedom to use it when it is meaningful (organic chemistry) and to omit it when appropriate (mineral chemistry).
Personally, I do not feel obliged to use an entry simply because it exists. I only try to follow the KISS principle: Keep It Simple and Straithforward (Stupid) to deliver a sound and clear information. Regards, Shinkolobwe (talk) 23:51, 1 January 2011 (UTC)

Before to delete this general template, the main advantages and disadvantages of such an option should be carefully assessed and all the possible outcomes well weighted. It could potentially solve the numerous discussions and the polemic arisen from the very specialized edits made by User:Plasmic Physics in the chemboxes of simple inorganic substances but it could also have a much more severe impact on these of some complex organic substances whose IUPAC names could be lost. I have no ideas on the number of chemboxes that could be negatively affected in case of suppression of this template in use since more than 3.5 years. It seems wize to reach a consensus on the question before administrators take a decision in that matter. Shinkolobwe (talk) 13:49, 2 January 2011 (UTC)

Dirk Beetstra created this template on 22 March 2007 and is presently away on holiday. As announced on his talk page he may not respond swiftly to queries. It would be fair and well advised to have first his opinion on the question. Best regards, Shinkolobwe (talk) 13:49, 2 January 2011 (UTC)

FYI, according to: http://en.wikipedia.org/w/index.php?title=Special:WhatLinksHere/Template:Chembox_SystematicName&limit=500 About at least 300 pages (12 screens of 25 lines, if the counting is good) could be affected by the suppression of this template. So, be prudent! It is not a good idea! Once again, considerable time and work will be lost to correct the situation just to accomodate the desiterata of one single user. It would be beter to use this template simply with discernment and not to follow inflexible rules. Shinkolobwe (talk) 15:56, 2 January 2011 (UTC)

Chemicals for deletion

I have nominated Nitrofullerenes for deletion (Wikipedia:Articles for deletion/Nitrofullerenes) and proposed deletion of Octatetrazolylhydrazinecubane, two articles by the same new user. Any assistance in either verifying and saving these articles, or in concurring with the deletion arguments would be appreciated. ChemNerd (talk) 15:28, 3 January 2011 (UTC)

Cannot find any data for either on a reaxys search.  Ronhjones  ^(Talk) 20:43, 4 January 2011 (UTC)

If the articles will be deleted, we should not miss tagging the contained images for deletion. --Leyo 22:06, 4 January 2011 (UTC)

Images might be valid for theory (hypothetical structures). Materialscientist (talk) 22:24, 4 January 2011 (UTC)

Propadiene

The top image in the sidebar for Propadiene (edit | talk | history | protect | delete | links | watch | logs | views) seems to be incorrect (and inconsistent with the 3D rendering below it). The image in question is Image:Allene.png; the possibly-incorrect version was uploaded on 13 October 2010, and replaced a correct-looking previous version according to the file history. --Christopher Thomas (talk) 21:04, 9 January 2011 (UTC)

Wrong is a little bit too much, but with a that simple image the carbons should be added to improve the readability for no chemists. For a chemist the structure has to have three carbons, but this is not the case for non chemists. So lets go back to an imprved version of the image before 13 October 2010.--Stone (talk) 21:41, 9 January 2011 (UTC)

This was indeed an unfavorable replacement. --Leyo 21:43, 9 January 2011 (UTC)

I have reverted to the original version. -- Ed (Edgar181) 21:43, 9 January 2011 (UTC)

Timeline of chemistry potentially on Main Page

See Talk:Main Page#Featured content for a day Dabomb87 (talk) 23:09, 12 January 2011 (UTC)

I've had a quick look at the timeline of chemistry page, and am wondering what the inclusion criteria are, because there are some discoveries that I would have expected to see. Off the top of my head:

• the discovery of Zeise's salt, the first organometallic compound, circa 1830
• Mond's work on nickel tetracarbonyl producing an industrial process for refining nickel metal using organometallic chemistry, circa 1890
• the Dewar-Chatt-Duncanson model that finally allowed the bonding in compounds like Zeise's salt and nickel tetracarbonyl to be understood, opening up organometallic chemistry to systematic study, circa 1950s
• Lowry-Brønsted acid-base theory, the basic theory of acids and bases established in 1923 and still studied by every student of chemistry. Though not as powerful as Lewis acid-base theory postulated the same year, L-B theory is typically used unless Lewis theory is needed (ie. a bit like using Newtonian mechanics unless situations require invoking relativity)
• Nothing on room temperature ionic liquids despite them being used in industrial applications and displaying properties unlike other solvents... on which subject, green chemistry and the use of supercritical fluids might be worth mentioning. The 2005 Nobel Prize specifically recognised the contribution of green chemistry to metathesis processes.
• Ziegler-Natta methods for stereoregular polymerisation ('63 Nobel Prize) - as at 2010, industrial production using Ziegler-Natta catalysts exceeds 100 million tons annually, and as one of the largest production industrial chemicals in the world, surely it is important to the timeline of chemistry
• Fischer–Tropsch processes for the manufacture of hydrocarbons from CO and H₂ have a history going back to the 1920s, and have connections to present research on dealing with CO₂ and to migratory insertion reactions such as in the Monsanto and Cativa processes for manufacture of acetic acid by carbonylation of methanol
• Lonhort and Hodgkin's X-ray work in vitamin B12 system demonstrated a cobalt-carbon bond, showing organometallic systems extend into biochemistry in 1961, and led to medications like methylcobalamin
• No mention of the contributions of Sir Humphrey Davy, who discovered / first isolated sodium, potassium, calcium, magnesium, barium, and boron (from memory), demonstrated the Lavoisier's notions of acidity being due to oxygen was wrong (he showed that what we now know as hydrochloric acid contains no oxygen), and formulated a new theory of acids
• Nothing on Davy's greatest discovery, Michael Faraday who should at least be mentioned for his laws of electrolysis if not also for being the first to prepare and report on nanoparticles
• I notice that Volta is mentioned but Galvani is not
• no Walther Nernst of the 1920 Nobel Prize-winning work in thermodynamics, also known for the Nernst equation
• no Rowland, Molina, and Crutzen - Nobel Prize on ozone chemistry, understanding the Ozone hole, etc
• no Walter Haworth and his Nobel Prize-winning work on vitamin C and carbohydrate structures
• Discoveries like the Diels-Alder reaction and Grignard reaction would be on my list
• No mention of supramolecular chemistry, the so-called "chemistry beyond the molecule"

This is by no means meant to be an exhausitive list of corrections, and I recognise that there may be disagreement as to whether all of these should be in the timeline. Nevertheless, I suspect that other chemists will be able to produce other lists of potential omissions and am thus concerned about how complete this timeline actually is. Thoughts? EdChem (talk) 07:32, 13 January 2011 (UTC) PS: Further thoughts added. EdChem (talk) 13:47, 13 January 2011 (UTC)

The list has now been replaced by Moons of Saturn. In any case, it's probably a good thing that I mentioned it here; the list was promoted to featured list status in 2007, and I'm not sure that it has received much substantial editing since then. Dabomb87 (talk) 15:35, 13 January 2011 (UTC)

Given that the issue relating to the main page is now moot, and the stampede of comments here, I have opened a discussion at talk:Timeline of chemistry#Inclusion criteria and completeness. EdChem (talk) 08:44, 14 January 2011 (UTC)

More overspecialized categories

I have noticed that most of the subcategories in Category:Heterocyclic compounds (3 rings) have a very small number of articles in them (3 or less). These seem like overspecialized categories to me. If no one objects, I would like to empty many of them by moving the articles to more reasonable categories. Then I would like to tag them for deletion. Any comments? -- Ed (Edgar181) 20:08, 13 January 2011 (UTC)

Quite a few of the subcategories in Category:Heterocyclic compounds (2 rings) also have only one article in them. -- Ed (Edgar181) 20:11, 13 January 2011 (UTC)

I would also strongly argue the fact that do we need the "2 rings" / "3 rings" - as a lot of the compounds are not in the correct category - some users have counted the number of rings, some have counted only the number of rings with a hetero atom e.g in "2 rings" Asperlicin, Benzimidazoline, Ritanserin. It's a right mess. Let's drop the number of rings.  Ronhjones  ^(Talk) 23:23, 13 January 2011 (UTC)

In view of the recent problems with categorization, I would recommend that only certain editors be allowed to create categories. Say reviewers or rollbackers. I dont think that these standards would prove overly restrictive.--Smokefoot (talk) 23:43, 13 January 2011 (UTC)

List of hidden systematic names

As an illustration of my previous post, hereafter a list of hidden systematic names silently reinserted by Plasmic Physics without any explanation for some simple inorganic compounds (no Edit Summary, no discussion on the Talk Page !). These names are not directly visible on the pages, but are present in the code of the page. Why ? This was done after these systematic names were previously cleaned up, most often with motivation on the discussion page or here at WT:Chem and always with a clear statement in the Edit Summary.

List of some | SystematicName = <!-- Name 1 (substitutive) OR Name 2 (additive) -->.

Common name	Systematic name (substitutive)	Systematic name (additive)
Barium ferrate	Barium dioxoironbis(olate)	Barium tetraoxidoferrate(2-)
Beryllium carbide	Diberylliomethylidene	Diberylliumcarbon
Beryllium carbide	(Berylliumylidenemethylidene)beryllium	Beryllium methanide
Curium oxide	Curium(3+) oxidandiide	—
Prussian blue	Iron(3+) hexacyanoirontetrauide	Iron(3+) hexacyanidoferrate(4-)

What is the real intention behind these hidden (zombie ?) names ? What is the aim pursued ? I fear it is only the visible summit of the iceberg. Shinkolobwe (talk) 17:06, 16 January 2011 (UTC)

I have not noticed the extensive discussions here in the last few days.

The reason I add non-displayed names, are that I am tired of endless debates over the systematic names of chemicals. So for the time being, I hide them so that they may be decided at a later date.

As I understand, if a point is made and remains uncontested, all interisted parties are in agreement by default. This was the case on the deletion discussion, the closing statements by Beestra, the template's creator remained uncontested upto the closure of the discussion. One point he made, was that WP:OR is not a reason to delete a suggested systematic name, I agreed with this, and no one contested this.

People seem to overlook my other contributions to the chembox entirely, namely the properties, and hazard sections. --Plasmic Physics (talk) 08:47, 17 January 2011 (UTC)

The hidden sections might be acceptable. It is like in real life one bad thing erases 100 good things you have done.--Stone (talk) 10:47, 17 January 2011 (UTC)

I'm refering specifically to statements such as: "I have yet to see a constructive edit from plasma." by Smokefoot.

The systematic name oxidandiide is inadequate for oxide

Hereafter, a copy of the comment I left yesterday on the talk page of curium oxide after having discovered the last incongruity left there by Plasmic Physics in the chembox of this extremely rare compound.

| IUPACName = Curium(III) oxide<br\> | SystematicName = Curium(3+) oxidandiide

See the difference in editing here: http://en.wikipedia.org/w/index.php?title=Curium_oxide&diff=prev&oldid=407807816

The term oxidandiide cannot be found in the IUPAC Redbook 2005 (International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. Electronic version.).

In Table IX Continued, p. 319 (paper) or p. 331 (PDF) of the Redbook 2005, I can only find the following terms for oxide:

O^2–, oxide(2–); oxide

Oxidanide, a very rarely encountered chemical term, seems to have been attributed to the hydroxide anion (OH^–), but is never used in the practice by most of the chemists.

It is very strange that the term oxidandiide — such a crucial potential alternative term for oxide — would not have been explicitly described in the IUPAC Redbook 2005. The tentative deduction of "oxidandiide" from other terms also ending with the suffix "diide" in the IUPAC 2005 Redbook (from P-, S-, and Se-based compounds) without controlling the most common use of the term is a rigid and useless application of a non-validated rule. It seems that the IUPAC Redbook 2005 is itself still severely flawed. This is one of the most striking illustrations I have encountered yet.

I hope Plasmic Physics does not intend to rename all oxides as oxidandiides through the whole Wikipedia. :-(( Shinkolobwe (talk) 17:32, 16 January 2011 (UTC)

If the tumor is not cut out it will grow and we will have to live with nitro-oki-do-ki-do and potassium-diylium-2-oliolum. No one is verifying his other attributions. Is Plasmic Physics himself measuring and calculating with some coloured book? I had only a quick view on his last great work. He has measured the mass of plutonium hexafluoride very thoroughly and saw that it has a different colour than on webelements.com.--Wickey-nl (talk) 14:23, 18 January 2011 (UTC)

Chembot issue

@ Plasmic Physics; please do not remove extra }} like here - this makes chembot break articles, maybe Beetstra can comment on that too). Materialscientist (talk) 06:12, 16 January 2011 (UTC)

I do not remove the extra }}, the template displays correctly when I save an editted page. The bot removes the closing }} from the identifier section which corrupts the template. When you reinsert the }}, you are inserting it in the wrong place resulting in the lower part of the template not displaying. --Plasmic Physics (talk) 06:29, 16 January 2011 (UTC)

Ok, thanks, perhaps that }}}} should be split into 2 lines for now. Materialscientist (talk) 06:41, 16 January 2011 (UTC)

I confirm the problem: I had also to repair a similar problem in the chembox of curium oxide by adding a new set of lacking brackets }} at the end of the chembox. The problem can be observed here between the edit of Plasmic Physics and this of Chembot. Shinkolobwe (talk) 12:17, 16 January 2011 (UTC)

Noticed, indeed a bug. I will try and solve it one ASAP (I did not see now quickly why it breaks, it seems to have to do with the list of 4 closing curly brackets, I will try and reproduce the problem in debug mode.

As it does not do it when the 4 closing curly brackets are not connected (so either '}} }}', or two sets of '}}' on separate lines) I would suggest that if you notice them, please separate them (though it should be handled by CheMoBot properly).

Please leave notes on bugs on my talkpage, then I will react quicker. --Dirk Beetstra ^{T C} 09:54, 19 January 2011 (UTC)

I applied a patch/solution for this. Please notify me if the bot still breaks this . --Dirk Beetstra ^{T C} 11:40, 19 January 2011 (UTC)

Seemed to work in a test-edit. I am now simply splitting }}}} into two sets of }} on two lines before parsing. --Dirk Beetstra ^{T C} 12:28, 19 January 2011 (UTC)

Dibenzodioxin

I would like to get a third opinion on Talk:Dibenzodioxin concerning the naming of the article. Thank you. --Leyo 17:29, 19 January 2011 (UTC)

Plasmic Physics

I stumbled upon these two examples [1] [2] where I was reverted for vandalism. My question is: Plasmic Physics keeps on adding systematic names which have never been used in literature (see his recent edits). What should I do? It is not the first time of edit warring with him, and frankly the last thing I wish is to waste time on this matter. What is the position of the project on this? Materialscientist (talk) 05:33, 16 January 2011 (UTC)

A conclusion from Wikipedia:Templates for discussion/Log/2011 January 1 was that WP:OR is not a reason to remove a systematic name. This conclusion was uncontested. --Plasmic Physics (talk) 05:55, 16 January 2011 (UTC)

Nobody wants to delete a template which is transcluded to many articles. The issues are (i) if a chembox field is empty, it does not mean it must be filled up, (ii) as I understand IUPAC, names of simple (say binary) compounds do not follow systematic rules. I am more keen to hear first the opinion of the project, rather than of Plasmic Physics, on this whole issue. Materialscientist (talk) 06:41, 16 January 2011 (UTC)

Concur with Materialscientist and strongly disagree with Plasmic Physics's reading of the "conclusion" of the TFD. Just because someone said something as part of his/her rationale doesn't make that argument part of the consensus. The chembox template is a very general-purpose thing, designed to be able to accommodate all sorts of chemicals, and some things aren't very applicable to some cases. I'll say it plainly: wikipedia is about helping readers get information, not about showing off how well you can rigorously follow a rule even to cases where the rule does not necessarily (or citedly does not) apply. If an arbitrary reader wants to know a useless derived value from given data, he/she can just derive it. DMacks (talk) 14:37, 16 January 2011 (UTC)

I agree with the viewpoint of Materialscientist: as for his last edits, many of my recent edits dealing with systematic names of simple (say binary) inorganic compounds were silently modified by Plasmic Physics using a tactic to hide the changes he made: without any explicit mention in the Edit Summary (he always left it empty!), he reinserted in the chembox disputed systematic names using the syntax for hidden comments:
| SystematicName = <!-- Name 1 (substitutive) OR Name 2 (additive) -->.
See for example, what occurred here! with the very bad looking
| SystematicName = <!-- Diberylliomethylidene (substitutive) OR Diberylliumcarbon (additive) -->.
And there is still many other cases.

I do not understand the exact motivation behind this behaviour. For the moment, I can only imagine four reasons for acting so:

1. a great reluctance of abandoning intricate and lovely built systematic names which were rejected by the community ?
2. trying to feed the Wikipedia search system, or the Google robots, with these doubtful names in the hope of secretly advertizing them ?
3. a hidden agenda and a rampant tactic for resurrecting more easily these disputed names in the future ?
4. or, another unknown reason (maybe with a good intention, but then, it should be clearly explained to avoid any misunderstanding on the pursued goal) ?

In the case of a hidden agenda, such a tactic could be dubbed: creation of Zombie systematic names. Furtively re-inoculated names never die: they only sleep, awaiting to be reanimated when considered opportune.

If this hypothesis should be confirmed, this is not innocent and such a practice should be considered a highly disruptive behaviour. I do not understand the advantage of hiding systematic names. If they are good and useful, it is fine: simply show them. If they are problematic, the best is also to show them, so that they can be openly discussed with the community and improved. If they are wrong or useless, please simply admit it and desist.

Plasmic Physics, please listen and learn from the reactions of other users. You should realize that silently editing problematic systematic names in the back of many contributors cannot be considered a honest attitude. Indeed, it is not a good idea to wish (or to plan) to implement a particular idea without telling anybody. And please, also correctly fill the Edit Summary with an explicit comment clearly indicating what you are really doing. Your long history of edits considered disruptive and your recent initiative to nominate for deletion the Template:Chembox SystematicName do not argue in your favor.

I think that the present concern now deserves a user conduct RFC. Sorry if I misinterpreted the last edits of Plasmic Physics and if he has really another objective or a valuable reason for acting so: then it would be better that he clearly explains now his intentions to the community and what he really intends to do with these hidden edits.

Sorry if my patience is exhausted and if I have more and more difficult to discern good faith in these recent edits: I have lost enough time and work for controlling the veracity of these highly specialized and low-values contributions which are so misleading for the readers of Wikipedia. Shinkolobwe (talk) 16:27, 16 January 2011 (UTC)

Of course he should stop. For my interests in content, I have yet to see a constructive edit from plasma. Until administrators act, you will be forced to continue the janitorial work.--Smokefoot (talk) 17:04, 16 January 2011 (UTC)

Janissarial work perhaps, janitorial work NO, Thank You. Now administrators have sufficiently materials to act. Enough work and precious time diverted for Wikipedia. It is time to conduct a formal RFC procedure about Plasmic Physics and to definitely stop the damages and the time lost for all of us. Shinkolobwe (talk) 19:45, 16 January 2011 (UTC)

I've just removed a template regarding notability that Plasmic Physics applied to americium dioxide without an edit summary. It's a real pain checking their contribs to make sure nothing else had been inappropriately tagged thanks to the lack of edit summaries. Brammers (talk/c) 22:55, 16 January 2011 (UTC)

What I get out of this is, the users here wants the systematic name template to be used. Despite my entries being correct, they do not conform to your variable brand of correctness. You want proposed names to be discussed, yet you complain about having to bother with the effort. So, essentially you are telling me to stop contributing to systematic names, because you're tired of petty faultfinding. I'm not here to accomodate your citisisms, I am here to contribute to Wikipedia in a way which gives readers the information they are looking for. If a reader is looking for a systematic name, then they will have one. Critisisms, as with every other contribution, come second. --Plasmic Physics (talk) 07:32, 19 January 2011 (UTC)

what I read above is "I am right, I know what the reader wants, and I will go on no matter what others say". Is this what you really want? Can you clarify you motives? Why do you believe adding systematic names improves wikipedia? (nobody seem to use them, at least in inorganic chemistry) Materialscientist (talk) 07:51, 19 January 2011 (UTC)

I am right about what? As for what the reader wants, the template must exist for a reason. "Others" can't agree on what they want, other than to blacklist my contributions to chemboxes. The systematic names clears up ambiguity for some compounds for example, uranium hexafluoride is covalent molecule, whereas uranium trifluoride is ionic; or monomeric silicon nitride at STP is a polycyclic covalent molecule, rather than a branched linear molecule. --Plasmic Physics (talk) 09:37, 19 January 2011 (UTC)

Sigh, Plasmic Physics. Some compounds do have a use for that field, others don't. Some compounds do have a melting point, others don't. Some compounds are drugs, others not (so some do get the {{chembox pharmacology}}, others don't). Need I go on? And that is exactly what I meant in the deletion discussion. Do not make up your own interpretations, but ask and discuss.

Plasmic Physics, if there are so many editors trying to tell you that something that you do is not wanted, maybe you should consider to stop doing thát, and go on with the other things where there is no objection. Thanks. --Dirk Beetstra ^{T C} 12:21, 19 January 2011 (UTC)

Your logical does not follow, all compounds have systematic names. I did not make interpretations, I simply relayed what you said. If you're suggesting that I stop contributing to Wikipedia, then I suggest you have a look at three of the WP:Five pillars.

Blue pillar: Wikipedia is not... an experiment in anarchy or democracy...

Green pillar: Wikipedia has a neutral point of view. We strive for articles that advocate no single point of view. Sometimes this requires representing multiple points of view, presenting each point of view accurately and in context, and not presenting any point of view as "the truth" or "the best view". Editors' personal experiences, interpretations, or opinions do not belong here. When conflict arises over neutrality, discuss details on the talk page, and follow dispute resolution.

Yellow pillar: Wikipedia is free content that anyone can edit and distribute.

I know I follow these, do you? --Plasmic Physics (talk) 08:47, 20 January 2011 (UTC)

I know the pillars (I did not become an administrator here just because I asked a bureaucrat to flip my bit, you know) - Blue pillar: I am not experimenting anarchy or democracy, but I do see that many editors disagree with you - solution to that is NOT continuing, but to first discuss and convince them - Green pillar: if you suggest that not giving a systematic name is giving a POV to an article .. well. I do not think there is any dispute about neutrality of the pages, just about that certain additions of systematic names are OR, there are independent refs that call acetone by the systematic name 2-propanone, but applying the rules yourself and creating these systematic names (and especially where different applications of rules give different names, as is often the problem with inorganics) is not the way forward - Yellow pillar: yes, I did not say that you could not edit, but if there is discussion on a point, then it is not a solution to proceed, but to first discuss and finish that discussion (and as noted above, you do also a lot of good work, and I did not ask you to stop with that!). And maybe, if the discussion has many editors who disagree with you, then maybe, maybe it is better to just stop with that specific task. --Dirk Beetstra ^{T C} 08:59, 20 January 2011 (UTC)

Maybe it is time for you to start assuming some good faith with all the editors that have concerns with the edits you perform, and addressing the concerns and convincing them, in stead of defending yourself with the policies and guidelines. I know that I was just giving good advice in my post of the 19th of Jan, at 21:21 UTC. --Dirk Beetstra ^{T C} 09:00, 20 January 2011 (UTC)

Blue Pillar: I'm being blacklisted by democratic vote. To reiterate, I have made repeated attempts to discuss, but have received no constructive compromise or solution.

Green Pillar: Without consensus, denying a SN for an article that has clear provision, is nothing more than the advocation of a single POV. Again, without consensus, only retaining one SN when there are more, is disrupting the neutrality of the article.

Yellow Pillar: To be declined for editing the SN field has equal symbolism as to be declined for editing of any other part of the document. If the collective users cannot decide on an unambigous resolution concerning usage notes for the SN template, but instead vote to avoid the problem by simply blacklisting me, is not in the spirit of Wikipedia. If I am to quote someone, it is to "Throw the baby out with the water." <unsigned comment lef by User:Plasmic Physics>.

Sorry, I think you miss again the point. This has nothing to do with the main pillars of Wikipedia. It is a pure technical question dealing with ultraspecialised edits about systematic names (SN) of chemical substances that are most often useless and sometimes misleading for the reader.

Blue Pillar — You are not blacklisted by democratic vote. Many users simply request you to consider to stop doing such conflicting edits. Many examples have been given to illustrate you the more problematic cases, so that you can understand where and when it makes problem. The main concern is that it is very difficult to discuss with you. Most often there is no dialog: absence of answer or a response inexorably stating that you are right.

Green Pillar — There is no Point of View (POV), nor neutrality issue, about a name of a simple chemical compound. But when you invent systematic names which do not exist (as recently with curium oxidandiide for curium oxide or oxoazinic acid for nitric acid), you should understand that no one can agree that Wikipedia is polluted with non-existing chemical names or simply non-sense.

Yellow Pillar — Your allusion to symbolism ... . It is not because you are requested to be reasonable and more thoughtful when editing systematic names, that you cannot continue your positive contributions. Here again your statement about blacklisting is exaggerate. All is not purely black or white, yes or no, it is a question of nuances: some systematic names (SN) make sense, other not, and the field SN can be left empty if necessary, or filled with the best name(s) and not by all the names invented for the pleasure of inventing names.

The main concern arises from the fact that your numerous ultraspecialised and repetitive edits can affect a large number of pages in a systematic way, as you did when starting a very detailed categorisation effort based on names never used (and even non-existing such as, e.g., silanuide). Then the problem becomes systemic and can no longer be ignored. This is why it triggered so many reactions from other users and what could be called a kind of social control. Without such a control Wikipedia would simply not survive, nor have acquired its present level of notability. You should not underestimate the time and work invested by other contributors to cross-checked some of your edits and to communicate you their advices. Our only wish is that you could simply understand that "a claim is a gift" and take it into account. Shinkolobwe (talk) 01:34, 23 January 2011 (UTC)

We are infact, talking about the same thing. This is what I'm refering to: when an attempt is made to discuss, users keep redirecting the discussion off topic. I've lost count of how many times it has been mentioned that all SN are invensions by nature. It is not my responsibility to explain the IUPAC nomenclature used to make these so called nonsensical SNs, nor is it in my interest to advocate my POV on when, or which name I shall use; without consensus, I cannot possibly be expected to make those decisions indepently. I've ettempted numerous times to clarify the usage notes through discussion, only to have the topic avoided in every way possible. Users tell me to make my own decisions, but that is apparently what started the problem, so we keep going around in circles. That's why I need someway to standardize the usage notes. This is what I tried to say in my last post. --Plasmic Physics (talk) 02:33, 23 January 2011 (UTC)

I think that the main message is pretty clear and very consistent - the community of editors is pleading with you to stop editing ChemBoxes and stop editing nomenclature. --Smokefoot (talk) 02:49, 23 January 2011 (UTC)

The message is not very clear, read the above comments by Beestra. --Plasmic Physics (talk) 05:07, 23 January 2011 (UTC)

The message is very clear; you've been told enough times by enough people to stop adding systematic names. shoy (reactions) 14:01, 24 January 2011 (UTC)

Please read the thread before posting. --Plasmic Physics (talk) 05:27, 25 January 2011 (UTC)

OH groups in estradiol

User:Nirmos‎ and I disagree about the nature of the OH at C-3 of estradiol. The discussion is at User talk:Nirmos#Phenol or alcohol?. Nirmos‎' last post says (s)he doesn't care and I could do as I pleased, but I'd like some additional input before I undo their changes. I'd also like to know whether Category:Estradiols should be kept. It contains two pages and I could add perhaps one or two, but not more. Thanks, ἀνυπόδητος (talk) 10:57, 27 January 2011 (UTC)

Category:Estradiols does seem like non-useful/overly-specific cat. I was going to say "...so upmerge into parent Category:Estranes", but that cat looks like an orphaned sibling to Category:Estrogens. Therefore, I think cat:estranes should be merged into cat:estrogens. DMacks (talk) 11:19, 27 January 2011 (UTC)

I have commented at Nirmos' talk page. Estradiol is both an aliphatic alcohol and a phenol; this is a matter of fact. Just FYI.  :) EdChem (talk) 13:00, 27 January 2011 (UTC)

Thanks. I have nominated both for deletion/upmerge; see Wikipedia:Categories for discussion/Log/2011 January 27. --ἀνυπόδητος (talk) 13:51, 27 January 2011 (UTC)

Another one: Category:Phenols is a sub-cat of Category:Alcohols, which seems to be incorrect. Should I change that? --ἀνυπόδητος (talk) 15:11, 27 January 2011 (UTC)

It probably depends on which organic chemist you ask, but phenols are generally considered a type of alcohol, and they fit the definition given in the first sentence of alcohol. But because they have some distinct properties, such as increased acidity, they are often considered separately. -- Ed (Edgar181) 16:14, 27 January 2011 (UTC)

(ec) It's crazy...most organic chemists I know consider phenols as "aromatic alcohols", but it's not technically (Gold Book) correct. According to IUPAC def of alcohols, the C must be saturated, which eliminates phenols and enols as being alcohols.That would mean Category:Phenols should be a sister cat of Category:Alcohols within Category:Oxygen compounds, not a subcat of it. But then the IUPAC definition of enols says that they are alcohols (even though C is not saturated)! Maybe have cat:phenols both as a subclass and sister class of cat:alcohols (per technical def but also common usage)? DMacks (talk) 16:29, 27 January 2011 (UTC)

Phenols says (2nd sentence) that they aren't alcohols. Perhaps it should be changed to say that classification varies, to avoid contradiction with Alcohol. I have no source to support the alternative view, though. --ἀνυπόδητος (talk) 17:18, 27 January 2011 (UTC)

From my experience, this really is one that can go either way. I don't think it would be wrong to classify phenols as alcohols. Saying that the classification varies is probably a good way to go. ChemNerd (talk) 21:01, 27 January 2011 (UTC)

Systematic Name

Protactinium(IV) oxide requires a systematic name, User:Stone removed both substitutive and additive names:

• Dioxoprotactinium
• Dioxidoprotactinium

Which one should be restored? --Plasmic Physics (talk) 10:12, 26 December 2010 (UTC)

None of them: only the oxidation state is important for the speciation of protactinium (IV or V) and it is only interesting for nuclear chemists and specialists of the migration of radionuclides in the geosphere (highly specialized audience well aware of the chemistry of this element (a nasty alpha emitter) and which does not pay more attention to nomenclature than what it is worth). Overspecialized nomenclature is useless. Shinkolobwe (talk) 00:00, 29 December 2010 (UTC)

Irrelevant, the entry is empty and needs to be filled. --Plasmic Physics (talk) 03:46, 31 December 2010 (UTC)

All empty entries in Chemboxes do not necessarily require to be filled. It also depends on appreciation and priorities. Moreover, there exist several millions of different molecules inventoried in chemical databases. All our lives here at the Chemicals Project are not sufficient to cope with such a giant task. We need to focus on the essential. Shinkolobwe (talk) 16:08, 31 December 2010 (UTC)

Sodium amide requires a systematic name, User:Shoy removed both substitutive and additive names:

• Sodium azanide (substitutive)
• Sodium dihydridonitrate(1-) (additive)

--Plasmic Physics (talk) 03:46, 31 December 2010 (UTC)

Please cite a source which gives exactly that name, and please do not use OR source like IUPAC.--Stone (talk) 08:33, 31 December 2010 (UTC)

Beryllium oxide requires a systematic name, User:Shoy removed both substitutive and additive names:

• Beryllio-λ1-oxidanyl (substitutive)
• Oxidoberyllium(2•) (additive)

--Plasmic Physics (talk) 03:46, 31 December 2010 (UTC)

Please cite a source which gives exactly that name, and please do not use OR source like IUPAC.--Stone (talk) 08:33, 31 December 2010 (UTC)

Disiloxane requires a systematic name, User:Shinkolobwe removed both substitutive and additive names:

• (Silyloxy)silane (substitutive)
• μ-Oxido-bis(trihydridosilicon) (additive)

--Plasmic Physics (talk) 03:46, 31 December 2010 (UTC)

Please cite a source which gives exactly that name, and please do not use OR source like IUPAC.--Stone (talk) 08:33, 31 December 2010 (UTC)

An impossible request, there are no reliable sources garuanteed to conform to IUPAC nomenclature recommendations (excluding examples from IUPAC actual). This was established in earlier discussions. --Plasmic Physics (talk) 08:58, 31 December 2010 (UTC)

Plasmic Physics - The consensus amongst the Chemistry community here on WP is that none of these names need to be replaced. They are at best irrelevant (nobody uses them), and they are inappropriate (see the next thread). Furthermore, because you are creating them by the application of a complicated set of rules there is no guarantee that they are correct. We have to be careful here on WP because of the ever-increasing popularity of the site and its use as a reliable source (particularly by undergraduates writing lab reports), and the danger is that your actions lend legitimacy to these names. You need to realise that just because IUPAC has mandated a set of rules for the naming of chemical compounds, that does not mean that chemists use or even accept them. These pages have all been built by working chemists according to naming and classification schemes that reflect those used in working chemical laboratories, and it works. Your attempt to impose IUPAC nomenclature on the chemistry wikiproject has resulted in an awful lot of man-hours being spent undoing it.

People are getting annoyed. Please desist. Whilst I do not doubt that your efforts are in good faith, your edits in these areas are creating problems rather than contributing constructively. Thanks, Chris (talk) 09:11, 31 December 2010 (UTC)

There is nothing non-systematic about compositional or Stock nomenclature. Plasmic Physics should go and read International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. Electronic version.. Then read it again. And again. Until he understands it. Until such time, he should refrain from editing articles about chemical substances. Physchim62 (talk) 16:32, 31 December 2010 (UTC)

Systematic name of ammonium bifluoride

Plasmic Physics - Please, listen. What Chris has just said hereabove is very important and well thought. Because of the increasing notoriety of WP, the intricate and inappropriate systematic names you continue to introduce for simple inorganic compounds are potentially very misleading for ungraduate students and inexperienced users. A supplementary example you just edited today are the systematic names for ammonium bifluoride.

SystematicName = Ammonium difluorohydrogenuide (substitutive)

Ammonium difluoridohydrogenate(1-) (additive)

see diff here

It makes absolutely no sense for a simple inorganic compound:
NH₄HF₂ is nothing else than NH₄F · HF and it certainly does not deserve these systematic names, particularly ammonium difluorohydrogenuide: it is wrong and should it be correct, it is never used.

Listening and taking into account advices and critics from their peers is fundamental for all scientists and is integral part of the scientific approach. Please, adopt a more open attitude and also observe how others work. Judicious observation in chemistry and science is more important than pure deduction, certainly from rigid rules. Shinkolobwe (talk) 12:46, 31 December 2010 (UTC)

If the entry is irrelevant, inappropriate, and unsourceable, then I propose that such a useless entry be deleted. --Plasmic Physics (talk) 21:15, 31 December 2010 (UTC)

Dear Plasmic Physics, thank you for your answer. Best wishes for 2011. I just made again a verification of the systematic names you proposed for ammonium bifluoride. Hereafter the results of a quick Google search:
* Ammonium difluorohydrogenuide: 1 result; it only links to the substitutive systematic nomenclature name you added yourself to the chembox of ammonium bifluoride on Wikipedia.
* Ammonium difluoridohydrogenate: 11 exact results rendered from about 29 total results (very few results and most often pointing to unreadable pages with long scrolling lists).
In both case, Wikipedia was listed at the top of the search results. This illustrates the considerable power of a single edit made on Wikipedia: it has a very high impact on the results from a Google search and is proposed to the reader in the first place. That is why edits dealing with chemical nomenclature or systematic IUPAC names are not anodine and have to be done with great care and more circumspection. Incorrect and misleading so-called systematic IUPAC names could rapidly acquire a high popularity amongst undergraduate students if they lack of critical mind and believe all what they read on Wikipedia. It could result in a poor evaluation at their exams and a loss of credibility for Wikipedia in general and the Chemistry Portal in particular. Hereafter, the result of a search for Ammonium bifluoride on PubChem Compound: http://www.ncbi.nlm.nih.gov/pccompound?term=Ammonium%20bifluoride

Ammonium difluoride;
Ammonium hydrofluoride;
Acid ammonium fluoride
IUPAC: azanium fluoride hydrofluoride

CID: 14935 links to several synonyms (37 in all) at: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=14935&loc=ec_rcs.
Amongts all the synonyms in the list, I could not find the two systematic names (additive and substitutive) you derived from your own understanding of the IUPAC rules.

Interestingly, as illustrated by a figure presented here on the site of Pubchem, ammonium bifluoride is a compound with a very strange crystallographic structure: its crystal lattice contains a mix of ammonium and fluoride ions with neutral undissociated molecules of hydrofluoric acid. I understand it like if HF was playing the role of water molecules in the crystal lattice of a salt. It is a little bit like if NH₄F was hydrated with neutral HF molecules. Or could it be seen as a clathrate with non-dissociated HF molecules trapped in the cage of ammonium fluoride. I am happy to have discovered that today (yesterday, I thought that HF was dissociated in H⁺ and F^– ions in the crystal lattice of this compound) :-).
As you agreed just hereabove, I will also suppress the two inappropriate systematic names from the chembox of ammonium bifluoride. Thank you for your answer and the discovery of this unusual crystal lattice. Appreciated. Best regards, Shinkolobwe (talk) 15:42, 1 January 2011 (UTC)

Outcomes of supplementary controls

After better understanding the exact – and more complicated than initially expected – nature of the quite unusual HF₂^– species present in the ammonium hydrogen difluoride, and after an interesting discussion with Smokefoot on the subject, I started to doubt about the incorrect character of the systematic names proposed by User:Plasmic Physics. To avoid to be unjust or inequitable for him and also to avoid to possibly throw the baby with the water of the bath, I continued to search for these systematic names for ammonium bifluoride in the IUPAC 2005 Redbook. Hereafter, the results of my last searches which are also consistent with my previous searches with Google: an additive systematic name is well possible and confirmed by the IUPAC 2005 Redbook (however, 11 or 37 occurrences only can be found with Google!), but no substitutive name can be derived or confirmed (zero occurrence with Google and in the 2005 Redbook) (cfr, our previous discussion on the question in the next section of this talk page).

According to International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. Electronic version. (Table III continued, p. 268 in the PDF, p. 256 on paper), the suffix "uide" is defined as follows:

"uide": suffix specifying the addition of hydride to a parent structure, accompanied by locants and multiplicative prefixes if appropriate, e.g. tellanuide, TeH₃^–.

There is clearly no hydride (H^–) present in the bifluoride anion which only contains one central proton sandwiched between two fluoride anions: F^– … HF or F–H–F^– or HF₂^–. So, clearly, this unusual anion in which a strong hydrogen bond is gluing together a small fluoride anion and a non-dissociated HF molecule cannot be named difluorohydrogenuide and it also explains why no substitutive systematic name is given by IUPAC for the hydrogen bifluoride anion.

However, the additive systematic name difluoridohydrogenate(1–) is well given as an example in the IUPAC 2005 Redbook: see item 20 (HF₂^–) in the section IR-7.3 on "Additive Nomenclature", p. 126 in the PDF file, and p. 114 on the paper hardcopy.

However, I would also suggest to omit this additive systematic name from the chembox of ammonium bifluoride because the notion of hydrogenate is very rarely encountered in chemistry, not widely adopted amongst the chemistry community, and most importantly, to avoid to confuse the audience and to be misleading for the inexperienced students.

Sorry to have been so long in these explanations for this very particular case involving the quite uncommon chemical bond F^– … HF. Best regards, Shinkolobwe (talk) 22:51, 1 January 2011 (UTC)

Conclusions

As concluding remark, the control of such unusual systematic names is very tedious and requires too much time and energy that could be better allocated to other more interesting or productive works. Errors in writing, or controlling, such rare systematic names can be easily done in perfect good faith by anyone of us. I think it is a supplementary valuable reason to omit them when not necessary for describing simple inorganic compounds. I do not speak here about organic substances for which it can help describing the topology of functions and groups present in complex molecular structures. Best regards, Shinkolobwe (talk) 22:28, 1 January 2011 (UTC)

Fundamental asymmetry of forces at work

Many inorganic compounds with simple structure still carry the stigmates of a frenetic renaming activity that occurred during the summer 2010 and many more perhaps still remain to be discovered. Simply, look at what link to the Template:Chembox SystematicName to trace such dubious, as useless, names for simple inorganic compounds. And all problematic edits are systematically pointing to one single contributor, as here.

Did the following simple inorganic compounds really deserved such esoteric systematic names?

• Aluminium carbide:

| SystematicName = Tetraaluminium(3+) tetramethanetetraide

• Beryllium carbide:
  

| SystematicName = (Berylliumylidenemethylidene)beryllium

| SystematicName = Diberyllium(2+) methanetetraide

| OtherNames = Beryllium methanide

• Silicon nitride:
  

| SystematicName = 1Si-Hexacyclo[3.1.1.0^1,4.0^2,5.0^3,6.0^3,7]trisilazane

• Germanium disulfide:
  

| SystematicName = Germanedithione

• Prussian blue

| SystematicName = tetrairon(3+) tris(hexacyanoirontetrauide)

:-((     Shinkolobwe (talk) 00:30, 10 January 2011 (UTC)

In the meantime, other non-sense systematic names such as azinic acid (HNH₂O₂ = NH₂O(OH)) erroneously introduced by Plasmic Physics as systematic name for nitrous acid (HNO₂) have also been corrected (see talk page). Shinkolobwe (talk) 00:08, 9 January 2011 (UTC)

So, the lifetime of highly specialized but inappropriate contributions can be relatively long because they remain easily undetected, or that the readers are abused by their complexicity and do not dare to correct them. There is a fundamental asymmetry of forces at work. It is, in fact, much easier to make allegation to esoteric or kryptic names than to track down them with sufficient reasonable explanations to verify what they really mean. Wikipedia is very weak and poorly equipped to self-protect with respect to such persistent disrupting behaviour. :-( Shinkolobwe (talk) 02:26, 9 January 2011 (UTC)

Silicon nitride looks pretty bad. As usual, these chemicals are stoichiometric formulas for larger-scale structures, not simple covalent units. And this one even has three phases that appear to have different connectivities. As usual, the article itself contradicts the proposed naming scheme. DMacks (talk) 22:21, 9 January 2011 (UTC)

Sanity alert

"Ammonium difluoridohydrogenate(1-)"? Gosh!
Folks, please note that Wikipedia is directed to chemists. It is not meant to replace chemical reference works, much less to be a battle ground for nomenclature addicts. Articles must be readable by non-chemists and must be easily edited by chemists. So please let us focus on adding interesting contents, rather than obscure nomenclature that is of no use to anyone.
From that viewpoint, chemboxes were a colossal mistake, and are one of the reasons why the body of active editors is shrinking. I have 2000 articles in my watchlist, but most edits in the past two years have been pointless cosmetic fixes --- including many pointless chembox edits.
Remember, Wikipedia is not a database! Creating a database of chemical compounds requires much more effort, and much better tools, than we have now.--Jorge Stolfi (talk) 12:14, 30 January 2011 (UTC)

Sodium chloride graph

Hi. I have created a graph (File:Saltwater freezing point.jpg) for a property of NaCl. It compares the freezing point temperature and salinity of brine, using existing data in the article, and the dataset ends just before reaching the maximum solubility of salt in water at 273K. Please verify that the original table data is correct, and add a citation to that information if necessary, for I will be adding the graph to article momentarily. Thanks. ~AH1^(TCU) 20:11, 22 January 2011 (UTC)

I have updated both the graph and table, here and in sodium chloride. The table which you used was unreferenced and incorrect. Materialscientist (talk) 07:39, 24 January 2011 (UTC)

stupid question, but what happens below where the green line bounces off the black line —Preceding unsigned comment added by 70.180.238.179 (talk) 00:26, 27 January 2011 (UTC)

A mixture of solids. See a more detailed phase diagram, e.g. here. Materialscientist (talk) 00:46, 27 January 2011 (UTC)

Compare to this. ~AH1^(TCU) 21:38, 2 February 2011 (UTC)

Do we need categories at all?

I was trying to avoid the issue, but must ask now: what is the point of the category system? Do readers actually use category pages? What can we get out of categories that cannot be obtained from master articles (like monosaccharide) or "List of" articles? We will never figure out the "right" category for oxalyl chloride if we don't know the answer to this question.
All the best, --Jorge Stolfi (talk) 11:55, 30 January 2011 (UTC)

I find many categories too full, too cluttered, or too strangely arranged to be of use. But they are often really useful: when I want to find all the articles about, say, gadolinium compounds, or imines, or whatever. I use them to find articles I didn't know existed and didn't think of searching for. Then I add any useful content I can, or just read the articles for interest.

On Commons it's especially useful, because categories get so full so quickly, and searching for files with keywords is hit and miss because people have so many different names for the same molecules/reactions/substances.

I added a lot of organo-main group content to Commons a while ago, and I found it much easier to categorise things as, say, "phosphorus-nitrogen compounds", or "boron-fluorine compounds", than to put related compounds in totally different categories depending on whether they have an organic part or not.

One thing I often do is have a master category like "silanes" and a subcategory like "organosilanes". "Organosilanes" also goes in "organosilicon compounds". That way you have inorganic silanes in the master category, organosilanes close by but separate, and you don't end up with inorganic silanes as a subcategory of "organosilicon compounds".

For Wikipedia, maybe we have something like this:

Carbon tetrafluoride ∈ Category:Carbon tetrahalides ∈ Category:Binary compounds of carbon ∈ Category:Carbon compounds ∈ Category:Chemical compounds by element ∈ Category:Chemical compounds.

Similarly for all the oxocarbons:

Mellitic anhydride ∈ Category:Oxocarbons ∈ Category:Binary compounds of carbon etc.

And perhaps:

Urea ∈ Category:Carbon compounds without C-H bonds ∈ Category:Carbon compounds etc.

Ben (talk) 12:48, 30 January 2011 (UTC)

• I can believe that categories are useful for the Commons, since the textual descriptions of files are too skimpy and there is no equivalent of "master articles". But are categories really useful in article space? The example you gave (gadolinium compounds) can be satisfied by searching for "gadolinium", or by a "List of gadolinium compounds", or a section in gadolinium.
  I believe that the accessory frills and machinery (like categories, infoboxes, stub tags, editorial tags, navboxes, wikiprojects, assessment efforts, etc.) have grown to the extent that they are smothering wikipedia proper. Our human resources are not sufficient to clean up articles; why should we squander them in the vain attempt to build those secondary structures? (Vain, because we clearly don't have the resources needed to complete any of those goals.)
  I ask again: if all category tags were deleted overnight, would readers really miss them? All the best, --Jorge Stolfi (talk) 14:14, 30 January 2011 (UTC)

Maybe you're right (to an extent - let's not just delete all categorisation unilaterally!), but it would be nice to have some way of navigating a list of all our compound articles. A quick road map, with all existing articles listed, rather than the (understandably) selective coverage in individual element articles. I might make such a thing in my userspace and see if it's any use. I'll probably do it by element but we'll see what's possible.

Ben (talk) 08:45, 31 January 2011 (UTC)

• Sure, the idea of junking the category system at this point is utopic, so this is mainly an idle discussion.
  Some of the presumed advantages of the category system are realized only if all articles have all tags that are relevant to them. With the help of robots, we may perhaps reach a state where almost every article has at least one category tag. But no robot can help us find articles that need additional tags. As mentioned above, formic acid can be viewed as an aldehyde, an alcohol, a carboxylic acid, and an hydrate of CO (and also as an anhydride of orthoformic acid). More categories are needed to cover the formate anion and the class of organic formates. Then we have categories of usage, hazard, environmental impact, and so on. A complicated drug molecule can easily require several dozen category tags.
  The point is that there is no chance that we can ever find and fix all under-categorized articles. But then one cannot trust the category system when looking for all articles of a certain topic. If you start from Category:oligomers, for example, you will never get to cyclopentanepentone --- even though the article explicitly describes it as a pentamer of CO.
  When looking for all articles on some arbitrary topic, the search tool will, almost always, give a more complete result than the category system. Moreover, the search tool can provide the intersection of two or more categories, e.g. "alcohol chloro" to find all articles on chlorinated alcohols --- a search that the category system does not support.
  Moreover, a topic can be listed in a category page only if the corresponding article exists. In contrast, a master article (or list-of article) can list all known members of the category, even if they do not have articles yet. This idea works fine, for example, for articles on genera and other biological taxa, such as Trigona or Lacrymaria (ciliate), and for certain chemistry articles such as monosaccharide or heptane.
  Unfortunately, when the category system was introduced, no one thought about these issues. As in many other Wikipedia sub-projects, its proponents could see only its advantages; no one stopped to evaluate its costs, or even if it could be successfully implemented at all.
  So, that is why I have little interest in categorization issues...
  All the best, --Jorge Stolfi (talk) 07:00, 2 February 2011 (UTC)

There is one good example for a category we simply do not need: Benzenehexols We should delete it.--Stone (talk) 10:33, 2 February 2011 (UTC)

Many organic compounds only have one functional group and are easy to categorise. Formic acid is more a carboxylic than an aldehyde because most aldehydes do not have a single bond to oxygen. Acetaldehyde, propionaldehyde, butyraldehyde (and so on) are all clearly aldhydes. I think Category:Aldehydes containing these simple examples is useful. But formic acid shouldn't be in it. Drugs molecules are a nightmare and I think it makes little sense to categorise them based on all their functional groups - we just get functional group categories full of polyfunctional molecules.

The problem is, because categories exist, people want to populate them with every example. This, as you point out, is (i) a never-ending task and (ii) often unhelpful. If we could search for articles based on molecular structure, that would be far superior.

Ben (talk) 15:45, 2 February 2011 (UTC)

Discussion about stubs

Here a discussion about stubs.--Wickey-nl (talk) 17:38, 3 February 2011 (UTC)

Category Resurrection

Category:Hydrosilicons was previously deleted as per WT:Chem discussions. The category has recently been resurrected by User:Kupirijo under a new name: Category:Silicon hydrides. Plasmic Physics (talk) 05:10, 9 February 2011 (UTC)

Category:Silanols was previously deleted as per WT:Chem discussions. The category has recently been resurrected by User:Kupirijo under the same name. Plasmic Physics (talk) 05:13, 9 February 2011 (UTC)

hexacyanochromate(II)

Is this a mistake? I can find many literature references to hexacyanochromate(III) (CAS#14875-14-0), but not hexacyanochromate(II). Can someone else take a look? ChemNerd (talk) 20:39, 9 February 2011 (UTC)

I added a ref to the article that seems self-consistent for this complex (i.e., not a typo). It doesn't seem notable enough for its own article, but the pentacyano might be (unusual spin characteristics--see same ref I added to this hexacyano article) so could mention it in there. Even back to the article's origins, WP-chem folks raised concerns that its creating editor was making stubs for lots of non-notable chemical species. DMacks (talk) 21:01, 9 February 2011 (UTC)

Thanks for taking a look, DMacks. Based on the abstract of that article, I think hexacyanochromate(II) may not be of much interest. But there are literally hundreds of references to hexacyanochromate(III) complexes that can be located by SciFinder. Should the article be renamed/rewritten to correspond to the far-more-notable of the two? ChemNerd (talk) 21:15, 9 February 2011 (UTC)

Not renamed/rewritten-about-something-else, because this article at this name really is about this topic. But certainly could push to delete it and obviously no harm in working on an article about something-else at something-else's-name (i.e., de novo on new topic, not transforming a different topic's page). DMacks (talk) 21:26, 9 February 2011 (UTC)

The compound is known but pretty esoteric. So unless anyone objects, I propose that I revise the article to include it but refocus/rename/move it to K3Cr(CN)6, which is the basis of 124 journal hits on CAS. The revised article would mention the tetraanion.--Smokefoot (talk) 01:54, 10 February 2011 (UTC)

Ipratropium

There is a discussion at Talk:Ipratropium about whether this should be the bromide form or not. 64.229.101.183 (talk) 23:46, 14 February 2011 (UTC)

Requested page moves

If anyone is interested in contributing to the discussion, an anonymous editor has proposed moving acetone and isopropyl alcohol to their IUPAC names. See Talk:Acetone ‎and Talk:Isopropyl alcohol. ChemNerd (talk) 17:42, 17 February 2011 (UTC)

How to represent amino amino acid structures

There's a question of a generally-relevant nature at Talk:Amino acid#Overemphasis of the neutral form. DMacks (talk) 19:18, 19 February 2011 (UTC)

Metalate or metallate

Is it metalate or metallate? Just wondering because I started an article on cyanometalate, but maybe it should be cyanometallate.--Smokefoot (talk) 14:11, 11 February 2011 (UTC)

this is engvar, pick one and don't worry —Preceding unsigned comment added by 70.189.170.229 (talk) 19:22, 22 February 2011 (UTC)

Dinitrogen

An edit is repeatedly reverted with nonsense arguments. Of course with the help of Plasma Physics.--Wickey-nl (talk) 09:28, 26 February 2011 (UTC)

...And Christian75. Plasmic Physics (talk) 09:54, 26 February 2011 (UTC)

Inorganic chemists like to be precise and call it dinitrogen, dioxygen, dihydrogen, to distinguish it from the atom or substituent. I suppose context is key. --Rifleman 82 (talk) 16:35, 26 February 2011 (UTC)

Yes, I agree. When used in the context of coordination chemistry and organometallic chemistry, dinitrogen (dihydrogen, ...) is common and useful way of distinguishing atomic and molecular forms of these molecules. In general, though, calling nitrogen gas dinitrogen seems cumbersome. Worse, dinitrogen would confuse readers, which is something to avoid. --Smokefoot (talk) 16:51, 26 February 2011 (UTC)

...Which Wickey-nl was told three times over in the reversion summaries. Plasmic Physics (talk) 22:56, 26 February 2011 (UTC)

Inorganic vs. Organic

Unresolved

We need to define conditional rules which, determine how to add categories or stub templates for carbon containing compound articles i.e., oxolate salts, mellitic anhydride, etc.

One possible condition:

Let Q equal a hetero atom, excluding C or H

If the compound contains a C-H, or a C-Q-H moeity, then the compound equals organic, else it equals inorganic.

Thus, oxalic acid is organic, oxalate salts are inorganic; or carbonate is inorganic, bicarbonate is organic. --Plasmic Physics (talk) 00:14, 30 January 2011 (UTC)

This approach is not conclusive. Bicarbonate and carbonate are both inorganic species whose relative distribution in aqueous solution only depends on pH. It makes no sense to claim that carbonate is inorganic while bicarbonate should be organic because it simply bears a proton more. Similarly, why should the simple abstraction of a proton from oxalic acid suddenly transform oxalate in inorganic compound.

Many organic compounds also only contain C-C bonds and C-Q bonds. Some examples:

• Carbon tetrachloride;
• Hexachloroethane;
• Tetrachloroethylene;
• Chlorofluorocarbon;
• Halon;
• Polytetrafluoroethylene (PTFE, Teflon);
• and more, ... .

According the hereabove mentioned definition, all these compounds should be ... inorganic!

Why should also carbon tetrachloride be inorganic while chloroform is organic. Because it is the product of the last step of the chlorination reaction?

Where to place phosgene (Cl-CO-Cl) and phosgene iminium (Cl-CNH-Cl) ?

Some silicon-containing compounds have also many analogies/similarities with their carbon-equivalent cousins and the synthesis techniques are these of organic chemistry.

A compound containing a C-H bond is necessary an organic compound, but it is not a sufficient condition to define an organic compound. For instance, oxalate (COOH)₂ and urea (H₂N-CO-NH₂) do not contain C-H bond, but both are clearly organic compounds.

Shinkolobwe (talk) 01:20, 30 January 2011 (UTC)

I agree with Shinkolobwe: a precise definition is a hair not worth splitting. Talk:Organic compound summarizes previous discussions. So I recommend laxness.--Smokefoot (talk) 01:34, 30 January 2011 (UTC)

Indeed, it makes no sense to attempt to draw an arbitrary frontier between organic and inorganic chemistry (and compounds). The best is to follow with flexibility the most common practices used by chemists in the literature and simply to adhere to the common usage with good sense. Shinkolobwe (talk) 01:45, 30 January 2011 (UTC)

We could create a category called Category:Organic-inorganic borderline compounds for the grey area, to include subcategories such as carbon tetrahalides.

Ben (talk) 02:03, 30 January 2011 (UTC)

It is just a preliminary suggestion. By your reasoning carbon dioxide would be organic, because it is the last step of glucose metabolism? Who is to say that carbon tetrachloride is organic? It doesn't even follow organic nomenclature.

Smokefoot:The problem can't be wished away, because there will always be a need for stub templates.

Shinkolobwe: It makes very good sense to set an arbitrary frontier, to solve this very problem. Look at nanoscience, there is an agreement that dimensions smaller than 100 nm falls within the domain of nanoscience, only one nanometer makes the difference.

Banjah-bmm27:That just renames the same problem, then we have to find a way to sort the article into the right category, what would qualify an article for your proposed stub template? --Plasmic Physics (talk) 03:07, 30 January 2011 (UTC)

I agree with Shinkolobwe and Smokefoot, arguing about edge cases is a huge waste of time. Ben, I fear your idea would just promote arguments about what is (or is not) an edge case. For example, Plasmic Physics asks about mellitic anhydride which I would consider a clear organic compound (aromtic benzene ring in the centre), yet it is composed of only carbon and oxygen. Would that make carbon monoxide organic? If not, what about O=C=O, O=C=C=C=O, and O=C=C=C=C=C=O? Carbonate is generally considered inorganic, but what about carbonic acid - each differs from the hydrogencarbonate ion by one proton, so should they all be categorised the same (and hence inorganic? What about something like dimethyl carbonate? I would consider CCl₄ as a clear organic compound, it's the logical outcome from sequential chlorination of methane, but that too could be argued. If tetrachloromethane is inorganic then what happens to phosgene? If we want a C-H or C-C bond then how do we decide on chloroformic acid, or 5-aminotetrazole? This could go on and on and on and on and on (and on). I realise that expertise is worth little on wikipedia, but unfortunately this really is an area where chemists know what is organic when they see it (with apologies to Potter Stewart) and anyone who can't figure out what is what would best contribute by deferring to those who can. To put the argument in more wiki-politcally acceptable terms, highly respected reliable source offer working definitions with slight variations and then add a caveat that there is disagreement around edge cases, and I can think of no reason for us to adopt any approach different from those sources. EdChem (talk) 03:12, 30 January 2011 (UTC)

I doubt textbooks all agree on whether CCl₄, for example, is organic or inorganic. Hence it is on the organic-inorganic borderline.

I think it would help to confine contentious examples to one place where we can find them. Carbon compounds with no C-H bonds would go here. Perhaps with specific exceptions: CO₂, carbonate salts, cyanide salts as these have been widely known and used for many years and universally considered inorganic. There won't be arguments if we define specific criteria for edge cases.

As far as I'm aware, carbonic acid is universally considered inorganic as it has no C-H bonds, and is formed by the reaction of CO₂ and H₂O, both inorganic compounds. Dimethyl carbonate is definitely organic as it contains C-H bonds.

I imagine more textbooks and papers than not would call phosgene organic, but it could quite legitimately be considered inorganic, as many other oxychlorides are, and it lacks C-H bonds. Urea, despite being a similar molecule, is probably universally considered organic, but that's probably because it is made in large quantities by organisms.

Ben (talk) 03:39, 30 January 2011 (UTC)

See also: Category:Inorganic carbon compounds and Category:Carbon compounds for the current state of categorisation.

Ben (talk) 03:41, 30 January 2011 (UTC)

• Frankly, do we *need* a definition? If this discussion shows anything, is that there is no clearcut distinction between the two classes. So why do we need to invent a split for which there is no consensus in the field?
  The names have only historical meaning anyway, and they persist today only in the administrative structure of academic departments: rather than organic and inorganic chemicals, the split seems to be between organic and inorganic chemists, each with their society of teachers, advisors, journals, and so on. The difference seems to be largely about which instruments and reagents one finds on scientist benches --- chromatographers instead of electric furnaces, aqua regia instead of methanol, etc.
  I think that Wikipedia can work fine without a definitive choice on this issue, in the same way as it wisely avoided taking a stance on the British/American spelling question. Namely, let each editor classify each article as he sees fit. When in doubt over "organic chemical" or "inorganic chemical", just write "chemical" and move on. Disputed articles may be classified either way, or both ways. In any case, let's not waste time arguing about the choice. All the best, --Jorge Stolfi (talk) 05:30, 30 January 2011 (UTC)

Have you read the introductory paragraph? --Plasmic Physics (talk) 07:27, 30 January 2011 (UTC)

Ben has a point, the current categorisations include some highly questionable examples:

• The inorganic carbon compounds category (hereafter ICC) contains the article on oxalyl fluoride, F-C(=O)-C(=O)-F, but the article is described as an organic halide stub and categorised as an acyl fluoride, a category which is itself a sub-category of organic compounds
• ICC contains the article on cyanamide, the article begins "Cyanamide is an organic compound with the formula CN₂H₂". It is a member of the category cyanamides which is itself a sub-category of organic compounds
• ICC contains the article on phosgene which the article tells us is a valuable "industrial reagent and building block in synthesis of pharmaceuticals and other organic compounds". As a member of the acyl chloride category, it is a sub-category of organic compounds
• ICC contains the article on tetrabromomethane which is apparently "also known as carbon tetrabromide" and "both names are acceptable under IUPAC nomenclature, depending on whether it is considered as an organic or an inorganic compound". Categorised as both a halomethane and an organobromide, it is currently in a sub-category of organic compounds
• ICC also contains carbon tetrachloride (which the article states is an organic compound) and tetrafluoromethane and carbon tetraiodide, all of which are categorised as halomethanes and hence are sub-categories of organic compounds
• The cyanides category is a sub-category of ICC, and contains the article cyanopolyyne, an organic stub covering a class of compounds the simplest of which is cyanoacetylene, HCCCN, a clear organic compound. The cyanides category also includes dicyanoacetylene whose chemistry is noted for being a powerful dienophile in Diels-Alder reactions
• The oxocarbons category is a sub-category of ICC, and contains numerous examples of compounds that are plainly organic, such as benzoquinonetetracarboxylic dianhydride, deltic acid, hexahydroxybenzene trisoxalate, and rhodizonic acid - and these are just some examples.
  • Hey, wait a aminute -- deltic acid and rhodizonic acid are not oxocarbons. Their fully ionized anions are oxocarbon anions, but "deltate" and "deltic acid" are quite distinct chemical species.

Short version - there is a lot in the ICC category that is organic. EdChem (talk) 08:34, 30 January 2011 (UTC)

I would simply suggest to make the borderline compounds group in both organic and inorganic category.--Stone (talk) 09:20, 30 January 2011 (UTC)

It's so messy to do that though, considering how cluttered the organic and inorganic categories already are. To be honest, who actually looks through Category:Organic compounds to find what they want? No-one does, we all use search engines. I think these big categories are really to help us curators categorise the subcategories.

It might be nice to have an exhaustive list of borderline cases somewhere, though, for reference.

Ben (talk) 09:56, 30 January 2011 (UTC)

Assorted categories and stub templates to contain carbon containing compounds where no C-H moeities are present? --Plasmic Physics (talk) 10:11, 30 January 2011 (UTC)

Sorry Plasmic, I don't quite understand what your message above means, please elaborate.

Ben (talk) 10:50, 30 January 2011 (UTC)

Second possible condition:

If the compound contains a C-H, then the compound equals organic, else...

If the compound does not contain C, then the compound equals inorganic.

If the compound does not equal organic or inorganic, then the compound is ambiguous.

Create, categories and stub templates for ambiguous compounds as appropriate. --Plasmic Physics (talk) 11:02, 30 January 2011 (UTC)

By that definition, sodium carbonate is ambiguous as is calcium oxalate - both of these are conventionally considered inorganic. Organic compounds like benzenehexol, urea, chloroformic acid, trichloroacetic acid, and rhodizonic acid also all end up as ambiguous. I think this needs more work. EdChem (talk) 11:30, 30 January 2011 (UTC)

I think that an important source of confusion simply also arose from the effort to categorize the chemistry stub pages in inorganic or organic chemistry stubs. As well told hereabove by Jorge Stolfi there is the chemical compounds on one side and the chemists (or the chemistry culture) on the other side, with historical and cultural background differences between labs and teachers inherited from the way they have studied chemistry.
When a not yet well developed page (chemistry stub) dealing with an inorganic compound (e.g., silane, siloxane, triazene, …) which is the precursor (or wears the parent name) of an important class of organic substances (siloxane, triazene compounds, …) has a strong connotation of organic chemistry because of the language and the terms used in the text of the page, it is quite confusing for the reader to realize that this page is labeled as inorganic stub.
So, to summarize: we have to be prudent not to confuse chemical compounds and chemistry, or compounds category and stub page classification. Shinkolobwe (talk) 14:44, 30 January 2011 (UTC)

Sigh, Plasmic Physics, chemistry is not always black or white - sometimes it is grey. Some compounds have a significantly used systematic name, and there that systematic name can be reliably referenced, others names have to be 'synthesised'; some compounds are clearly organic, some are clearly inorganic. Others are a borderline - all the salts of organic acids are borderline. There is nothing wrong with adding both stub-templates (i.e., an {{organic-compound-stub}} and an {{inorganic-compound-stub}}) to it - just like some compounds are both a {{organic-compound-stub}} and a {{drug-stub}} (and I would not be surprised that there are compounds with 3-4 different stub marks on it). There is no need for overspecific categorisation of these things, there is no need to put everything exactly in the one single box where it fits perfectly (I would in some cases even find such too specific categorisation of stubs hampering progress of editing Wikipedia - Thiosalicylic acid is a perfect case of a {{organic-compound-stub}} - putting it into {{aromatic-stub}} misses the fact that it is also an {{organic-acid-stub}}, an {{acid-stub}}, a {{thiophenol-stub}}, a {{benzoic-acid-stub}} and a {{thiol-stub}} - which for some compounds (here already) starts to run out of hand, and hence {{organic-compound-stub}} is just enough! and now I know that you are going to suggest that {{aromatic-stub}} can go, since it is all covered by the others .. I don't even know why I started to respond to this thread - but to answer my own rhetoric question: there will be cases out there which would just fit '{{aromatic-stub}}' - so it is of use somewhere - just that some are too grey to get into there and are better left in a {{grey-stub}}). --Dirk Beetstra ^{T C} 17:19, 30 January 2011 (UTC)

Beetstra just summed up my opinions perfectly. The reality is, as implied by Smokefoot also, there is no precise border. Any attempt to define this will just create more problems than it solves. We should adopt our usual common sense approach and say, "let the editor decide". If it's blatantly wrong, let another editor fix it. That's the wiki way. Walkerma (talk) 17:35, 30 January 2011 (UTC)

I have already shown to be open to the idea of a grey area, we need to find a way to decide if an article is in the grey area or not. --Plasmic Physics (talk) 21:40, 30 January 2011 (UTC)

• But that is the point --- any clear-cut "official" definition will be (a) original research and (b) fundamentally irrational. Having three categories (org/inorg/grey) instead of two will only make the problem worse. The proposal is to let the gray area be fuzzily defined as "those articles where editors disagree", note that sibling categories (even organic/inorganic) are not mutually exclusive, and advise editors to be tolerant of dissenting opinions. All the best, --Jorge Stolfi (talk) 00:09, 31 January 2011 (UTC)

Exactly as Jorge Stolfi says. Plasmic Physics, your desires to 'find a way to decide if an article is in the grey area or not' and to 'define conditional rules' is NOT 'just leaving it in the grey area (or even wrongly in only black or only white) and move on', you want to 'define how much black and how much white there is in situation to get a specific shade of grey'. That type of thoughts are just the ones where all these editors here react against (and is the same type of remarks as in earlier cases), and I am afraid that this is a, yet another, case where your (well intended and good faith) edits or intended edits may annoy other editors around (as here, you move it from 'some general grey area' to 'one specific shade of grey area', I am sorry, the original grey area was better than the new one - accept that a too wide grey area is sometimes better than a specific grey area).

I hope, that you are not going to use the thoughts expressed in this thread to develop your own conclusion of what we say (as opposed to what we mean) and use that to perform edits and re-organisations and deletion suggestions! As I (and others as well have) said a couple of times, you do a lot of useful and good work, but please stop trying to put things into overspecific boxes - Note that a well intended bad edit is still a bad edit. And when there are too many well intended but still bad edits .. people will loose (and are losing) faith (and I am afraid that some editors, when they log in in the morning, first check all of your latest edits - which should be a total waste of time, which it unfortunately is not, and hence is disrupting their editing experience). --Dirk Beetstra ^{T C} 08:41, 31 January 2011 (UTC)

When is a too wide grey area better than a specific grey area? When is a box overspecific? --Plasmic Physics (talk) 09:49, 31 January 2011 (UTC)

QED. --Dirk Beetstra ^{T C} 12:46, 31 January 2011 (UTC)

Once again, you give an answer without an answer, as is your habit. --Plasmic Physics (talk) 04:47, 1 February 2011 (UTC)

Plasmic Physics, the answer is already given, your questions are just showing that you do not read the answers. --Dirk Beetstra ^{T C} 08:00, 1 February 2011 (UTC)

Science is not thinking in boxes! If you look at formic acid and you have an open mid you see the aldehyde group, you see the carboxylic acid group, you see that it the hydrate of CO and you know that this determines the molecule. If you think in boxes you simply say formic acid is the carboxylic acid with the smallest chain length and you loos all the other things. Sometimes science has to explicitly state that there is grey area and that categorezation is not possible. With stub categories it is the same a 100% definition of the boarders of the grey zone will not be possible and for every single compound there should be looked for consensus and discussion. --Stone (talk) 09:24, 1 February 2011 (UTC)

Yet, we make provision for said categorization? --Plasmic Physics (talk) 09:52, 1 February 2011 (UTC)

Yet another example of your black box/white box thinking, Plasmic Physics .. YES, some things fit perfectly in one box, sometimes it does not. Remember the categorisation-changes you tried to implement earlier, and where you were told that over-categorisation is not good. But still - diff, diff/diff and diff (as examples) .. but I already mentioned that you would do that earlier, did I not? --Dirk Beetstra ^{T C} 10:01, 1 February 2011 (UTC)

There is category of contributing users and the category of vandals. I think I will do a black and white categorization now.--Stone (talk) 16:02, 1 February 2011 (UTC)

Beestra: I was being WP:Bold, besides there is no way to have known that you see it as over-categorization. --Plasmic Physics (talk) 04:33, 2 February 2011 (UTC)

Stone: You're welcome to act five years old, but do not assume that I would responde with equal zeal or maturity. --Plasmic Physics (talk) 04:33, 2 February 2011 (UTC)

You act like a two year old! --Stone (talk) 07:46, 2 February 2011 (UTC)

Plasmic Physics. First, the name is Beetstra, please get it correct. Secondly, here I mention "There is no need for overspecific categorisation of these things, there is no need to put everything exactly in the one single box where it fits perfectly (I would in some cases even find such too specific categorisation of stubs hampering progress of editing Wikipedia)" and here "please stop trying to put things into overspecific boxes" - Nonetheless, you do that type of edits. And seen that the large majority of the editors here agrees that things should not be overcategorised, those edits are disruptive. Hence, it is not that only I see it as overcategorisation, all voices are that way (do others here have to say here explicitly that you are overcategorising as well, that you are putting everything into specific shades of grey, or that it is clear that you are trying to define every specific shade of grey. And it is fine that you are bold, but do not forget that WP:BRD exists (and while things are under discussion they should not be changed - which also goes for the case where the discussion does not get to a single solution - no consensus is also a form of consensus, in which case things simply don't change. Applying those (bold) changes while there is no consensus is however disruptive and likely a WP:POINT-violation. Especially since you were (09:41, 31 January 2011) asked to just leave it for the moment (still, shortly after that, diff - what, you are even edit warring over it [3] - [4] - [5] - [6]). WP:BOLD does not apply, the edits are just plainly disruptive (and I am sorry, the most of the examples I gave are also simply incorrectly categorised, I disagree with the stub-marking there). Actually, an admin should have plainly blocked you for 'Unexplained removal of stub templates after Jorgi Stolfi says 'no use caling it a stub (sic; emphasis added by me).

Maybe we all have to act here as five years old with you now, Plasmic Physics. Maybe that is the language that makes you understand. At the moment, I am categorising you in both a category of useful users ánd in a category of vandals. I could make that more specific categories, but I'd prefer that you see to it that you are removed from the latter category altogether. Hence, stop it. NOW. --Dirk Beetstra ^{T C} 08:22, 2 February 2011 (UTC)

And since you responded to my thread - here you knew for sure that maybe you should be careful with overspecification - and marking Muldamine as an ester-stub .. oh my .. what happened to amine, alcohol, &c. &c. Steroid-stub makes sense, but removing {{organic-chemistry-stub}} in favour of {{ester-stub}} - {{organic-compound-stub}} is really specific enough. --Dirk Beetstra ^{T C} 08:53, 2 February 2011 (UTC)

1. Three reverts is called edit waring, not two.
2. "No use calling it a stub" is not a sufficient explanation.
3. You refuse to specify what overspecific boxes entails, so for the sake of being bold, I am not liable for your discontent.
4. Overcategorization is a new topic, being informally discussed; applying changes whilst this new topic is being discussed is excluded from being a WP:Point violation.
5. I was not asked to stop for the moment, I was asked to stop overcategorizing, this is a meaningless request if overcategorizing is not defined. According to my logic, I am not - that is why you must define overcategorization.

--Plasmic Physics (talk) 09:20, 2 February 2011 (UTC)

You should read up on your definitions of edit warring, and how the three revert rule is part of that. Your word was 'unexplained', not 'insufficient explanation' - quite a differentce. And I think it was explained, putting something in an ester stub which is also an alcohol stub and a amine stub (and probably way more) is over-specification, that was explained, but you seem not to see that. We are clearly discussing stubs here, you even initiated the thread wanting to know how to do it, and while people are telling that you should see it broad, grey, and ask you not to do it too specific, you do it in a too specific/incomple way. People are saying, keep it broad. And yes, actually pushing it too specifics in mainspace where broad was applied, while you are the proponent of specifics, and everybody else is saying 'keep it broad', is a WP:POINT violation. And again, stop asking for black or white boxes, or even for what the specific grey of said box is - Putting Muldamine into a ester-stub-category is too specific, and that type of examples were given before. --Dirk Beetstra ^{T C} 09:52, 2 February 2011 (UTC)

The previous stub template examples you listed were nonexistant, your explanaition didn't make sense. I initiated the thread to find out how to decide between organic and inorganic or another stub template for chemical articles, not to decide between sub-stub templates. I am not pushing for anything, I am using sub templates that are availiable for use. I am not the proponent of specifics, I am the proponent of the most appropriate template. --Plasmic Physics (talk) 04:44, 3 February 2011 (UTC)

That is the point, Plasmic Physics, on a big steroid molecule with many functional groups, the ester is not the most important. You are right, we could create a massive number of stub-categories, and add them ALL to those big molecules, but that does not help, at all - those are simply just better in {{organic-compound-stub}}. Adding them to {{ester-stub}} (with AND without adding them to all the stub-categories for all possible functional groups) is totally useless - one would get on some probably 5-10 different categories. And then, why do the others not exist (by the way, {{amine-stub}} does exist .. but you did not bother to add that to Muldamine) - well, because for some of them you would get just one single compound in it every now and then. And digging through a tree of stubs is then not helpful. It is the same as with your overcategorisation - it does not make sense to make such specific groups when those groups are going to have just one or two in it. Then they are better one level higher, or even 2 levels higher. Here is yet another one. Why only alcohol stub? According to your reasoning, because {{diterpene-stub}}, {{ether-stub}}, {{cosmetic-stub}}, and maybe others, don't exist. If they would, you would add all, and if we say don't add it to {{alcohol-stub}}, then you ask why do we have {{alcohol-stub}}? And when we say that it is too specific for this compound, then you want rules when something is too specific and when not. Well - the story is the same as for the categorisations you did some time ago. --Dirk Beetstra ^{T C} 08:17, 3 February 2011 (UTC)

If they did exist then, rather than add a 101 stub templates, I would add organic-compound-stub, but since they don't, I wouldn't. I want rules because, you keep complaining. If there were rules, I would not have to be on the knife's edge constantly, concerned about your or other's possible complaints. --Plasmic Physics (talk) 08:43, 3 February 2011 (UTC)

'I want rules because you keep complaining' - no, it is simpler than what you say - 'You want rules' - full stop. Whatever, Plasmic Physics, don't worry, we will keep looking after your edits. --Dirk Beetstra ^{T C} 09:14, 3 February 2011 (UTC)

OK. We can define an organic compound as one that can participate as a reactant in organic reactions. This means that ammonium cyanate, even though it was rearranged to urea in the synthesis that started organic chemistry, is not an organic compound because that one involved a physical process, not a chemical one. However, things like chloroform are organic because this one can participate in free-radical halogenation, an organic reaction. Are you happy with this? FREYWA 04:18, 6 March 2011 (UTC)

Hi Freywa, thanks for your contribution, but I'm sorry to have to say that your 'solution' would not work, for several reasons. Firstly, it would lead to the misclassification of numerous compounds, including:

• a hydrohalogenation reaction, such as the one below, is clearly an organic reaction and from your definition it would follow that HBr must be an organic compound

• haogenation of an alcohol with PBr₃, shown below, would lead to the classification of phosphorus tribromide as an an organic compound

• the cyanohydrin reaction would also add several questionable compounds to the "organic compound" catgegory, including NaCN in the example below, and possibly H₂SO₄

Reaction of acetone with sodium cyanide to hydroxyacetonitrile

• electrophilic aromatic substitution would add several non-organic compounds to the organic list, such as bromine (with or without a Lewis acid, depending on whether the aromatic ring is activated) and nitric and sulfuric acids. The hydration of chlorobenzene (the Raschig-Hooker process for industrial production of phenol) would make water an organic compound, whilst the production of phenol from benzenesulfonic acid would make sodium hydroxide an organic compound.
• even CO₂ would be categorised as an organic compound on the basis of Grignard reagants such as the one between phenylmagnesium bromide and carbon dioxide to synthesise benzoic acid

Secondly, I think that "ammonium cyanate, even though it was rearranged to urea in the synthesis that started organic chemistry, is not an organic compound because that one involved a physical process, not a chemical one" is highly debatable. WP's article on this synthesis describes it as a chemical reaction, it satisfies the usual definition of producing a new chemical substance, and I am unaware of any physical process by which the synthesis can be reversed.

Thirdly, whilst I encourage your initiative in searching for a new approach, I'd encourage you to think carefully about whether a simple idea may have been considered before. Test an idea with the edge cases that cause problems for other definitions. With an area like the border of organic and inorganic chemistry, a lot of time has been spent in debates (including here) which suggests that simple solutions have been considered and discarded in the past.

Fourthly, even if you could find a suitable definition to avoid there being edge cases between inorganic and organic chemistry, WP policy would prevent its use until it found acceptance in reliable sources.

I don't mean to be harsh – I do encourage your trying to find a new approach – but your suggestion has some problems. Regards, EdChem (talk) 12:59, 6 March 2011 (UTC)

The worklist

To all those who are in this WikiProject: I have some urgent news for you.

The worklist is very out-of-date. Here are some reasons for you to get back into it:

• Edit history. The last edit was made like a year ago. In Wikipedia terms, that is real bad. Can somebody go there and improve the articles?

• Goals. Because of this neglectance to go improve the articles, the goals have not yet been reached. Which is very disturbing. The purpose of the WIkiProject will be defeated if nobody goes to edit those pages within a week. (OK, just joking.)

• The editors. Without work to do, the editors will be abandoning this WikiProject sooner or later. We need to get back in before these editors make up their minds for good and get out of here.

So, I hope you understand and make up your minds now. FREYWA 07:18, 27 February 2011 (UTC)

I really don't think the situation is as bad as you make out. We're probably so busy working on articles, we don't have time to update the worklist.

Relax. What's the worst that can happen?

Ben (talk) 19:19, 5 March 2011 (UTC)

Potash Pottasche

I know the German word Pottasche and it is only used for potassium carbonate. The mining products containing potassium like the chloride and sulfate of potassium are called Kalisalz. The Mineral Handbook USGS describes the change of the meaning from potash being only potassium carbonate to all potassium minerals in the 1950s. Now the page of potash links to the German article Kaliumcarbonate which is wrong. I will change that. One thing I wanted to know is if in chemistry this change of meaning also happened. Another point is: If I get a truckload of potash for fertilizer production could this also be potassium carbonate or is it only the sulfate and the chloride. If this is the case Pottasche and potash would have a minimal overlap.--Stone (talk) 20:04, 6 March 2011 (UTC) --Stone (talk) 20:15, 6 March 2011 (UTC)

More overspecialized categories

I have noticed that most of the subcategories in Category:Heterocyclic compounds (3 rings) have a very small number of articles in them (3 or less). These seem like overspecialized categories to me. If no one objects, I would like to empty many of them by moving the articles to more reasonable categories. Then I would like to tag them for deletion. Any comments? -- Ed (Edgar181) 20:08, 13 January 2011 (UTC)

Quite a few of the subcategories in Category:Heterocyclic compounds (2 rings) also have only one article in them. -- Ed (Edgar181) 20:11, 13 January 2011 (UTC)

I would also strongly argue the fact that do we need the "2 rings" / "3 rings" - as a lot of the compounds are not in the correct category - some users have counted the number of rings, some have counted only the number of rings with a hetero atom e.g in "2 rings" Asperlicin, Benzimidazoline, Ritanserin. It's a right mess. Let's drop the number of rings.  Ronhjones  ^(Talk) 23:23, 13 January 2011 (UTC)

In view of the recent problems with categorization, I would recommend that only certain editors be allowed to create categories. Say reviewers or rollbackers. I dont think that these standards would prove overly restrictive.--Smokefoot (talk) 23:43, 13 January 2011 (UTC)

Reviving this discussion....

Based on the discussion above, I have been trying to reduce the number of categories which contain very few (very often just one!) article. About 150 such subcategories of Category:Heterocyclic compounds have been emptied and deleted. There are still many dozens, perhaps hundreds, more. Most were created by User:حسن علي البط. I have asked this user on his talk page not to create any more of these categories without first getting input from this Wikiproject, but he has not replied. In fact, he has recreated some of the deleted categories, re-added some these useless categories to articles, and even started creating all new categories for single articles. Personally I find this behavior disruptive and contrary to consensus. Could I please have a little assistance dealing with this situation? I have invited حسن علي البط to contribute to this discussion here. -- Ed (Edgar181) 01:15, 19 February 2011 (UTC)

I also find the behavior disruptive since, to the extent that readers consult categories, they are less useful if they are too specialized. Other editors that have been doing this kind of work are User:Nono64 and User:Kupirijo. Nutty.--Smokefoot (talk) 16:20, 19 February 2011 (UTC)

Agree. We've been through this here before...while there was some support for recategorization work, there was not general support for being overly specific, and there was clear support for getting a plan together before individual editors each with their own ideas for the best terminology or level of detail going it alone. It's disruptive, and it consumes large amounts of time that could be spent actually fixing content. DMacks (talk) 16:46, 19 February 2011 (UTC)

Peace on who follows the right. I do apologize for not keeping in touch with writers on this page now but I was concentrating on my work and I did not know that many creative conversations are here. About the aspect of this conversation, I think that the chemical structure has huge importance in distinguishing between chemical compounds and explaining its pharmacological or toxicological effects and so the fact that many categories contain very few article (often one or two) does not explain cancelling them, as they will grow later because only very fiew of the professionals act on this point. In the future, we will need this categorization especially the "2 rings" / "3 rings" which I hope to develop them asap to contain subcategories as Category:Nitrogen heterocycles (2 rings) and Category:Oxygen heterocycles (3 rings) for example which will simplify the chemical structure for non professionals. This matter was a dream for me for a long time so please don not stop this work after all this effort. thanks alot.--حسن علي البط 00:17, 21 February 2011 (UTC)

I appreciate your willingness to contribute to chemistry articles here, but I think you need to realize that your "dream" for creating complex categorization does not have broad support among other chemists here. One of the core principles of Wikipedia is consensus, and I'm sorry, but there simply isn't consensus to support your effort at categorization. I think you should abide by the suggestion made on your talk page that you ask here first before creating any new categories, and only create them if there is consensus to do so. Thank you. ChemNerd (talk) 13:04, 21 February 2011 (UTC)

حسن علي البط continues to create new categories which apply to only small numbers of chemical compounds (Category:Pyranoindoles, for example). This is clearly against the consensus of other wikichemists expressed here and on his talk page. ChemNerd (talk) 13:56, 25 February 2011 (UTC)

I have undone some of their last work as far as I could easily do it. Sigh. This is tiresome, yet another re-categoriser who wants to push their scheme (the fun would start when the categorisation scheme pursued by this editor would conflict with the categorisation scheme another editor would want to implement .. categorisation-wars?). I have made my request on User:حسن علي البط's talkpage a final request to stop, to help undo the current actions, ánd to FIRST discuss. Time for more drastic measures? --Dirk Beetstra ^{T C} 14:29, 25 February 2011 (UTC)

The overspecializers have generally ignored pleas from the community of editors. So I hope that there is some mechanism to stop and undo the disruptive behavior by User:حسن علي البط (as well as by by User:Kupirijo). --Smokefoot (talk) 14:41, 25 February 2011 (UTC)

Back to categorization

Peace on who follows the right. Dear editrors, I noticed the creation of a new category Category:Nitrotoluenes created by a professional user User:Ronhjones. Tis category is considered a subcategory of my deleted one Category:Toluenes, so I request to reset this category to enable the right categorization. I donot agree with the editor who think that the category which apply to only small number of chemical compounds is against the policy of categorization, because even this category will be subcategorized later and will be needed. With my all respect,--حسن علي البط 06:42, 6 March 2011 (UTC)

Since Category:Nitrotoluenes has only a couple of articles in it, I think it would be better to move them all to Category:Nitrobenzenes and eliminate Category:Nitrotoluenes. Category:Toluenes would then be unnecessary, too. ChemNerd (talk) 17:54, 8 March 2011 (UTC)

Again ..Categories

Bringing this here again .. Today I noticed Plasmic Physics to change some Category:aldehydes to [[Category::carbaldehydes]] (where was this discussed anyway, why do we need to specify aldehydes further?). I noticed that as well on N-Formylpiperidine - which raised my eyebrows. That is NOT an aldehyde, a formamide at best ... Notably .. here is the edit that changed this compound from Category:Amides to Category:Aldehydes - totally wrong in my opinion, and today it was changed to the Carbaldehydes category.

Now, We've had numerous discussions about specialised categories, and there are many votes against it. Clearly, in my opinion, the editors that are pushing those categories show very little chemical sense, just applying their categories without even checking what it is about, and, really, calling N-Formylpiperidine an amide is more than specific enough.

I propose here, that we apply some community santion to these editors, disallowing them to do any form of category change without discussion per page. Any violation of these sanctions will result in an immediate block with increasing length. --Dirk Beetstra ^{T C} 12:38, 7 March 2011 (UTC)

I have undone the whole set of category changes that Plasmic Physics applied today, and deleted the categories. Plasmic Physics has been asked to first discuss the changes before applying them (with the note that if there is no consensus, or if no-one applies, that he should assume that there is no consensus, and hence, that the changes should not be applied). --Dirk Beetstra ^{T C} 13:10, 7 March 2011 (UTC)

For the record, of all the substances under Category:Aldehydes, there are at least 21 candidates for Category:Carbaldehydes. Plasmic Physics (talk) 13:15, 7 March 2011 (UTC)

Yes, but why? --Dirk Beetstra ^{T C} 13:24, 7 March 2011 (UTC)

Sorry, likely not clear enough. Why should we use the more specific category in stead of the general one? --Dirk Beetstra ^{T C} 13:25, 7 March 2011 (UTC)

Just out of curiosity, what criteria was used to distinguish an aldehyde from a carbaldehyde? ChemNerd (talk) 20:06, 7 March 2011 (UTC)

It's nothing special, it's just an aldehyde stuck on a ring. e.g. pyrrole-3-carbaldehyde = 3-formylpyrrole.  Ronhjones  ^(Talk) 21:39, 7 March 2011 (UTC)

ChemNerd: Carbaldehyde is a systematic suffix alternative to the formyl prefix, when the group is attatched to a cyclic group other than benzene.

The category of aldehydes encompases a varienty of substances too diverse to be of any particular use in finding related articles. Yes, their all aldehydes, but that does not make them all closely, chemically related. At the moment, is serves no other purpose as to simply list articles. Plasmic Physics (talk) 22:48, 7 March 2011 (UTC)

ChemNerd: Now you see why most editors are pleading that this re-categorizing business cease. My guess is that hardly anyone knows the difference between carbaldehyde and aldehyde (I don't), so and pity the average reader ... --Smokefoot (talk) 01:49, 8 March 2011 (UTC)

Ronhjones, I see how this compound can be classified as an aldehyde, but that is, FAR, besides the point.

The point is, there are editors that keep re-categorising articles, and, as ChemNerd curiously asks, disambiguous ways of classifying compounds. Yes, we are currently not doing it in a good and consistent way. And yes, we may need to come up with a better scheme. The trouble is, that there are now several people who are busy with categorisation schemes which are not documented, based on 'yes, they are all aldehydes, but some are carbaldehydes', 'all aldehydes are now in one category, and it does not help to find articles'. That is all fine, Plasmic Physics, and others who are are doing massive category changes, but you and others have been asked to first come up with a scheme, discuss that scheme and get to a consensus, and then apply that systematically. Now there are 4 editors doing those scheme changes, all using their own criteria, some are pretty vague ('Yes, they are all aldehydes, but that does not make them all closely, chemically related' - does splitting of the carbaldehydes group compounds that are chemically related, I don't think that N-formyl-piperidine is reacting as a carbaldehyde, surely it reacts more as an amide, or formamide), do we want to categorise articles

• by chemical reactivity-relation - how does one aldehyde react as the other one .. maybe there is a more reactive functional group in there that reacts first, or whatever.
• according to (all!) possible functional groups - and then, is it amides, or formamides, acetamides, cyclic amides, dialkyl amides, monoalkyl amides, monoalkyl formamides, other amides, whatever
• broadly, so just NOT overcategorise, and group them only in 4-5 main functional groups - i.e., amides in amides and not in the specific ones

Plasmic Physics says it is a POV that I find their (and others) work overcategorisation, still, we have different POVs here, in other words, we do NOT have a consensus on what schemes to follow. I am sorry, that has been clear now for months, people are complaining about the mistakes and the sometimes absurdly small categories that we end up with, which means, that maybe that is not the way forward. I and others have asked others to stop and to come up with a scheme first and discuss it, but no, no-one sets up a sub-page for it somewhere, they just continue with their own work, their own undisclosed schemes, and it is just a matter of time and we are going to be back here. Asking to stop did not help, so how do we go on? --Dirk Beetstra ^{T C} 09:32, 8 March 2011 (UTC)

I propose this: no-one recategorise anything without permission from here. All violations result in an automatic, lifetime ban from Wikipedia. And possibly planet earth.

Ben (talk) 12:17, 8 March 2011 (UTC)

I second the gist of Ben's suggestion - no categorization unless consensus is achieved. Our administrators should finally act by figuring out a mechanism to enforce this guideline. --Smokefoot (talk) 13:33, 8 March 2011 (UTC)

Citation templates now support more identifiers

Recent changes were made to citations templates (such as {{citation}}, {{cite journal}}, {{cite web}}...). In addition to what was previously supported (bibcode, doi, jstor, isbn, ...), templates now support arXiv, ASIN, JFM, LCCN, MR, OL, OSTI, RFC, SSRN and Zbl. Before, you needed to place |id={{arxiv|0123.4567}} (or worse |url=http://arxiv.org/abs/0123.4567), now you can simply use |arxiv=0123.4567, likewise for |id={{JSTOR|0123456789}} and |url=http://www.jstor.org/stable/0123456789 → |jstor=0123456789.

The full list of supported identifiers is given here (with dummy values):

• {{cite journal |author=John Smith |year=2000 |title=How to Put Things into Other Things |journal=Journal of Foobar |volume=1 |issue=2 |pages=3–4 |arxiv=0123456789 |asin=0123456789 |bibcode=0123456789 |doi=0123456789 |jfm=0123456789 |jstor=0123456789 |lccn=0123456789 |isbn=0123456789 |issn=0123456789 |mr=0123456789 |oclc=0123456789 |ol=0123456789 |osti=0123456789 |rfc=0123456789 |pmc=0123456789 |pmid=0123456789 |ssrn=0123456789 |zbl=0123456789 |id={{para|id|____}} }}

Obviously not all citations needs all parameters, but this streamlines the most popular ones and gives both better metadata and better appearances when printed. Headbomb {talk / contribs / physics / books} 02:35, 8 March 2011 (UTC)

Ambiguous units ppm, ppb, and ppt

I propose to get rid of the old and ambiguous units ppm, ppb, and ppt. The Wikipedia:Manual of Style (dates and numbers) says: "Only in the rarest of instances should ambiguous units be used, such as in direct quotations". I can see at least 3 ambiguities with these old units:

• The old units may either refer to mass fraction or mole fraction, which are quite different.
• The "b" in "ppb" stands for billion, which can either be 1E9 or 1E12, see Long and short scales.
• "ppt" is even worse: if may either refer to parts per trillion (1E-12) or to parts per thousand (1E-3).

Consistent with IUPAC recommendations (see IUPAC Green Book http://old.iupac.org/publications/books/gbook/green_book_2ed.pdf and also page 1387-1388 of http://www.iupac.org/publications/pac/67/8/1377/pdf), I suggest to make the following replacements:

old unit	ppt	ppm	ppb	ppt
definition	1E-3	1E-6	1E-9	1E-12
new unit (if mass fraction)	g/kg	mg/kg	μg/kg	ng/kg
new unit (if mole fraction)	mmol/mol	μmol/mol	nmol/mol	pmol/mol

A counter-argument that has been brought up is that the old, ambiguous units are still often used. In my research area (atmospheric chemistry), publications currently have a mix of the old and the new units. Although the old units still occur more often, there is a trend to the new notation. Thus, I think both would be consistent with WP:MOS which says: "In scientific articles, use the units employed in the current scientific literature on that topic. This will usually be SI, but not always". RolfSander (talk) 18:12, 5 March 2011 (UTC)

Good idea to raise this point, but my experience is that sometimes (or often, in fact) IUPAC's recommendations are unhelpful. WP:Chem is still dealing with IUPAC-jihadists who seem to prefer rules to readability/accessibility. In atmospheric chem apparently things are shifting, but in more mainstream chemistry, readers want to see units they are familiar with, despite minor issues with ambiguity. The links provide definitions. At least those are my views.--Smokefoot (talk) 20:57, 5 March 2011 (UTC)

"Old" units vastly dominate "new" units in non-chemical materials science literature. This partly hits the crossing point of chemistry and materials science (for which we have no project on WP). Any article, say on inorganic compound, is currently dealt with by WP:Chemicals, but chemistry is only a part of it reflected in the "Chemical properties" and "Preparation" sections. I don't think we should hit non-chemists editing those articles. Materialscientist (talk) 22:51, 5 March 2011 (UTC)

@Smokefoot:

"minor issues with ambiguity"

I would not call this "minor". For example, the conversion factor between a mass fraction of 1 ppb and a mole fraction of 1 ppb is 4.7 for the greenhouse gas CFC-11.

"The links provide definitions."

They don't. If they would, I wouldn't complain. Links usually go to the parts per notation page which still doesn't tell you if ppb refers to mass fraction or mole fraction.

@Materialscientist:

"I don't think we should hit non-chemists editing those articles"

I think especially the non-chemists need unambigous units. Inside a small research community, colleagues will probably know what you mean by ppb. Outsiders like non-chemists deserve an unambigous notation that does not require insider knowledge. RolfSander (talk) 23:47, 5 March 2011 (UTC)

Most non-chemists don't understand mole (maybe because it involves mass conversion which they don't know by heart); mg/kg is Ok with me, and I use it on WP because it is clear to everyone, but this works only for mass fraction. Surely mol/mol cancels conversion, but mol is still an odd unit to many. Materialscientist (talk) 00:03, 6 March 2011 (UTC)

That's exactly my point. If a non-chemist interprets "ppm" as "mg/kg", he/she has already been mislead by the wikipedia article if it was meant to refer to mole fraction (which is common in atmospheric chemistry). Regarding the odd unit "mol/mol", you can also define the mole fraction as "(number of molecules x)/(total number of molecules)" if that is easier. The first occurence of the new units should certainly be a link to its definition. RolfSander (talk) 00:24, 6 March 2011 (UTC)

I think that the current system is familiar to readers. Only a tiny fraction of readers actually do anything with ppm or ppb, they are mainly just comparing numbers. Anyone actually doing something with these numbers would need to examine the definition of the units, no matter what we decide. Imperfect, but I recommend that we err on the side of familiar even at the cost of ambiguity. --Smokefoot (talk) 00:33, 6 March 2011 (UTC) I should add, that the matter is not a big deal to me, so I will not object to emerging consensus.--Smokefoot (talk) 00:34, 6 March 2011 (UTC)

Not that it matters, but I vote for RolfSander's proposition. Plasmic Physics (talk) 02:37, 6 March 2011 (UTC)

Just a remark: the hereabove mentioned table might even contain a more important lacune: % (per cent). In fact when one provides a fraction, it is always a good practice to define the terms above and below the fraction bar. For mass fraction, wt. % is often used while for mole fraction mol % is used. Another lacune also deals with the volume fraction often used for gases: e.g., ppm Vol. However, if the context of the measurements is clearly given by the authors, the experienced reader should not be confused. In fact, if a reader hesitates, he/she is already on the good way to solve the problem by him/herself. And by the way, it is the first time I see someone using ppt for part-per-thousand in place of part-per-trillion. So, many depends on your previous experiences and maybe also on your mother language if you are not a native English speaker (sometimes an advantage in such matters). Shinkolobwe (talk) 23:03, 6 March 2011 (UTC)

Some replies: 1) Yes, the "%" is indeed another problem. Either writing "wt%"/"mol%" or adding "mass fraction"/"mole fraction" will remove the ambiguity. 2) Volume fraction is only useful for ideal gases, and then it is equal to mole fraction. 3) I agree that if the context of the measurements is clearly given by the authors, the experienced reader will not be confused. Unfortunately, however, the context is often not given. Also, I think we should remove ambiguities for the benefit of the non-expert. 4) ppt for 1E-3 is indeed rare but it exists, see e.g. http://acronyms.thefreedictionary.com/ppt http://answers.yahoo.com/question/index?qid=20100309074959AAhFpYO http://classes.mhcc.edu/web/ch222_mr/pdfLabs222/PartsPerThousand.pdf http://www.chembuddy.com/?left=concentration&right=ppm-ppb-ppt RolfSander (talk) 23:46, 6 March 2011 (UTC)

break

At RolfSander's request, I am copying this from Talk:Greenhouse_gas#Terminology

There is a current disagreement on terminology.

• ppm vs ppmv vs μmol/mol
• concentration vs mixing ratio vs mole fraction

In SI units, μmol/mol and mole fraction are the "correct" terminology. However, ppm is used in the IPCC documents and almost all the references.

The IPCC uses many phrases like

models project atmospheric CO2 concentrations of 540 to 970 ppm - (From WG1, page 22)

At first glance, the phrase "concentration of xx ppm" is technically wrong since "concentration" represents moles per liter. However, since the number of moles in a volume is known, "concentration" can also be interpreted as "fractions of a mole per mole" (depending on the units) which is what 540 ppm means. The titles of many of the references also use the term "concentration" with this meaning. In some references, the proper phrase is "a mixing ratio of xx ppm", though "mole fraction" is also correct. Many times, AR3 uses the term "abundance", as in phrases like "with abundances reaching 2,970 to 3,730 ppb".

From the IPCC TAR Glossary

Mixing ratio

See: Mole fraction.

Mole fraction

Mole fraction, or mixing ratio, is the ratio of the number of moles of a constituent in a given volume to the total number of moles of all constituents in that volume. It is usually reported for dry air. Typical values for long-lived greenhouse gases are in the order of mmol/mol (parts per million: ppm), nmol/mol (parts per billion: ppb), and fmol/mol (parts per trillion: ppt). Mole fraction differs from volume mixing ratio, often expressed in ppmv etc., by the corrections for non-ideality of gases. This correction is significant relative to measurement precision for many greenhouse gases. (Source: Schwartz and Warneck, 1995).

In AR3, the phrase "mole fraction" is not used very often. The following is from the caption of figure 11, page 44.

Change in CH4 abundance (mole fraction, in ppb = 10−9)

The uses of multiple phrases for the same concept indicates to me that the information is pulled from many sources and/or written by different people who use different nomenclature. At any rate, it is my opinion that changing this document to use non-standard nomenclature, even if it is "more correct", is a disservice to the readers. Q Science (talk) 07:49, 10 March 2011 (UTC)

Clarification: In the tables above, the "old unit" was NEVER the ambiguous term "ppm", it was "a mixing ratio of xx ppm" which is a well defined phrase. Q Science (talk) 07:57, 10 March 2011 (UTC)

Sorry to contradict but "a mixing ratio of xx ppm" IS ambiguous! It could either be "a molar mixing ratio of 1E-6 mol/mol" or "a mass mixing ratio of 1E-6 kg/kg". The former is usually used in atmospheric chemistry, the latter is usually used for toxic components in aqueous solutions. RolfSander (talk) 15:23, 10 March 2011 (UTC)

On the Keeling curve, the Scripps Institution of Oceanography reports the CO2 concentration in ppm. In the data (but not the text), it says "CO2 concentrations in micro-mol CO2 per mole (ppm), reported on the 2008A SIO manometric mole fraction scale. This is the standard version of the data most often sought."

As a result, ppm is the standard way all atmospheric gas concentrations are reported. IMHO, any attempt to change to another "standard" is just minor players trying to control the world class research centers. Q Science (talk) 21:31, 11 March 2011 (UTC)

Since you posted the same comment here as on Talk:Parts-per_notation, I post the same reply here: 1) Was it your intention to call me a "minor player"? Are you maybe overreacting because those "climate sceptics" drive you crazy? 2) I don't deny that many scientists from world class research centers report "concentrations in ppm". That doesn't change the fact that it is wrong. Try this: Make two plots of vertical ozone profiles. One showing concentration (1/cm3), one showing mole fraction (ppb). Do you see the difference? RolfSander (talk) 23:06, 11 March 2011 (UTC)

Aldehydes

I propose the following cattree, primary categories on the left:

- Acetaldehydes (7 candidates)
|
- Alkanals (21 candidates)
|
- Alkenals (7 candidates)       - Alkylalkenals (5 candidates)
                                |
                                - Phenylalkenals (5 candidates)
|
- Phenolic aldehydes (remove)
| 
- Benzaldehydes (7 candidates)  - Alkoxybenzaldehydes (9 candidates)
                                |
                                - Hydroxybenzaldehydes (10 candidates)
|
- Carbaldehydes (13 candidates) - Cycloalkene carbaldehydes (5 candidates)

Plasmic Physics (talk) 22:53, 8 March 2011 (UTC)

Why are any subcategories needed? 71.185.49.174 (talk) 23:45, 8 March 2011 (UTC)

They are the main contributors to the primary cats. Plasmic Physics (talk) 00:11, 9 March 2011 (UTC)

Are you asking about the primary cats or the secondary cats? Plasmic Physics (talk) 00:17, 9 March 2011 (UTC)

The problem with excessive subdivison is that you end up with more problem cases - in the above you separate benzaldehydes from carbaldehydes, when in reality benzaldehyde is just another carbaldehyde. That then gets you into difficulties with something like benzene-1,3-dicarbaldehyde aka 3-formylbenzaldehyde (names taken from an entry in Beilstein) - is it a benzaldehyde or a carbaldehyde, the whole thing makes it confusing for any casual reader.  Ronhjones  ^(Talk) 00:47, 9 March 2011 (UTC)

I would categorise it under carbaldehydes, alternatively, instead of creating a primary carbaldehyde cat, make cycloalkene carbaldehydes a secondary cat under benzaldehydes. Plasmic Physics (talk) 00:57, 9 March 2011 (UTC)

Benzaldehydes is a special case, that's why it is a stand alone category, smiliar to acetaldehydes and alkanals. Plasmic Physics (talk) 01:23, 9 March 2011 (UTC)

Why not use just Category:aldehydes without creating all these subdivisions? The aldehydes are grouped because they have similar properties in terms of chemical reactivity. When you create a bunch of subcategories, you've now separated like compounds into separate groups that are different only by some small semantic alteration. Phenylalkenals only differ from alkylalkenals in a trivial way that is unrelated to their properties as aldehydes. And similarly carbaldehydes also only differ from cycloalkene carbaldehydes in a way that is unrelated to their chemical properties as aldehydes. So why are any of the subcategories necessary, or even helpful? They seem completely counterproductive to me. 71.185.49.174 (talk) 01:53, 9 March 2011 (UTC)

Semantics? Really? Phenylalkenals are generally more reactive than alkylalkenals, they may participate in certain chemical reactions that alkylalkenals are excluded from. The aldehyde group is usually more acidic than alkylalkenals, phenylalkenals are more often carcinogenic. The aldehyde category as it currently stands, does not aid in locating articles that are reasonably well associated through their chemical properties, and only serves as a global list. Plasmic Physics (talk) 02:57, 9 March 2011 (UTC)

I don't think it is true that phenylalkenals are generally more reactive than alkylalkenals. In fact, if there is any notable difference between the two, it is that alkylalkenals are generally more reactive than phenylalkenals because the additional conjugation marginally stabilizes phenylalkenals. In any case, the difference between the two is more a matter of semantics than actual chemistry. 71.185.49.174 (talk) 12:32, 9 March 2011 (UTC)

I am indeed mainly with Ronhjones here, and with 71.185.49.174. You get into problems, and really, carbaldehydes (note, we don't even have the article) and aldehydes are not significantly different, and the difference is going to confuse readers. Reactivity is a bad way of splitting them, although alkyl aldehydes show a different reactivity then e.g. benzaldehydes, there are some benzaldehydes which are difficult to turn into Schiff bases, and there will be also alkyl aldehydes which are pretty unreactive. If any, the tree could be:

Category:Aldehydes
|
- Category:Benzaldehydes (where the aldehyde group is on an aromatic group)
|
- Category:Aliphatic aldehydes (where the aldehyde group is connected to an sp3-type carbon
|
- Category:Aldoses (for the 'aldehyde-sugars')

Note, I agree, the recently created Category:Phenolic aldehydes should be depopulated, maybe into a Category:Benzaldehydes category - that is just the thing I mean with overcategorisation - what is next, Category:Phenolic toluene aldehydes, Category:Brominated phenolic toluene aldehydes. That is just the thing that pushes it too far. If there are not too many functional groups, they go into both Category:Phenols ánd Category:Benzaldehydes, if there are too many functional groups, they should go into e.g. Category:Aromatic compounds (although I would not have a huge problem with putting them in a large set of categories for all general functional groups they have).

Splitting up the category tree too far is NOT helping the reader. Readers will look at a compound, think 'that is an alcohol' - so Category:Alcohol, they don't see it in the main category, but notice 'Category:Phenols' - that is closer so they go there .. and the compound should be there. They do not go to Category:Phenols to go to Category:Phenolic toluenes/Category:Phenolic aldehydes to go to Category:Phenolic toluene aldehydes/Category:Brominated phenolic aldehydes/Category:Brominated toluene aldehydes/Category:Brominated phenolic toluenes/... to get finally to their compound in Category:Brominated phenolic toluene aldehydes (hey, and now I only have 4 functional groups, there are some pretty exotic molecules out here on Wikipedia which also contain amide, ether and other halogens). Do apply KISS to this, please. And note, most readers will not even go through a category tree already, as it is too complex.

And based on that, Category:Aldehydes is significant, but it does not, yet, warrant a full splitting into too much (it is still just one page in the category). Categorisation is not a means to have everything correct, it is, still (though a lot of people hardly use it), just a way to be able to find articles relatively quickly. Note that we also don't have Category:Nobel prize winners that were born a Russian, from German descendance, now carrying a Dutch passport and working in the United Kingdom. Such are categorised as Category:Nobel prize winners Category:Nobel laureates in Physics, Category:Dutch people of Russian descent, .. the cross-categorisation does the trick, and when you do need to find your compound which is an aldehyde and a phenol, you go here. --Dirk Beetstra ^{T C} 08:15, 9 March 2011 (UTC)

OK, what if we focus on the most important primary cats first and ignore my secondaries.

- Category:Acetaldehydes
|
- Category:Alkanals
|
- Category:Alkenals
|
- Category:Benzaldehydes

Plasmic Physics (talk) 08:35, 9 March 2011 (UTC)

I'd suggest to, for now, combine Acetaldehydes and Alkanals (strange name, the latter) .. after all, propionaldehyde is just methylacetaldehyde. --Dirk Beetstra ^{T C} 08:48, 9 March 2011 (UTC)

When I first suggested the cattree, I designed it according to structural, not chemical similiarity. It only appeared that way for I had to explain the chemical difference after the IP enquired.

I can combine the suggested categories, but I need to mention that the reason for the Acetaldehydes cat, is that it is a special case as acetaldehyde derivatives are important and well known within the class of aldehydes.

Does that mean, the last three cats are supported? Plasmic Physics (talk) 09:25, 9 March 2011 (UTC)

Structural is also quite difficult .. their main structural comparison is that they are all aldehydes. That cat may grow a bit big, so a bit of splitting is maybe necessary .. Note that when newly created subcategories grow big that they might be split, either horizontally (e.g. from the Alkanals split of a group Acetaldehydes which becomes a subcat of Aldehydes) or vertically (just make a cat Acetaldehydes which is a subcat of Alkanals ..) ..

Lets wait until we get some more input from others. We might now do this for aldehydes, but what if this is not compatible with e.g. amines .. this needs to be seen in the wider picture. Note that other categories may need to be re-evaluated on a similar basis. But we don't have a deadline, do we? And there is a lot of other work to be done, anyway. --Dirk Beetstra ^{T C} 10:14, 9 March 2011 (UTC)

I'll construct a hypothetical model of primary subcats for amines. Plasmic Physics (talk) 11:48, 9 March 2011 (UTC)

Category:Aldehydes isn't especially overpopulated. The simplest way I can think of for making it a bit smaller is to put all the aryl aldehydes into a subcategory. Call it Category:Aryl aldehydes or something similar. Based on a quick glance, about half of the molecules in Category:Aldehydes contain an aromatic ring directly attached to a formyl group, i.e. ArCHO.

Category:Benzaldehydes is a narrower category than Category:Aryl aldehydes, because the former excludes non-benzene aryl groups, such as the furan ring in furfural.

One further subcategory that could stay is Category:Aldoses, because it groups together sugar aldehydes that are all more similar to each other than they are to the rest of the aldehydes. This category also separates aldehydes of central importance to biology from the rest.

Ben (talk) 11:52, 9 March 2011 (UTC)

If Category:Aldehydes is going to be subdivided, which I'm not sure is necessary, there really shouldn't be anything more than Category:Conjugated aldehydes (or some equivalent), Category:Unconjugated, and Category:Aldoses. I don't agree that acetaldehydes are in any way a special case of aldehyde that requires separate classification, or that benzaldehyes are that much different than other aryl aldehydes. 71.185.49.174 (talk) 12:32, 9 March 2011 (UTC)

OK, I see that there even a minimal subdivision of the aldehydes, as I suggested (with already there 'if any, the tree could be'), nor as others have suggested, does not seem to gain any traction, the editors generally think it is just not necessary. I think we should just not split up the aldehydes. I will also de-populate the 'phenolic aldehydes' (which I think is way too specific). --Dirk Beetstra ^{T C} 13:26, 9 March 2011 (UTC)

Thank you!! Perhaps we can all agree to stop creating categories and get back to our main focus, content.--Smokefoot (talk) 13:39, 9 March 2011 (UTC)

I had a go at "categorising" our aldehyde articles: User:Benjah-bmm27/aldehydes. I do not suggest we actually apply this scheme. It might be useful for making a template for the n-alkyl aldehydes, or something similar. But it was really just for me to get my head round the similarities and differences between the aldehydes we have articles on. A tribute to procrastination and the Victorian obsession with classification

Ben (talk) 18:10, 12 March 2011 (UTC)

I have a similiar article: User:Plasmic Physics/Aldehydes. Plasmic Physics (talk) 00:22, 14 March 2011 (UTC)

FfD: ball-and-stick models without hydrogens

Notice: I nominated a few ball-and-stick models without hydrogens for deletion: Wikipedia:Files for deletion/2011 March 14 --Leyo 00:32, 15 March 2011 (UTC)

I won't disagree with deleting those you nominated, but excluding hydrogens is quite acceptable in some contexts. Even excluding entire fragments. Of course, this is usually stated explicitly. --Rifleman 82 (talk) 03:18, 15 March 2011 (UTC)

I think these images suffer from many more problems than just omitting hydrogens. They rotate (lame) and are all pixelly (double lame).

All round lameness. Nuke 'em.

Ben (talk) 19:13, 15 March 2011 (UTC)

There are even more such images on User:Bryn C/Contributions/Images/Organic chemistry/Alcohols. If the result will be deleted, we might nominate a second batch. --Leyo 22:27, 15 March 2011 (UTC)

Reactivity of zirconium with water steam at high temperature: hydrogen production in Fukushima reactors

The tragedy of Fukushima and the explosion of hydrogen gas above the containment buildings of nuclear reactors pose the delicate question of the reactivity of zirconium and zirconium alloys with water steam at high temperature in a damaged nuclear reactor core. The page about zircaloy should deserve a special attention and the contribution of critical reviewers. See also the talk page for questions and useful references: Talk:Zirconium alloy. Any help would be appreciated. Shinkolobwe (talk) 14:05, 20 March 2011 (UTC)

To skeletal or not to skeletal?

I recently saw this comment at Talk:Pentaerythritol tetranitrate.

Do we generally aim to include explicit (non-skeletal) formulas in articles that many non-chemists are likely to read?

I think it's probably a good aim unless the explicit formula would be so crowded it's illegible/confusing.

Ben (talk) 10:28, 16 March 2011 (UTC)

I replied there. Showing all carbons incl. attached hydrogens only makes sense in small molecules such as formaldehyde or isopropyl alcohol. --Leyo 10:39, 16 March 2011 (UTC)

I agree with Leyo. Explicitly showing all carbons and hydrogens is not very helpful for anything larger than a few carbons. -- Ed (Edgar181) 13:03, 16 March 2011 (UTC)

See, I think this is actually something of a failure of WP:CHEM. It's condescending to assume all readers who don't understand skeletal formulas don't understand structural formulas. Anyone who's studied chemistry to GCSE level in the UK should understand structural formulas, but unless they've done A-level chemistry, they won't understand skeletal formulas.

I propose adding one of the following images to the article Pentaerythritol tetranitrate:

• 
• 

Ben (talk) 15:48, 16 March 2011 (UTC)

Personally, I think it will be a rare occasion that someone will get useful information from one of these images but not from File:PETN.svg. But I don't have a strong objection to adding one of these two to the chembox. I would prefer File:PETN-semistructural-formula-2D.png. Going further, wouldn't it be better to add instead one of your nice ball-and-stick diagrams, Ben? This would convey all the information that is present in these two images, still be understandable to a more "novice" reader, and also provide some idea of three dimensional shape. PETN is not swastika-shaped, afterall.  :) In general, I think multiple representations are a good thing (the chembox at acetic acid is a good example). -- Ed (Edgar181) 16:02, 16 March 2011 (UTC)

(ec x 2)I would really use this with common sense. Where it is reasonably possible (like here), do include all hydrogens. If it for a molecule starts to obscure or they are impossible to place, then switch to a skeletal formula (omit all hydrogens except those which are structurally important). For the example here, as Ben shows, it is quite possible to add the hydrogens, I can imagine that for some steroids it is going to be undoable to reasonably show all of them.

Don't expect our readers to 'understand' or 'not to understand anyway', try to be complete - if they do not understand the complete picture, then that is as far as you could take them, but if they do not understand the skeletal formula while one could easily have provided a complete picture which they may understand (and more will understand the complete picture), then please, do so. Same would go for writing "CH₃COOH" vs. C₂H₄O₂ in prose. --Dirk Beetstra ^{T C} 16:06, 16 March 2011 (UTC)

But we don't want to focus too much on “dummies”, either.

Honestly, I don't like the two structures shown above. For example, a reader could misinterpret C–C–O as rectangular. --Leyo 16:56, 16 March 2011 (UTC)

Dirk: I have the same opinion as you. I'm not advocating such images for every molecule we have an article on, just for ones that (i) are of significant interest to non-chemists and (ii) are perfectly possible to draw neatly with explicit hydrogens.

Ed: The above structures are based on the crystal structure of PETN, looking down the S₄ axis. From this angle, it pretty much IS swastika shaped! It's the highest symmetry view of the molecule. I'm about to upload a 3D picture, I just had to wait to get home to my PC to make it. This is one of the main reasons I make so many 3D models - I think they're accessible to almost anyone who knows what a molecule is. The same cannot be said for skeletal formulae.

Leyo: I think misleading a reader as to the exact C-C-O angle is much less likely and much less of a concern than excluding them by refusing to describe the connectivity of the molecule in a language they can understand. Bond angles are a subtlety, connectivity is generally the most important aspect of molecular structure. Your comment that some of our readers are "dummies" alarms me – do you really think we should make Wikipedia an elitist place where the articles are impenetrable unless you're already trained in the field? We can make pentaerythritol tetranitrate easier to understand, without damaging it, so we should.

New images: a less swastika-y semistructural formula and a ball-and-stick model:

• 
• 

Jmol models of the PETN molecule and crystal packing for you to examine yourself. See if you can find a good orientation without atoms clashing - not easy! http://www.benjamin-mills.com/chemistry/structures/PETN/

Ben (talk) 19:50, 16 March 2011 (UTC)

I like File:PETN-from-xtal-2006-CM-3D-balls.png, so I have added it to the article. -- Ed (Edgar181) 13:58, 17 March 2011 (UTC)

+1 for that, Ed. Visibly includes all the atoms and connectivity, and also some 3D perspective that it's not flat or square. Thanks also (in general, Ben, and to others that do this...I just happened to remember to say it here!) for using an actual published structural geometry and citing it, rather than the apparent "I drew it and the program rendered it 3D" (with sometimes hilariously impossible conformations) that I find sometimes. DMacks (talk) 16:41, 17 March 2011 (UTC)

@Ben: Please notice the quotation marks and remember the fact that English is not my native language (i.e. I did not find a more appropriate expression). If we can make an article easier to understand without making it looking weird people with chemical knowledge, we should. File:PETN-from-xtal-2006-CM-3D-balls.png is a perfect add-on. However, I would not like depictions that would never be in a chemistry/science textbook to be added. Below some ideas to facilitate the understanding of chemical structures:

1. Adding the type of the structure (e.g. skeletal, ball-and-stick, space filling) incl. link to the article below each image in the chembox.

2. Adding a single link to the image section in the box that explains the various types of chemical formulas.

3. Adding an external link to a website where the substance is visualized in various types of chemical formulas based on e.g. SMILES.

--Leyo 16:38, 17 March 2011 (UTC)

I statically numbered Leyo's formerly bulleted list so the points can be referred to easily in discussion.

For idea 1, I generally dislike cluttering up the infoboxes more than they already are, and a line of text for each image (especially if we add several different ones (skeletal, explicit-atom-labels, 3D-balls, etc.) risks getting unweildy. A simple word ("skeletal") rather than a normal image-caption ("skeletal diagram of...") would be the most I could support. It's the minimum sufficient to explain it in a way that anyone who does care can actually learn about it. I like idea 2 in theory, but I am having trouble figuring out what to say that would help a reader who doesn't already know about structure-diagrams know where to look to learn about which diagram (unless they are each already labeled with the type, in which case we're back to idea 1). But also, whatever happened to "readers click on terms or other items of interest that they do not understand to go to a page with details explaining it"? The image explains something about the topic of the article, and other info (formula, other types of renderings, name) provide details to help interpret any one image in the context of that topic. Additional details about the image are not related to the topic of the image, so put them in a page about the image, which leads to another idea:

4. Make sure each image description page clearly states the type and links to an article about interpreting that type.

DMacks (talk) 16:57, 17 March 2011 (UTC)

Actually, this was a topic I had planned to raise here - if I was more on the ball I would have responded sooner! I'm a strong believer that purely skeletal structures are difficult for many of our readers to follow. We are all chemists, so the structures are clear to us - but many of our readers are students. Someone who needs to look up the structure of methanol or ethanethiol probably doesn't understand skeletal formulae. Also, a survey was done of UK chem teachers for the chem. ed. website I'm working on for RSC, and I was told that one of the strongest concerns was about skeletal structures that high school students struggle with. I'm not opposed to skeletal formulae at all - I've posted many myself - but for simple common (both!) things I think the first choice should be one with the hydrogens shown. We just need to define "simple" and common"! Compare Pentafluoroethyl iodide with Pentafluoroethane, and ask a high school student to explain each! Some good models to emulate are: Cyclopropane, 1,1-Difluoroethane. Walkerma (talk) 16:45, 17 March 2011 (UTC)

My view is very similar to yours, Walkerma. I'm going to update my image description pages so they have a link to the Wikipedia article explaining how to interpret them. See, for example, File:Serotonin-2D-skeletal.png. What about a question mark in each chembox that links to information on structural images, similar to the one at Japanese language? Where feasible, we should have skeletal and explicit structural formulas side by side. The skeletal formula satisfies trained chemists, the explicit formula satisfies those who've never seen a skeletal formula, and having both together satisfies those who are learning (or still mastering their understanding of) skeletal formulas.

Leyo: sorry for the outburst. Your English is so good, I forget it's not your first language. I do, however, wish to fight the corner of the GCSE or A-level student. It's easy to fail to meet their needs when we follow our intuition about what looks neatest.

Ben (talk) 11:57, 18 March 2011 (UTC)

Whoa, sorry for the edit-conflict-itis, Walkerma! Ben, I like your style there, including both information about the type of info and (one of my pet peeves of late) the origin of the 3D data. And I'm also warming to the idea of some sort of general-info link about the images. What if we had a simple page with a quick overview of the diagram styles, and then pointed to that single page from the infobox? Could either do it as a standard footnote in the banner above the images (we already do this for infobox refs, as "[1]" in cyclopropane) or else as a note in the infobox footer (where we already comment on other standards used in the infobox)? DMacks (talk) 09:38, 20 March 2011 (UTC)

Another way is to have a popup when user hovers over the image ("This is a skeletal structure."). With WP:POPUPS disabled, we already have this...the ImageName* fields are displayed (pointing but not clicking on the triangle form of cyclopropane pops up a "Cyclopropane - skeletal formula" box). However, with popups enabled, instead the pop-up box includes actions for the image description-page. If that page includes a statement about the image form and link to info about it (like Ben's), then that's visible and clickable to learn more (unlike the ImageName* boxes). However however, that only works for local images--images transcluded from commons do not have their file-desc page contents displayed in en.wp popups (compare the behavior of top-left(commons) vs bottom-left (local) at [7]). That's...not useful. DMacks (talk) 10:17, 20 March 2011 (UTC)

2-Bromo-1-chloropropane

I just stumbled across 2-Bromo-1-chloropropane, which is a bad example. Apart of the SVG bug, IMHO the image should be mirrored in order to have the 1 position on the left hand side and a skeletal formula is not the right choice here. Would a wedged bond to option of choice here to show that there is a chiral center? --Leyo 20:29, 20 March 2011 (UTC)

Our chemmos says:

For articles on racemates, only one enantiomer should be depicted ordinarily. In cases where no atom is stereogenic, it may be helpful to depict both enantiomers, e.g. [Co(ethylenediamine)3]3+.

I know the IUPAC says not to use "+ enantiomer", and I know that some other wikis (perhaps de?) prefer for both enantiomers to be included, but OUR MOS which we all agreed on, says to show only one enantiomer. As a side note, Jü (talk · contribs) has been going around "fixing" these images contrary to our MOS. Personally, if the bonds are not dashed or wedged at a chiral center, the article simply refers to a racemic mixture. You can emphasize it with a wiggly line if needed, but it seems unnecessary to me. --Rifleman 82 (talk) 20:49, 20 March 2011 (UTC)

I've uploaded a few structural formulas to Commons:Category:2-bromo-1-chloropropane.

Ben (talk) 19:32, 21 March 2011 (UTC)

Personally, I'd prefer it like this one (I do hate using my company's competitor site...). I always try to set SymyxDraw to do terminal and hetero hydrogens.  Ronhjones  ^(Talk) 22:08, 21 March 2011 (UTC)

Thank you Ben.

I also like this style (not the drawing quality). In most cases, I draw terminal explicitly, too. --Leyo 22:43, 21 March 2011 (UTC)

Article popularity statistics

Where can I find a list of WikiProject Chemistry or Chemicals articles, sorted by number of hits or popularity?

Ben (talk) 12:13, 20 March 2011 (UTC)

It's not sorted purely by popularity, but by the overall score (from importance + quality) - nevertheless, the assessment tables can be useful. In most cases the more important articles will come near the top, and will have more hits. Hits are per month, I think.

• • Chemicals
  • Chemistry

I'll ask CBM if we can get other search options. Hope this is helpful, anyway. Walkerma (talk) 15:22, 21 March 2011 (UTC)

Thanks, Martin, really helpful.

Ben (talk) 18:47, 21 March 2011 (UTC)

Silicon Categories

Delete? Plasmic Physics (talk) 08:32, 23 March 2011 (UTC)

category:organosilicon chalcogenides
category:organosilicon oxides
category:silyls
category:silicon hydrides
category:silicate esters

Chemical images for deletion

There are a bunch of chemical structure images listed for deletion at Wikipedia:Files for deletion/2011 March 23 if anyone would like to contribute to the discussions. ChemNerd (talk) 13:09, 23 March 2011 (UTC)

Chembox and Drugbox

To anyone interested in a possible merger of chembox and drugbox, or in the layout of drug articles: Template talk:Drugbox#Drugbox/Chembox merger vs. two infoboxes might be of interest. --ἀνυπόδητος (talk) 14:40, 26 March 2011 (UTC)

What is there to merge, there is nothing that the drugbox has that the chembox doesn't. Plasmic Physics (talk) 22:55, 26 March 2011 (UTC)

Special:ListFiles/Environmentalist and Historian

I tagged the ball-and-stick models uploaded by this new user as disputed. Does anyone experienced with such images willing to support him/her to create correct and high quality models? --Leyo 21:34, 27 March 2011 (UTC)

Quaternary compound

I've never heard this term used in the sense described in the article. Should this be rewritten, or redirected to Quaternary ammonium cation, or am I just uninformed? See also Ternary compound, Binary compound. --ἀνυπόδητος (talk) 16:33, 17 March 2011 (UTC)

I've never heard the term used like that. Binary, definitely; ternary, maybe; quaternary, never. However, I don't work in the superconductor area - see this example of use of the term. Walkerma (talk) 16:52, 17 March 2011 (UTC)

Anypodetos - Never seen that before - as for Walkerma's arsenic - yes I've seen that, but arsenic is in the same group as Nitrogen, so one gets N+, P+, As+, called quaternary, and with (of course) 4 substituents.  Ronhjones  ^(Talk) 23:35, 18 March 2011 (UTC)

Thanks, I've changed the article. --ἀνυπόδητος (talk) 10:54, 22 March 2011 (UTC)

Here are a page mentioning completely organic quaternary compounds and another mentioning some with transition metals. Here are a few pages highlighting the importance of quaternary central atoms in chirality (chemistry). In my experience, the bulk of work on chiral centres revolves around carbon; as opposed to solely concerning pnictogens as the article now reads.

"a quaternary compound is a cation consisting of a central positively charged nitrogen group atom"

The excerpt above is not only a hasty generalization because it specifies that all quaternary compounds are pnictogens but also because it requires them to all be cations even though the intermetallic ones have carbanions. By the way, is it really necessary for anything to be described as a cation and also as being positively charged? Would not it suffice to state that something is a cation and in brackets put "positively charged"? Either way, i think the current version of the article is an accidental fallacy. Warmest Regards, :)—_thecurran Speak your mind ^{my past} 08:55, 29 March 2011 (UTC)

A new nonflammable, high-strength, lightweight thermoplastic fluoropolymer

Hi. I work a bit in WikiProject Spaceflight and, in the process of adding and linking information about a new rocket engine today, I ran into a relatively new—and seemingly interesting—polymer material called nonburnite. I found only the one Wikipedia article that briefly mentioned it, so I added a redir page for Nonburnite that would take the reader to that page. I also did a bit of googling and found an abstract summarizing the material thusly: "a nonflammable, high-strength, lightweight thermoplastic fluoropolymer composite material, trademarked NonburniteTM, which is suitable for making reusable, reliable, low cost cryogenic tanks and structures for space flight service." I have added that particular quote, plus the rest of the abstract, to the nonburnite redir Talk page. It appears that NASA is funding some of this research, so have added the redir page to the spaceflight wikiproject. Perhaps it is of interest to your wikiproject as well.

So why did I write this? I have no idea what makes a new material become of interest to the materials science folks, or when it would be sufficiently notable for its own article, but did think I should draw this to someone's attention. I could not find a WikiProject Materials Science project, so thought I would just mention it here. It seems a bit of an interesting and capable chemical polymer compound to me. Cheers. —N2e (talk) 16:31, 25 March 2011 (UTC)

Indeed, we have no materials science project and this topic is covered here. We should wait when this material is properly described, particularly its chemical composition and structure, to see what it actually is - new composite by composition or by physical form (foam or alike), or etc. Materialscientist (talk) 06:17, 26 March 2011 (UTC)

Thanks very much for the comment. If I ever happen to note material added to a space-related article that better describes the material, I'll remember where I wrote this and get over here to point it out to the materials science/chemicals folk. Cheers. N2e (talk) 04:00, 30 March 2011 (UTC)

Nonylarenes

Advice is welcome on nonylated phenols. Seems esoteric, I know, but many commercial products (contraceptives, cosmetics) that are probably checked on Wikipedia contain "nonyl" groups, so we want to get it right. I am guessing that most nonylated compounds, such as nonoxynols are derived from branched C9's, as shown in nonylphenol (although that particular branching might be wrong) obtained from propene oligomers. I just dont think that industry has straight-chain nonene available cheaply, and if they did, the alkylation of phenol would produce the 2-nonyl derivatives. There are probably other articles in this area. But my main request is for input on how to represent such molecules, which are used as ingredients so often.--Smokefoot (talk) 12:57, 29 March 2011 (UTC)

(n00b question:) Aren't some of these made by telomerisation (2 x diene, 1 1-carbon fragment?). --Dirk Beetstra ^{T C} 13:00, 29 March 2011 (UTC)

I need to look into where the alkylating groups come from, but my money is on propylene oligomers.--Smokefoot (talk) 13:24, 29 March 2011 (UTC)

As the n00b in this subject .. I refrain from betting ;-). --Dirk Beetstra ^{T C} 13:31, 29 March 2011 (UTC)

Copper(I) fluoride

The guys on the chemistry project of de:WP recently dismantled [8] this articles german translation [9], after finding that most books list Cu(I)-F as only existant in melt and disproportionating upon cooling. Put together, there seemingly is no phase with sphalaerite structure of this substance. Regards, --Maxus96 (talk) 19:14, 29 March 2011 (UTC)

Ben - Where did the structure come from? I've certainly always thought (and taught!) that it doesn't exist. Chris (talk) 19:31, 29 March 2011 (UTC)

There was an old article doi:10.1002/zaac.19332100307 on crystallography of CuF, but without any explanation on its stability, sample preparation, etc. I couldn't find anything better upon quick search. Some theory articles mention fluorite the structure type, that would be sufficient for drawing, but would still need justification. Materialscientist (talk) 23:57, 29 March 2011 (UTC)

I think the image is based on the article Materialscientist links to.

No mention of CuF in Greenwood & Earnshaw. Might be worth deleting unless its existence is confirmed in the literature. How could an AB compound adopt the fluorite structure, which is AB₂?

Ben (talk) 01:57, 30 March 2011 (UTC)

"Fluorite" might have been my typo, thus strike out. Materialscientist (talk) 02:02, 30 March 2011 (UTC)

doi:10.1002/zaac.19332100307 was disproved by doi:10.1021/ja01637a039. Ebert/Woitinek measured Copper(I) oxide and Copper(I) chloride but not Copper(I) fluoride. --Orci (talk) 08:30, 30 March 2011 (UTC)

OK, well maybe one of our friendly admins should delete it then. Chris (talk) 09:57, 30 March 2011 (UTC)

IMHO the article does not have to be deleted, just updated. Copper(I) fluoride e.g. has a CAS registry number. --Leyo 10:12, 30 March 2011 (UTC)

Note: the article has been updated. Plasmic Physics (talk) 11:52, 30 March 2011 (UTC)

Well put some references in then. Where have you got all this from? You know the rules by now. I still think it should be deleted - having a CAS number does not mean it exists! Chris (talk) 18:31, 30 March 2011 (UTC)

I found some data here:[10] RolfSander (talk) 20:36, 30 March 2011 (UTC)

I did a SciFinder search for CuF. There are about 300 papers mentioning it, most of them theoretical or discussing the gas-phase CuF monomer or its complexes. A good, recent paper (Phys. Chem. Chem. Phys. (2010) 12, 8438-8445) has this to say:

Cuprous fluoride, CuF, was reported in the sphalerite structure (a = 4.264 Å) in 1933; however, there has been an absence of more recent reports. Whereas cuprous oxide is characterised by linear Cu coordination (O–Cu–O dumbbells), Cu(I) adopts tetrahedral coordination in chalcogenide compounds such as the chalcopyrite and kesterite family of materials. Furthermore, the heavier cuprous halides (CuCl, CuBr and CuI) adopt the sphalerite structure. The difficulty in synthesising CuF is likely to be related to the competitive formation of cupric fluoride (CuF₂) and complete dissociation into metallic Cu.

Might be worth keeping the article, if only to note that CuF is of dubious existence – better to say so explicitly than ignoring the matter. Could be converted to a subsection of copper(II) fluoride. Or perhaps we could create an article on nonexistent compounds. There's a book on the topic, based on W. E. Dasent, "Non-existent compounds", J. Chem. Educ. (1963) 40, 130–134. Aluminium carbonate is another simple compound that doesn't normally form.

Ben (talk) 20:55, 30 March 2011 (UTC)

The preparation of CuF is discussed in this patent: US 2817576  -- Ed (Edgar181) 21:01, 30 March 2011 (UTC)

• The current German version has merit and comes with references, the compound is unstable (nice example for HSAB theory) unless stabilized with ligands. there is as much to be learned from unstable compounds as there is from stable compounds, why are they unstable and how to stabilize them V8rik (talk) 21:04, 30 March 2011 (UTC)

Hydrogen chloride vs. Hydrochloric acid

Recently, a major reduction in content of the hydrochloric acid chembox occured. The predominant reason given was a widespread overlap with the hydrogen chloride chembox.

Key questions:

• Does hydrochloric acid merit a chembox?
• If it does, what information should it contain?

Plasmic Physics (talk) 08:22, 30 March 2011 (UTC)

The reduction is here, and the question concerns all acids obtained by dissolving, say, gas in water (HBr, HF, etc.). Some properties of hydrochloric acid might be better expressed with the table in the body. The question is whether we keep infoboxes for such acids and if yes, what information do we keep there. Materialscientist (talk) 08:47, 30 March 2011 (UTC)

The solutions do have some 'own' properties (i.e., not duplicating the ones from the free molecule) - I expect that hydrochloric acid has a different CASNo than hydrogen chloride (gas). Also, obviously, densities are different. Other properties do not really exist (molecular weight!). Problem with the acid is that they are concentration dependent, so one would need to take a 'standard' for these. I would suggest, use concentrated HCl for hydrochloric acid as the standard, not a dilution (some interesting dilutions could be in tables in the text). For hydrobromic acid also, use the normal concentrated one, not the fuming or a diluted version (though mention the fuming one in the text). Omitting the chembox completely would make these chemicals out of line with e.g. nitric acid (which obviously has a chembox which can not duplicate HNO₃. --Dirk Beetstra ^{T C} 09:03, 30 March 2011 (UTC)

Beetstra: Your example of nitric acid doesn't really work. The chembox data pertains mainly to hydrogen nitrate, not a solution of it. This is of the same style as hydrogen chloride, not hydrochloric acid. Plasmic Physics (talk) 11:44, 30 March 2011 (UTC)

That was exactly my point .. --Dirk Beetstra ^{T C} 11:48, 30 March 2011 (UTC)

Suggested new categories

Does anyone object to the creation of Category:Cyclopentanes and Category:Cyclohexanes which already have articles categorized in them, and are analogous to the existing category Category:Cyclopropanes? Also, should the categories be renamed like "Cylcopropane derivatives", etc.? ChemNerd (talk) 14:11, 28 March 2011 (UTC)

Sounds like it'll take a lot of time and effort to populate the categories - there are probably hundreds of articles that could fit in each of the two cats you propose. What do you expect the benefit to be? No point categorising for the sake of it.

Ben (talk) 18:59, 28 March 2011 (UTC)

I have to confess that my main reason to create them was that they were already in use. Presumably, someone has found them useful enough; but if consensus is that they are not beneficial, these categories should be removed from the articles they are placed on. ChemNerd (talk) 21:35, 28 March 2011 (UTC)

Someone will always invent a category, whether it's useful or not. These are hardly a functional group, I would say not create.  Ronhjones  ^(Talk) 21:45, 28 March 2011 (UTC)

I support the two proposed categories. Plasmic Physics (talk) 02:32, 29 March 2011 (UTC)

Depopulate these categories. There will be such an amount of compounds in there, that it is unhandleable. Are we now going to call steroids a cyclohexane? This is not a functional group, unhelpful. --Dirk Beetstra ^{T C} 08:49, 29 March 2011 (UTC)

OK. I won't create those categories. But while we're on the subject of categories (once again), I see that User:حسن علي البط has been adding to Category:Alkylbenzenes apparently anything with a carbon attached to a phenyl group (phenoperidine, difemerine, etc). Should these be removed? ChemNerd (talk) 11:50, 29 March 2011 (UTC)

Thank you ChemNerd, nice to see some consultation on category creation. It's a minefield.--Smokefoot (talk) 12:57, 29 March 2011 (UTC)

Regarding Category:Alkylbenzenes - IMHO that should contain only compounds which have alkylgroups on benzenes, and no other functionalities (toluene, ethylbenzene, xylene, etc.). Everything that has other functionalities should be in categories for aromatic compounds, and for the specific functional group. Otherwise a category 'alkylbenzenes' (like now) is becoming totally useless, unless we go into a huge break-up scheme where compounds get into sub-sub categories and mixed up, which makes the compounds very, very hard to find using the categories. --Dirk Beetstra ^{T C} 13:06, 29 March 2011 (UTC)

User:حسن علي البط has zero interest in serving the readership. This editor only in satisfyling a odd craving for contributing, and inventing categories is one way to appear to be useful (when in fact it is net destructive, in my opinion). One of these years, our administrative friends will step in and prevent this nonsense.--Smokefoot (talk) 13:24, 29 March 2011 (UTC)

I've emptied these categories, but there is still a lot of cleaning up to do. User:حسن علي البط is now made very aware of the result of his actions, and has acknowledged that he knows that. Another warning was left by DMacks about this as well. I found that there was an unanswered thread on User talk:حسن علي البط regarding this with pretty much the same message. It is now a final warning. --Dirk Beetstra ^{T C} 15:17, 29 March 2011 (UTC)

I have cleaned up the alkybenzenes category by removing everything that did not contain an unsubstituted alkyl group on the benzene ring. -- Ed (Edgar181) 12:27, 30 March 2011 (UTC)

I have weeded it out further, removing everything that had more than an alkyl as a functional group on the aromatic ring. It makes no sense to have 'bromotoluene' as an 'alkylbenzene', and not have 'benzylbromide' there - both have an aliphatic carbon connected to the aromatic ring. But then, having EVERYTHING with an aliphatic carbon in that category makes it impossible to go through. Starting to see alkyl groups as functional groups makes the basis of the set just completely impossible to go through, and in the end we will get to 'aromatic compounds with 2,4-dimethyloctyl groups' or whatever. Keep alkylbenzenes for compounds which are just that, and for the rest, ignore the alkyl part - it will become impossible to go through otherwise. --Dirk Beetstra ^{T C} 08:37, 6 April 2011 (UTC)

Your views wanted

The views of folks interested in articles about chemicals are particularly wanted at Wikipedia talk:WikiProject Pharmacology#RfC:_Are_the_medication_articles_too_technical_and_if_so_what_should_we_do_about_it.3F. Please have a look and share your thoughts on how to best structure articles about medications. WhatamIdoing (talk) 17:01, 3 April 2011 (UTC)

The scheme

I would like to talk with everyone intersted in categorization of chemical compounds. First I admit and confess that I was to some sort selfish and that I ignored discussing my opinion with editors and that was because I was ambitious and energyful. Now I need your help. That is right my work was haphazard but I promise I will change that.

My point of view is summarized in the following:

First, on the large scale:

• Category:Cyclic compounds which is divided into:
  • Category:Heterocyclic compounds and
    • Category:Nitrogen heterocycles
      • • Category:Nitrogen heterocycles (1 ring), 2 rings, 3 rings ...etc.
    • Category:Oxygen heterocycles, ...etc.

• • • Category:Non-heterocyclic compounds which is divided into:
      • Category:Cyclopropanes for compounds containing cyclopropane moiety,
      • Category:Cyclobutanes for compounds containing cyclopentane moiety,
      • Category:Cyclopentanes, ...etc.

For that I created many categories to enable simplicity in handling chemical compounds even for beginers and amateurs, since each category with its main article would explain itself effectively.

Second, on the tiny scale: I think that categorizing compounds may be related to anatomy in medicine which describing each organ (here chemical group or moiety) with the most possible details. Sucategorization enable us to differnaite between compounds even the category contain only one member. This point is what gives power to Wikipediak as we can look for a certain compound by only knowing that it contain a certain group enen like Cyclohexane moiety. What do u think? User:حسن علي البط --حسن علي البط 06:09, 6 April 2011 (UTC)

I disagree with the '<element> heterocycles (# rings)', that is too detailed, as is having everything which has a cyclopentante or a cyclohexane ring in it categorised as such. Yes, everything in the category for steroids has also a cyclohexane ring and likely a cyclopentane ring, but if they are already in the steroids, having them in the cyclohexane / cyclopentane groups is not making them easier to find. Before that becomes useful it would need massive sub-categorisation, where it then becomes a tree which is not suitable for browsing anymore. If there is a category cyclohexanes, then that should be limited to compounds which are simple derivatives of that, like bromocyclohexane, cyclohexanol, maybe decalin, but not contain steroids, nor contain a huge sub-tree of divisions. --Dirk Beetstra ^{T C} 08:06, 6 April 2011 (UTC)

Sir, steroids are classified under fused ring systems as Category:cyclopentanophenanthrenes which will -on the opposite of your speak- make it easier to be founded. --حسن علي البط 04:20, 7 April 2011 (UTC)

Well, a LOT of editors disagree with the recategorisations, and I am one of those (see also Cacycle below). There is NO consensus for what you and others are applying. As has been asked to other editors, STOP with all recategorisations, and discuss and get consensus (we all know, consensus can change - but there is no indication there is at the moment)! --Dirk Beetstra ^{T C} 07:19, 7 April 2011 (UTC)

Please see Special:Contributions/حسن_علي_البط, this user has started a massive categorization campaign with many (if not all) new categories being nonsensical or useless (e.g. any complex drug molecule that has an OH group anywhere, even as hemiacetal, was added to Category:Alcohols). Please could somebodyvrevert this and stop that guy? Thanks, Cacycle (talk) 06:50, 7 April 2011 (UTC)

It seems you already reverted and warned? --Dirk Beetstra ^{T C} 07:19, 7 April 2011 (UTC)

Blocked 24 hours. DMacks (talk) 16:54, 7 April 2011 (UTC)

IRC meeting to discuss possible addition of Jmol links

I met with Robert Hanson (chem professor and Jmol developer) at ACS Anaheim, and he has said that there is now a reliable, public website (run by NIH), providing Jmol renditions of molecules in 3D. These are apparently given a basic energy minimisation (though I'm not sure of the method), so they should (other than in a few unusual cases) represent the "normal" shape of the molecule in 3D. As I understand it, this would allow us to provide our readers access to minimised 3D structures that can be manipulated, but without needing to download Jmol.

Dr. Hanson has proposed three possible options:

1. Provide an external link in the chem box to a college server that takes the Wikipedia SMILES string in its URL, goes to the NIH, and returns a 3D model in a new page.
2. Run a process that installs in Wikipedia Commons a full set of MOL files for existent SMILES strings for compounds in the Wikipedia, and then not access the NIH after that. In principal, if the Jmol JAR files were on the Wikipedia server, this would then avoid any need for an external link.
3. Have a process that checks the Commons for a file, and only goes to the NIH if that file does not exist. Perhaps installing it in the Commons when it doesn't find it. Then displays a page for the model.

I have proposed that we discuss this on IRC at #wikichem, Tuesday April 12 at 1500h UTC (11am US Eastern Daylight Time, 1600h British Summer Time). You can also comment below. Walkerma (talk) 16:45, 7 April 2011 (UTC)

Comments

I've put up a demo at [[11]]. Now, that's the basic idea. I've worked out three ways to show molecules. We could just produce an external reference to a model, like this: [cholesterol 3D model]. (That's a URL-encoded SMILES string.) So actually, all we would need to do is enter the SMILES string like that into an external reference, and the job would be done. I don't know what the behind-the-scenes capability of Wikipedia is exactly, but I was thinking a popup window would be nicer. That, though, requires a <script> tag. Can we do that? Do we want that? Hansonrstolaf (talk) 19:18, 7 April 2011 (UTC)

• Collides with faculty meeting. I'll try to remember to leave an irc session open and read later. I've started using jmol in my intro-orgo class, the ones who have bothered to try it seemed to find it useful and easy to use to analyze 3D structures, even complex ones that can't be diagrammed from any one perspective cleanly. It can be done completely webserver-based (no downloading of files, programs, or installing plugins), so all they need is a browser with java enabled (I tested on Mac and Windows, with Firefox, Safari, and Explorer). There is a MediaWiki extension that allows use in-wiki (Walkerma's #2 "in principal")...it's been long discussed but not made available on wikipedia itself. Until that happens, I don't see a technical advantage to putting the .mol on wikipedia. It's certainly useful data, but it's not really usable in the context of wikipedia. As standardly configured, the web-based jmol only appears to be able to access structure files on the same server. If that were fixable, could have the applet itself hosted somewhere, with link to it including CID or other index key and then server pull the structure file from...wherever. I only mention CID as example because pubchem has SDF available at URLs using that token. DMacks (talk) 17:41, 7 April 2011 (UTC)

What we are talking about here is "post-mediaWiki-Jmol-extension." That was a fine idea, but it was never right for the Wikipedia, because it required applet initialization when a page is loaded. We realized several years ago that that would never fly with Wikipedia. This is very different. We have figured out how to deliver structures with no file base on any server and to deliver them with no codebase on the Wikipedia server. No cross-browser issues, because we are using PHP to deliver the files, not JavaScript. For example, here's the structure of [cyclohexanone], just using its name. I don't propose doing that so much from Wikipedia, because the names must be of known compounds -- OK, so there are 80,000,000+ compounds in the NIH database, but still, it's not CERTAIN that a structure will be found. You can add a bit of scripting to make it more interesting. Here is one of my favorites, where now I am starting an animation from the tag: [cyclohexane ring flip].Hansonrstolaf (talk) 20:56, 7 April 2011 (UTC)

• There is also interest to use jmol to display protein structures. Boghog (talk) 18:23, 7 April 2011 (UTC)

PDB files are no problem. You use pdbid=xxxx instead of model=xxxxx, like this: [1CRN 3D model] Hansonrstolaf (talk) 19:18, 7 April 2011 (UTC)

• If seeing these structures requires any extra plug-ins/software/etc., then the links must be plainly labeled per WP:EL#Rich media. If by "java", DMacks means "Javascript", then I'm not sure whether that will be necessary, but Flash video, for example, is. WhatamIdoing (talk) 18:31, 7 April 2011 (UTC)

We are talking about links, using Java for the applet. No plug ins. No flash. Not even any JavaScript if we don't want to use it. Just anchor tags. We do a lot of testing to make sure this works on virtually every browser. Of course, now the iPad is out because it does not support Java, and no delivery on mobile devices (yet -- I do have a plan for that...).Hansonrstolaf (talk) 20:56, 7 April 2011 (UTC)

• Jmol in Wikipedia would be nice, but I'm very wary of generating 3D structures from connectivity (SMILES or similar). Most molecules we'd want to exhibit have many conformers, only some of which are realistic or important. The minimisation procedure would have to explore all of conformational space to get the global minimum. I might be unduly cynical, but I bet it just starts with a ridiculous geometry based on SMILES and finds the nearest local minimum. I think it's extremely important that all our structures (2D or 3D) are accurate, and based on published experimental or computational results. Otherwise, Wikipedia would become a giant automated chemical structure OR factory. I've been using Jmol on my website for personal revision and to share with classmates: http://www.benjamin-mills.com/chemistry/structures/all.html. It can be really useful, but we must consider the pitfalls. --Ben (talk) 18:39, 7 April 2011 (UTC)

We are using the NIH CACTVS site, and I have to say that although I was skeptical about it returning 3D structures from SMILES, I'm now sold. It is VERY good. I haven't found a bad structure yet. I don't know exactly how they do it. But it's very impressive. For virtually any compound of interest to Wikipedia, you can also just supply the name. Also, we could read files straight from Wikipedia Commons if they are deposited there. Martin and I were talking about this at the ACS meeting, and in some ways that might be the ideal -- moving to having MOL files in Wikipedia Commons. But they really can be anywhere. For instance, here's one of those Benjamin-Cummings models at your site, Benjah-bmm27: [Ru(CO)H2(PPh3)3]. How cool is that?? Not that I'm suggesting we pull molecules from commercial sites at all. Just demonstrating the power of this little PHP script. One question I have is this: Could we put a little PHP script on a Wikipedia server and just deliver the files "in house"? Here are some more examples, from SMILES strings: [buckyball from SMILES] [taxol from SMILES] Hansonrstolaf (talk) 22:30, 7 April 2011 (UTC)

Thanks to Walkerma for alerting me to this discussion. The IRC meeting is midnight in Melbourne and I am not a late bird. My brain would probably be switched off by then if I stayed up for it. I have added a link to this discussion at Wikipedia:Using Jmol to display molecular models, which is where the using jmol on WP idea was first discussed. It would be great to have jmol images in WP articles and keeping the files on Commons is a good idea, if the files can be released under an open license. I want the jmol image to be in the article itself so the reader can look at the image while reading the article, not going to a separate page as the examples above. Over the years I have dispaired of this ever happening. I am not entirely clear of what is being proposed above, but I have one question - can this idea be trialled on WP without getting new technical stuff added to mediawiki by the WMF developers? I talked to Tim Starling, a WMF developer, about this years ago and I know he had many concerns. I have not talked to him about it recently as he now lives in New South Wales, not Melbourne. If we could have something to show him, he might be convinced. I will try to add more before the IRC meet. --Bduke (Discussion) 22:23, 7 April 2011 (UTC)

If by "Jmol image" you mean "interactive applet," that's a problem for being within the page. The applet can take several seconds to load the first time of a browser session, and that would slow page loading immensely. I am not advocating that.Hansonrstolaf (talk) 22:28, 7 April 2011 (UTC)

• The first option is a quicky .. it could just re-use the smiles which is already available from both {{chembox}} and {{drugbox}}. Only 'issue' is that it then becomes a field in the identifiers box, which is not technically the right way forward. I would be against moving the smiles .. and duplicating it is similarly an issue. I'll play for now a bit with {{chembox SMILES}} - adding a link there. Note: can this run from InChI? That is probably more reliable than the SMILES. --Dirk Beetstra ^{T C} 12:08, 8 April 2011 (UTC)

  Added it to the SMILES in the box for now, so editors can quickly see what is happening and if/when it breaks. This is not the optimal place to display this, that needs further discussion. May revert this change after the discussion. Will try to be there on Tuesday, but can't promise it yet. --Dirk Beetstra ^{T C} 12:14, 8 April 2011 (UTC)

  Thanks Dirk, for letting us see how it looks in any ChemBox! At least as an ignorant organic chemist, this looks nice! Part of the discussion will be - if we like these renditions, we need to decide the best way to link to them. Also, thanks Hansonstolaf for responding to the questions. Walkerma (talk) 13:30, 8 April 2011 (UTC)

  You're welcome. This is something that can be implemented immediately - this is not saying that one of the other two options is not better or nicer, or that this should be displayed here. Please have a look around to see if it really goes well for most compounds or if there are any obvious breakages in the system. --Dirk Beetstra ^{T C} 13:37, 8 April 2011 (UTC)

  That's certainly something like the idea I was thinking of. It's "Jmol" not "JMol", by the way. Ultimately I don't think it belongs hidden in the SMILES record. True, it's based on SMILES, but people should not have to show the SMILES just to see the 3D structure. That should be transparent to the user, I think. Can anyone tell me why, in the DrugBox of Paclitaxel there is no SMILES shown, and instead two links, one of which is to a commercial site? I don't see in the page code where that is coming from. Hansonrstolaf (talk) 17:15, 8 April 2011 (UTC)

  InChI vs. SMILES. InChI keys should work, but I think then the structure must be in the database; with a SMILES string the structure is not looked up -- it is just calculated on the fly. I'll check on InChIs. By the way, what does it mean that there are two InChIs listed for Cholesterol? Hansonrstolaf (talk) 17:15, 8 April 2011 (UTC)

  InChI is working now: [taxol from InChI] (Note the need to escape "+" as %2B) Hansonrstolaf (talk) 14:43, 9 April 2011 (UTC)

  Another thought that is really a different issue. An interesting thing we can do with Jmol is to compare two SMILES representations (or a SMILES and an InChI) and report whether they are the same structure (or if not, how they are related). I don't know how much validation like that has been done in Wikipedia, but the opportunity is there to do that now, using Jmol. Hansonrstolaf (talk) 17:15, 8 April 2011 (UTC)

  By the way, just stumbled on a VERY odd invisible character ​ in the SMILES string of Sucrose. Hansonrstolaf (talk) 17:51, 8 April 2011 (UTC)

• Being able as shown above to get the Jmol image displayed from the infobox is certainly better than anything we had so far. Congratulations to all who have helped to get us this far. However, because it is displayed in a new tab one can not look at the Jmol and the article at the same time. Is it possible to display the Jmol in a new window and make it a small window (not much bigger than the Jmol box) so the user can move it around on top of the article window? --Bduke (Discussion) 22:01, 8 April 2011 (UTC)

It seems to me a floating window on the page or to a div would be extremely cool. This would require AJAX to the Wikipedia server, I think, but if that were possible, then we could do that as well. (I think it could also be done with an IFRAME, but that's pretty retro.) Hansonrstolaf (talk) 14:57, 9 April 2011 (UTC)

• To summarize progress of the day: We can now access 3D models from PDB IDs, InChI strings, SMILES strings, or full http:// model file location descriptions from Wikipedia as external links. Note that in the case of InChI and SMILES strings there is no "file" being loaded -- the NIH resolver is calculating the structure on the fly and returning it. (Really quite amazing!) One needs to take care to ensure adequate escaping: "+" to %2B, "%" to %25, "[" to %5B, and "]" to %5D, for example. I've added &title and &caption options as well (see [http://chemapps.stolaf.edu/jmol/jmol.php]). The service is set to time out after 20 seconds if there is no return from NIH. Hansonrstolaf (talk) 14:57, 9 April 2011 (UTC)

Which categories for 2,5-Xylidine

Which categories should 2,5-Xylidine be in? take a look at the history... (it is not the only xylidine which have lost its categories) -- Christian75 (talk) 18:14, 9 April 2011 (UTC)

I don't know why I removed 'anilines', must be a mistake. I did remove alkylbenzenes per a discussion above. --Dirk Beetstra ^{T C} 19:40, 9 April 2011 (UTC)

Help needed with stubs

Dear WP Chemicals members - over at WikiProject Stub sorting we have a problem! There used to be a stub category Category:Natural phenols and polyphenolic compound stubs, but, seeing as there was no related permanent (non-stub) category it was split into its two separate parts, Category:Natural phenol stubs and Category:Polyphenol stubs. Un fortunately, there are no stub sorters who can easily tell from the article which of the stubs should be in which category - most of the articles don't directly say, but instead refer only to the specific type of chemical (I wouldn't know the difference between a furalflavonol and a glycoside if they came up and introduced themselves, let alone know which was a polyphenol, if either). Could any of you who specialise in organic chemicals have a look through Category:Natural phenol stubs and see which ones should be marked with {{polyphenol-stub}} rather than (or as well as) {{natural-phenol-stub}}? Cheers! Grutness...wha? 01:39, 10 April 2011 (UTC)

Category:Chemical element symbol templates

Template:Protactinium has been nominated for deletion; see WP:TFD#Template:Protactinium. We (or at least I) would like to know more about the templates in this category, and the pros and cons of wikilinks in chemical formulas. — This, that, and the other (talk) 10:20, 12 April 2011 (UTC)

Drugbox/Chembox merger vs. two infoboxes

Could an uninvolved admin close the discussion at Template talk:Drugbox#Drugbox/Chembox merger vs. two infoboxes? I think the outcome is pretty clear, but I'd prefer it the formal way – this question (or similar ones) has been brought up quite often, and never led to anything. We really should start doing things this time. Thanks, ἀνυπόδητος (talk) 14:35, 13 April 2011 (UTC)

Category:Chemical substances

Category:Chemical substances has been proposed to be merged into Category:Chemical compounds. 65.94.45.160 (talk) 06:04, 30 April 2011 (UTC)

"Typo-fixing"

Ebe123 (talk · contribs) has run through quite a few of our articles. I worry that too many useful links have been removed. --Rifleman 82 (talk) 17:02, 1 May 2011 (UTC)

They were asked to stop using AWB (at least the way they did, which was damaging indeed) and they seemed to comply. Materialscientist (talk) 07:41, 4 May 2011 (UTC)

Avoiding an edit war

Have a look at the edit history for Trimethylsilyldiazomethane‎. Plasmic Physics (talk) 13:36, 6 May 2011 (UTC)

I've continued your reversions, thanks Plasmic. Anyone can see from the titles of the references that trimethylsilyldiazomethane is the usual term used in the literature. Diazo(trimethylsilyl)methane is not incorrect, but seems unnecessary and unpopular. User:Daniblanco and 150.244.197.77 seem to be pushing a very minor nomenclature POV. Tedious nonsense. --Ben (talk) 14:30, 6 May 2011 (UTC)

"Trimethylsilyldiazomethane" is the common name and I agree that it is the one we should use. -- Ed (Edgar181) 14:32, 6 May 2011 (UTC)

Chemical substructure articles

These new articles about chemical fragments seem non-notable and quite useless to me. I'm inclined to propose them for deletion. Any thoughts? ChemNerd (talk) 13:38, 9 May 2011 (UTC)

• 2-methylphenoxy
• 3-methylphenoxy
• 5-methylphenoxy
• Methylphenoxy

Delete, before you know it, we get 2-methyl-3-isopropylphenoxy ... --Dirk Beetstra ^{T C} 13:42, 9 May 2011 (UTC)

Semi-useless but not completely. Let me change them to redirects to cresol. Its almost impossible to delete stuff in Wikipedia and by changing to redirect, we occupy that titlespace.--Smokefoot (talk) 13:44, 9 May 2011 (UTC)

Redirecting and merging into cresol is a nice solution. Thanks Smokefoot. ChemNerd (talk) 14:18, 9 May 2011 (UTC)

Ordering elements in chembox formulas

{{Chembox}} allows to autogenerate chemical formula by specifying elements (C = 1, H = 2, etc.). This is convenient (mass is auto-calculated and the input is simple) and therefore is used in many articles, but results in weird formulas like Cl₃W, etc., because the ordering is alphabetic. This ordering is accepted by suppliers but not scientists. Proposal: change it to the IUPAC system, where the elements are listed in order of their position in the periodic table, read from bottom to top, left to right, and hydrogen between groups 15 and 16. Beetstra suggested to bring this here. Please comment/vote. Materialscientist (talk) 07:41, 4 May 2011 (UTC)

Note, the adapted system is the 'Hill system', which is a common way of ordering the elements. There are indeed other ways of ordering, but all of them have different effects/difficulties. I myself would look for chemical formulas in google by applying the Hill system, which now should give me hits including the Wikipedia page. Ordering can be easily adapted by 'sorting' {{Chembox Elements}} (fully protected, but one could just make a sandbox to test first). Note2: would be nice if we could also force this template to do 'exact mass' as it seems there is some interest in that number sometimes. --Dirk Beetstra ^{T C} 07:52, 4 May 2011 (UTC)

(EC) I assume the Hill system is used. This is perfectly fine for organic chemicals. For inorganic chemicals, some formulas might look a bit strange.

BTW: Could you please give some examples of articles using this method? As far as I see, it is not documented on Template:Chembox. --Leyo 07:56, 4 May 2011 (UTC)

Yes I meant Hill system. A quick example that came to mind is acetone. There were attempts to use it for inorganics and salts. They were reverted/replaced with another syntax, that is specifying |Formula = and |MolarMass= Materialscientist (talk) 08:06, 4 May 2011 (UTC)

Suggestion: we could make it so that if C > 0 & H > 0 that it adapts the Hill system, otherwise another system .. (there are some inorganics which have both an inorganic H ánd an inorganic C .. but that is pretty minimal). --Dirk Beetstra ^{T C} 08:20, 4 May 2011 (UTC)

What about compounds like lithium methanide? Under Hill's, it would be CH
₃Li, under IUPAC's, it would be LiCH
₃ Plasmic Physics (talk) 01:47, 5 May 2011 (UTC)}}

Under any choice there are going to be oddities .. also consider 'MeLi' (I would not write LiMe). I think (I use the word 'think'!) the previous consensus was to use the Hill system .. there are pro's and con's to all .. difficult choice. --Dirk Beetstra ^{T C} 07:19, 5 May 2011 (UTC)

For me at least, formulae generated according to the Hill system tend to appear odd on more cases than not for non-carbohydrates. The IUPAC system generates formulae that are overall more agreable with other users besides myself.

P.S. "MeLi" is an abbreviation for the name methyllithium, where the covalent character of the molecular orbital between lithium and carbon is emphisised. Alternatively, others prefer to stress the ionic character and name it lithium methanide instead, with the corresponding abbreviation "LiMe". Note that an abbreviation in any case is distinct from a stoichiometric formula. Plasmic Physics (talk) 20:20, 5 May 2011 (UTC)

What has happened to this discussion? Plasmic Physics (talk) 10:12, 12 May 2011 (UTC)

Templates

What is the purpose of templates with a name structure Template:(Element) compounds? Example: Template:Mercury compounds. Plasmic Physics (talk) 10:09, 12 May 2011 (UTC)

I guess to make a compact selection out of a category:(Element) compound. Materialscientist (talk) 22:29, 19 May 2011 (UTC)

Why not just go to the corresponding category? Plasmic Physics (talk) 00:05, 20 May 2011 (UTC)

(ec)I can see technical differences (e.g. the category content is volatile and can't be watched, though it is autoupdated), but I don't know if all those templates are needed. Materialscientist (talk) 00:21, 20 May 2011 (UTC)

I think we need to discuss this thoroughly here. There seems to be some overlap with chembox other, and unless some editorial discretion is exercised, the lists are meaningless and unmaintainable. For example, are we looking at the principle compounds? Or all the binary compounds? Surely not everything! I'll ask the editor to come by. --Rifleman 82 (talk) 00:18, 20 May 2011 (UTC)

OK, but beware, there is more than one editor. Example {{Silicon compounds}}. Plasmic Physics (talk) 06:06, 20 May 2011 (UTC)

Hi! I have recently created several compound templates. I have just followed the trend, noting that some elements have templates but others don't. I am not a chemist; I did the work for the sake of completeness. Feel free to correct it. Best regards, Lamro (talk) 06:43, 20 May 2011 (UTC)

Hmm .. though I see for some that it is interesting .. if we push this to completeness we may end up with a template larger than the page Carbon if we create {{Carbon compounds}}. I am sorry, I think that these should be removed, too difficult to maintain. If anything, maybe the articles should link to 'list of <element> compounds' (though that would indeed just be a representation of a category, only less volatile, and still having the same incompleteness problems). --Dirk Beetstra ^{T C} 08:07, 20 May 2011 (UTC)

Now that we've decided, who will enforce? Plasmic Physics (talk) 12:18, 24 May 2011 (UTC)

I would like to second Beetstra. I don't think templates that cannot reach completeness are useful. IMHO we should restrict ourselves to templates like {{Group 12 elements}}. --Leyo 12:33, 24 May 2011 (UTC)

WP:TfD for the whole set? --Dirk Beetstra ^{T C} 12:46, 24 May 2011 (UTC)

It sounds good. Plasmic Physics (talk) 13:04, 24 May 2011 (UTC)

Category:Hypothetical chemical compounds

What about creating Category:Hypothetical chemical compounds for such articles? --Leyo 12:13, 24 May 2011 (UTC)

I think it is a good category to create. -- Ed (Edgar181) 14:13, 24 May 2011 (UTC)

Yeah, nice idea. Go for it. --Ben (talk) 15:07, 24 May 2011 (UTC)

It is not really my idea (see de:Kategorie:Hypothetische chemische Verbindung). --Leyo 16:43, 24 May 2011 (UTC)

New template created

Check template:Ionbox created by Graeme Bartlett. Plasmic Physics (talk) 06:39, 28 May 2011 (UTC)

Drug Box on Belomycin

(If this is the wrong forum for this, feel free to move it to the correct forum ! )
I just made a cosmetic change on the drug box for Bleomycin , as I've never worked with a drug box before I've left a note over there On the talk page. Feel free to take a look, and if I've botched it up, feel free to change it and let me know where I erred. Thanks
KoshVorlon' _Nal^uboutes _Aeria ^Gloris 18:05, 30 May 2011 (UTC)

Reposting from Wikipedia:Village pump (miscellaneous). Regards, RJH (talk) 15:40, 31 May 2011 (UTC)

Mass uploading

I have just uploaded, with the author's permission, over 200 files from here. Some of you may find them helpful in certain articles. --Chemicalinterest (talk) 13:06, 31 May 2011 (UTC)

That is really nice. Hopefully we can use some these images because some are often superior to ours current ones. It does not appear that the site is spamy or promoting any agenda aside from amateur science. If we link to that site and then the site becomes weird in some political-religious-business way, that could be uncomfortable. The associated explanations are nice but possibly incorrect in places. --Smokefoot (talk) 13:44, 31 May 2011 (UTC)

I've started adding those images to the articles. Elements images we have better or equal, but the situation is reverse with most compounds. Thanks a lot for uploading them. Materialscientist (talk) 13:56, 31 May 2011 (UTC)

@Chemicalinterest: Could you please link a gallery or upload log with those images? --Leyo 14:22, 31 May 2011 (UTC)

Here is a gallery of Chemicalinterest's Commons uploads. Definitely some useful photos there. -- Ed (Edgar181) 14:42, 31 May 2011 (UTC)

Yes, indeed. Two concerns: a permission via OTRS might be advisable and the link given in some file description pages does not work. --Leyo 15:58, 31 May 2011 (UTC)

Any broken links are the result of typing errors. --Chemicalinterest (talk) 16:21, 31 May 2011 (UTC)

Here is what I received in response to an upload request:

Hello, By this I confirm that you may upload these images in Wikipedia articles.They are available for public domain. Just provide a link to their origin and then it is OK to me. Regards, Wilco

I'm not sure what OTRS means, but the author has an email address on their website.--Chemicalinterest (talk) 16:23, 31 May 2011 (UTC)

See WP:OTRS. --Leyo 20:23, 31 May 2011 (UTC)

Did you forward the e-mail? See WP:PERMIT for more information.

In my opinion you really need to do this in order to keep these images. --Leyo 09:14, 7 June 2011 (UTC)

The images look very nice - a really good contribution. In the case of chromyl chloride one can see that it is volatile from the reddish head-space. It is probably worthwhile weeding out some questionable images, or at least explain to readers what they are viewing. The new image of nickel(II) sulfate does not jive with the existing image, which is a nice sample of the hydrate. In that case, I would remove the newer image since we are unsure about the state of hydration. In the case of niobium pentachloride, the new image shows a liquid, but the material is yellow solid, so that one also is difficult to reconcile. I think that really good phosphorus pentasulfide (rarely seen) is actually yellow vs the cruddy brown shown, but that image is still the best that is out there. I hope that other chemists will look over the assortment uploaded by ChemInterest to check for potential issues.--Smokefoot (talk) 01:00, 1 June 2011 (UTC)

Yess, excellent collection! Is File:Sodium molten.jpg really currently in the liquid state in the image (hand holding something around 100 °C), or just blobs that had melted and then cooled into that shape? It's easy to do that latter and get something that looks exactly like this. If it were currently liquid, the blobs usually rapidly stick together to make a large pool. DMacks (talk) 13:47, 7 June 2011 (UTC)

I think if it were molten it'd be shiny. At least, when I distill stuff that's how it looks, blobs of molten shiny metal going round and round. --Rifleman 82 (talk) 18:24, 7 June 2011 (UTC)

Thanks a lot for getting these uploaded, ChemInterest. Walkerma (talk) 16:14, 7 June 2011 (UTC)

OrganicBox templates up for deletion

{{OrganicBox hbond donor}} and {{Style OrganicBoxTD 2}} have been nominated for deletion. 65.95.15.60 (talk) 06:35, 6 June 2011 (UTC)

Commons:Commons talk:WikiProject Chemistry/Categories#Plurals and derivatives

May I direct your attention to this important discussion on the categorization on Commons? --Leyo 16:17, 8 June 2011 (UTC)

Bismuth subsalicylate's chemical infobox

I noticed that someone added a ChEMBL number to the infobox in the Bismuth subsalicylate article that looks legitimate. However, a red X now appears next to it. Could someone please verify this addition and update the bot responsible for adding checkmarks and red X's to these infoboxes if the addition is legitimate? Thank you. I am a computer engineer, not a chemist. Therefore, I do not want to falsely verify this stuff because I am not qualified to do so. Jesse Viviano (talk) 22:22, 8 June 2011 (UTC)

List of extremely hazardous substances for deletion?

I'm thinking of proposing this list for deletion. It's full of errors, either because the original list [12] is poorly defined to begin with (what's "organorhodium complex PMN-82-147", with no cas number?), or because of editors adding their favorite compounds with no basis. For example, ricin's not in the real list, as are others I've removed today. This list "article" requires a rather dedicated effort to keep it in line with the official list which does vary over time. I would opine it's not really maintainable, and we are better off without this "article". Comments? Is there any value in having this "article" in WP? --Rifleman 82 (talk) 22:04, 12 June 2011 (UTC)

It's well intentioned but naive and invites original research and soapboxing, IMHO. Maybe convert the article to MSDS or some related topic. Closely related would be Highly hazardous chemical.--Smokefoot (talk) 00:15, 13 June 2011 (UTC)

Not good, delete it. It's not a worldwide view, just US only; some of those chemicals I would use any day, others I wouldn't touch with a barge pole. Allyl alcohol is in, but Dimethyl sulphate is not; Chloroform is in, Carbon tetrachloride is not! Such a list could give entirely the wrong impression.  Ronhjones  ^(Talk) 19:51, 14 June 2011 (UTC)

Considering that many of our chemistry lists can vary over time this isn't a unique problem. Personally I think this list is manageable. Just like any type of encyclopedia topic, things change over time and we need to keep our articles up to date. As for the content of the article, the fact that some authority has seen fit to include items that are "poorly defined", or that give "wrong impression" is not a reason to delete in my opinion. The fact that it only applies to the United States isn't a reason to delete either - we include all kinds of topics that are relevant only to much smaller countries that the US. The only real consideration, in my opinion, is whether the list itself is notable or not. We have an article on the law that the list is based upon, Emergency Planning and Community Right-to-Know Act. Maybe it is sufficient to simply supply an external link there to an official list? -- Ed (Edgar181) 20:17, 14 June 2011 (UTC)

I do not see how OR is coming into play here. It is a list and occasionally people add new chemicals to the list when they should not. It is useful to have this list, linking the chemicals on the list to articles on that chemical is great added value which the original list does not have. It is also disturbing that a number of chemicals listed still have not yet been identified. That should be addressed. But OR? How! V8rik (talk) 20:28, 14 June 2011 (UTC)

The list is really long, and the official form of the list does not lend itself to wikilinking. I first tried to validate the list one-by-one according to the reference, but I got confused after a while. I tried to prepare the list again according to the reference from scratch, but gave up after half an hour. If it were easily maintainable, I'd be in favor of keeping the wikilinked list. It's not really encyclopedic in itself but it is a convenient directory (WP:NOT#DIRECTORY notwithstanding). I would rather delete the "article" than keep it in its present unreliable form. If we do keep it, can we divide the task of maintenance and verification so that the problem is a little more manageable? --Rifleman 82 (talk) 21:05, 14 June 2011 (UTC)

US Environmental Protection Agency would like to help improve some pesticide chemical pages

Hello. As indicated by my user name, I work for the United States Environmental Protection Agency. Given the popularity of Wikipedia and the sometimes contentious nature of things we regulate (e.g. pesticides), I proposed to my management that EPA somehow get involved in Wikipedia content when facts related to the agency's purview are substantively misstated here. I finally got the necessary approvals and am now trying to recruit Wikipedians who can help incorporate our comments into the content. The first topic we hope to clean up is Clothianidin. Since this is USEPA's first official foray into editing Wikipedia, we're taking a conservative approach to editing content. I've posted the recommendations from EPA's subject matter experts on my talk page, and I'm hoping I can get input from this group about our approach and suggested edits. Please drop by and comment if you're interested. USEPA James (talk) 14:48, 16 June 2011 (UTC)

I invite anyone interested in pesticide chemicals to comment on substantial changes I've proposed on the clothianidin talk page.USEPA James (talk) 21:35, 22 June 2011 (UTC)

Chemicalize for MediaWiki

I chatted with Alex Allerdyce from ChemAxon, a chemical software company, while I was at the ACS meeting in Anaheim. They are a commercial operation, but they are very supportive of education and also of volunteer communities like Wikipedia, and they give much of their software away for free to people like us. Some of it is really only suitable for big pharma, but they have a lovely toy called "Chemicalize" that marks up an article with structures. For example, you can hover over a name like capsaicin, and it shows the structure for you. If you click on a wikilink, the new page is "chemicalized" as well. You can see the effect on these pages:

• Menthol
• Diels-Alder reaction

As a result of our discussion, they are putting together a MediaWiki extension for Firefox, which (as I understand it) would operate much faster than going via chemicalize.org. Any chemist who wanted to "chemicalize" their Wikipedia browsing could download it, if they wanted it. This is the description Alex gave: "To recap we would be producing a mediawiki plugin for version x (and above preferably) which, for your test pages, would automatically extract chemical names (and other chemical file types) from text and annotate the text with dotted red underline and add an image (via tooltip) of the extracted structure. Unlike here, there would be no chemical table of contents across the top and the URL would not have "...chemicalize.org..." in it and would be the same as before."

They have been working on the design, and they are now at the point where they need our input. Their specific questions are:

1. How many pages do we need to be covering (just chembox pages or all wikipedia or a test site of 'n' pages)?
2. What's the frequency of edits (ie we want to know how many pages we need to process daily)?
3. What functionality of chemicalize is wanted (just adding images to chem names, storing structures to allow chem search, providing chem search interface...?
4. What's the med/long term future (it's fine to make a toy but if we make for production it's a different approach)?

Please could you give your feedback below. Also, I will set up an IRC meeting with Alex Allerdyce for (hopefully) next week for people to ask more about it. I think that if we provide input, they could provide us with a really useful tool (for example, chemical searches?), but if we don't explain what we want, it will be of limited value. So, please advise! Walkerma (talk) 15:28, 24 June 2011 (UTC)

Since we don't have any comments, I'm thinking we should hold off until the first week of July, which is better for Alex Allerdyce. Walkerma (talk) 13:03, 28 June 2011 (UTC)

DOT hazard symbols

Hi Chemists!

I corresponded with the DOT and verified that all of their hazard symbols are public domain. There are about 40 of them. Wonder if there is someone interested in uploading them? See [13]. TCO (talk) 00:19, 29 June 2011 (UTC)

P.s. I used the 4 signs for F transport in the F article and it came out very nice as a graphic to illustrate precautions. There is some other document that says what is required when. (Note, not advocating "how to" on transport. Just describing some aspects of usage, one of which is here.)TCO (talk) 01:05, 29 June 2011 (UTC)

Drug versus chem box

A discussion is taking place here. [14] Doc James (talk · contribs · email) 17:33, 29 June 2011 (UTC)

Template:Chemformula

{{Chemformula}} has been nominated for deletion. 65.94.47.63 (talk) 04:54, 30 June 2011 (UTC)

4-Methylbenzoic acid move

For the sake of consistency with o-Toluic acid and m-Toluic acid, and per WP:COMMONNAME, can someone move 4-Methylbenzoic acid to p-Toluic acid? It seems to require an administrator to do this, because the title exists as a rediect. Thanks. ChemNerd (talk) 20:14, 4 July 2011 (UTC)

 Done -- Ed (Edgar181) 21:24, 4 July 2011 (UTC)

Titanium dioxide

Banned Aoganov (talk · contribs) is back on Mohs hardness and titanium dioxide, where he is launching a new controversy between himself and his old nemesis Dubrovinskaia. I don't see any secondary sources or notability of said controversy, and thus reverting his edits, and get reverted back, thus someone please have a look (at titanium dioxide foremost) to resolve edit warring. Materialscientist (talk) 14:09, 11 July 2011 (UTC)

Semiprotected for two weeks. Vsmith (talk) 15:55, 11 July 2011 (UTC)

Reliable source?

Should the student-generated data found at an open source notebook be used as a source of data in the infoboxes for our chemical articles? (example for benzoic acid used as a source for non-aqueous solubility at benzoic acid) My conclusion is that it does not meet Wikipedia's criteria outlined at WP:RS. I brought this up before, a couple of years ago (archived here) and data from this source was removed. But it seems that student supporters of that project have reintroduced the data. I think it would be good to establish a firm consensus about whether to use this data or not, so I have started a discussion at Wikipedia:Reliable_sources/Noticeboard#Student-generated_open_notebook_data - please contribute to the discussion there. ChemNerd (talk) 18:17, 12 July 2011 (UTC)

2,5-Furandicarboxylic acid

2,5-Furandicarboxylic acid's not been reassesed in over two years, but has grown more than 11k bytes since. It seems to me it should rank as B-/High. --Belg4mit (talk) 04:53, 14 July 2011 (UTC)

Going by Wikipedia:WikiProject_Chemicals/Assessment#Importance_scale, I'd say a low or mid at the most. The article speculates about possibilities, but I don't see it used in volumes like sulfuric acid. --Rifleman 82 (talk) 16:05, 14 July 2011 (UTC)

I'm not a regular contributor to the project, so I might be wrong, but I don't interpret those criteria as being based on volume of chemical produced. The chemical seems like a significant intermediary with other (possible) uses, and the article to be trher well fleshed out. --Belg4mit (talk) 21:29, 14 July 2011 (UTC)

Going by the stated guidelines, an encyclopedia would be lacking if it did not have an article on sulfuric acid or sodium hydroxide, but if it did not have an article on a relatively obscure compound like this one, it's not unacceptable. Both scales are independent of each other. Some of our best articles are on scientific curiosities like rhodocene, for example, which is low in importance, but FA in quality. Perhaps a rather specialized topic is easier to master than a broader one. --Rifleman 82 (talk) 22:11, 14 July 2011 (UTC)

Commons:Commons talk:WikiProject Chemistry/Categories#Plurals and derivatives

Some other opinions on how to categorize on Commons would be good. --Leyo 21:54, 14 July 2011 (UTC)

Nobody, really? --Leyo 19:24, 22 July 2011 (UTC)

Element 0

I would like to have it expanded. Plasmic Physics (talk) 06:52, 16 July 2011 (UTC)

Have a look on the discussion page of Element 0 and here at Neutron#Stability_and_beta_decay and Neutron#Neutron_compounds. Cheers, Shinkolobwe (talk) 23:40, 17 July 2011 (UTC)

Former discussion about tetraneutron

A very similar topic has already been discussed previously elsewhere: Talk:Tetraneutron. See, amongst others in the discussion on this talk page, the chemical point of view debated for the unproved concept of Tetraneutron, never confirmed and only suggested via one single empiric test that could never be reproduced. Shinkolobwe (talk) 00:08, 18 July 2011 (UTC)

Amine hydrofluorides or ammonium fluorides?

File:Olaflur2.png and File:Dectaflur.png show alkylated ammonium fluorides, while PubChem ([15], [16]) says they are amine hydrofluorides, i.e. the N is not protonated. While I generally don't trust PubChem too much, they may be right here, seeing that the alkylated amines should be pretty weak bases. Any ideas what the preferred form should be? Thanks, ἀνυπόδητος (talk) 08:11, 23 July 2011 (UTC)

MSDS

A lot (quick search suggests 191) of MSDS appear to come from jtbaker.com - since this company appears to have changed, the links to the MSDS no longer work (eg triphenylphosphine. I suggest removing all the links from infoboxes' MSDS sections to jtbaker.com. It may be sensible to replace them with a link to the appropriate hazard.com search, eg PPh3, rather than a specific MSDS. I'm unsure of the details, but presumably a check of these searches and selection of a more appropriate link if necessary may be incorporated into the infobox validation? Any thoughts? I imagine this would be trivially achievable via AWB and am happy to give it a go. Martinp23 15:19, 23 July 2011 (UTC)

Also, 237 articles had MSDS hosted at ilo.org, which were broken links (going to the ilo.org homepage). They're fairly easy to fix, and I have done so (bot request for approval). Martinp23 16:33, 23 July 2011 (UTC)

hazard.com also appears to mirror old jtbaker.com MSDS (eg, PPh3). So, the links could be updated to point to these instead, which has the benefit of going direct to the MSDS (and if they disappear from there at some point in the future, the idea above (of pointing to a hazard.com msds search) is still valid)). How do people feel? Martinp23 17:06, 23 July 2011 (UTC)

We can't really validate the content from the MSDSs, but we could certainly try to validate the fact that there is a valid link. The problem is that (as you've shown) with any external website you can have pages moved or deleted. Is there a bot that can detect such dead links? Could we do this periodically with our MSDS links? I agree that the hazard.com option sounds good, though we don't want to be seen to be favouring one specific site overwhelmingly; also, what if hazard.com decides to move their URLs around! Still, that doesn't mean I'm opposed to your proposal, which seems sound. Walkerma (talk) 19:23, 25 July 2011 (UTC)

I'm unsure if there's an existing bot that can monitor for link changes (though I agree it'd be great to have) - the difficulty of course is detecting what is a "broken link", since for both jtbaker and ilo.org, the old MSDS links caused the user to be redirected to the company homepage. If a bot were to look for this sort of redirection, it could probably work. Or, just load the suggested MSDS link and if some common MSDS phrase isn't found there (eg, the name of the chemical or any of its synonyms), mark the link for review. On hazard.com - the nice thing seems to be that they link to various companies' MSDS, so we aren't necessarily (eg) favouring any given company's MSDS - and the reader can view a wide selection. Martinp23 21:58, 25 July 2011 (UTC)

Melting & boiling point validation

I'm proposing that we finally have a go at this, because we have an opportunity to work with a group who are looking at melting point validation in general. I've written up my thoughts here, and invited the group to join us on IRC on Thursday, July 28th at 1500h UTC (11am US EDT) on #wikichem. Please join us for the IRC, even if you don't plan to work on the validation effort, because we need to get the input of the Wikipedia chemistry community. Thanks! Walkerma (talk) 19:27, 25 July 2011 (UTC)

Article move request

Would any administrator out there be so kind as to move octathiocane to cyclooctasulfur? --Ben (talk) 15:31, 26 July 2011 (UTC)

How about octasulfur? That's how NIST lists it, and it sounds simpler. GHits for octasulfur and cyclooctasulfur are ~ 3k, octathiocane ~ 1.4k.--Rifleman 82 (talk) 16:20, 26 July 2011 (UTC)

Yeah, either of those are fine. Does anyone else have a preference? Just not octathiocane – it's a silly name for reasons I explain at Talk:Octathiocane. --Ben (talk) 17:38, 26 July 2011 (UTC)

Thank you very much for the move. Would you mind doing the same for S₆: Hexathiane → Hexasulfur? --Ben (talk) 17:59, 30 July 2011 (UTC)

Hydrogen astatide

A user is repeatingly removing referenced systematic names, without a willingness to discuss, or an apparent understanding of systematic naming. Requesting mediation? Note, this user has a recent history of disrutive edits. Plasmic Physics (talk) 23:36, 26 July 2011 (UTC)

3-Methyl-2-butanol

Someone put a warning up at the top of this page that some information is incorrect. I don't have the time to sort it out, so if anyone wishes to look into it, that would be great. Regards, P. D. Cook ^{Talk to me!} 19:51, 4 August 2011 (UTC)

Should be fixed. --Rifleman 82 (talk) 23:39, 4 August 2011 (UTC)

Thanks for taking care of that. P. D. Cook ^{Talk to me!} 12:24, 5 August 2011 (UTC)

Chembox updated also. Plasmic Physics (talk) 13:03, 5 August 2011 (UTC)

Edit war at Hydrogen astatide

This edit war at Hydrogen astatide has gone on long enough. Both User:Plasmic Physics and User:Fivexthethird should stop reverting each other. I count at least twelve reversions, a ridiculous number considering the three revert rule. Plasmic Physics has initiated a discussion at Talk:Hydrogen astatide.

On the matter in question, the IUPAC Red Book 2005 specifically mentions HAt in Table IX on page 298. It says:

HAt, hydrogen astatide

[HAt], astatidohydrogen

According to the explanatory text preceding the table, the latter name is used to refer specifically to molecular HAt (is there any other kind of HAt?).

In my opinion, acrimonious disputes over nomenclature reflect badly on Wikipedia. I get the feeling this dispute is less about finding the correct IUPAC name for an obscure compound and more about editors throwing their weight around, seeking some sort of dominance or ownership of a little piece of the internet. --Ben (talk) 12:58, 7 August 2011 (UTC)

It is a failure of the WikiProject to not intervene when issue was first raised, and to only respond as a result of escalation. Plasmic Physics (talk) 14:03, 7 August 2011 (UTC)

Really? Couldn't you have just discussed it with Fivexthethird earlier? Why is it always someone else's fault? --Ben (talk) 15:17, 7 August 2011 (UTC)

An early Wikipedian coming to the realisation that dead horses can't be made to go anywhere.

I have removed the whole field. Get to a consensus first on the talkpage, and then let an independent editor add the consensus value back. I will warn both editors that this edit warring is not the way forward, and that further edit warring will result in (possibly lengthy) blocks. If you disagree, either leave it at a wrong version for some time and discuss it, or even just remove it while discussing it. There is no excuse for edit warring, ever.

And Plasmic Physics, don't blame it on other editors, we are all just volunteers here, we do not have a deadline, and consider, that sometimes you should drop the stick and slowly back away - there will be other things you can do, this nomenclature issue is not going to be solved overnight (if ever), and note, it is not a question of references there. --Dirk Beetstra ^{T C} 15:47, 7 August 2011 (UTC)

Users warned: diff and diff. --Dirk Beetstra ^{T C} 15:55, 7 August 2011 (UTC)

I did not blame anyone, I just called it as I saw it. I was of the persuation that the project was supposed to handle chemistry related issues, my mistake. Plasmic Physics (talk) 12:08, 10 August 2011 (UTC)

Yes, the project is supposed to handle chemistry related issues, but if that is not happening (we are all just volunteers), then that is not a reason to edit war about it. --Dirk Beetstra ^{T C} 12:16, 10 August 2011 (UTC)

OK, maybe an edit war wasn't the best idea. I don't know whether not a single project participant had the time to have a look at the issue, or whether just no one could be bothered until it turned into an edit war. Plasmic Physics (talk) 12:40, 10 August 2011 (UTC)

Does it matter whether someone else had time to look at it, or whether someone else actually bothered? Neither is a reason to get into an edit war about it. --Dirk Beetstra ^{T C} 12:45, 10 August 2011 (UTC)

Is agreeing not enough? Yes, it does matter whether no one had the time, or whether no one could care. Plasmic Physics (talk) 12:55, 10 August 2011 (UTC)

Dihydrophenylisatin

I'm having trouble verifying the new article dihydrophenylisatin. The chemical name does not appear in SciFinder, ChemSpider, Reaxys, PubMed, or PubChem. Web searches only turn up non-authoritative sites mentioning it as a constituent of prunes. Is this something that someone just made up and then it got spread around the internet? Or is it a misspelling (or uncommon synonym) of a real chemical compound? Any ideas, chemists? -- Ed (Edgar181) 11:56, 10 August 2011 (UTC)

It is mentioned in this paper (used as a reference in prune), but there's no indication of chemical identity. -- Ed (Edgar181) 12:04, 10 August 2011 (UTC)

Isatin and 1-phenylisatin are both compounds where there is chemical information on, this seems to be related to that, though 'dihydro-1-phenylisatin' does not yield any results - where are the two 'hydro's'? Is the phenyl really on '1'? --Dirk Beetstra ^{T C} 12:12, 10 August 2011 (UTC)

When in doubt, substitution is usually at position 1. Plasmic Physics (talk) 12:42, 10 August 2011 (UTC)

A systematic name for 1-phenylisatin is 1-phenyl-2,3-dihydro-1H-indole-2,3-d, maybe dihydrophenylisatin is just a chimera of the two names. Plasmic Physics (talk) 12:58, 10 August 2011 (UTC)

OK, here is more that I have turned up. The terms "dihydroxyphenylisatin" and "dihydroxyphenyl isatin" also show up in the popular literature in connection with prunes. But I can't find these terms in the scientific literature except in a couple of really old (>50 years) articles and they seem to be referring to dihydroxydiphenylisatin, a synthetic laxative more commonly known as oxyphenisatine. I don't think this compound is found in prunes though. This review article, PMID 11401245, on the chemical composition of prunes does not mention dihydrophenylisatin, dihydroxyphenylisatin, or dihydroxydiphenylisatin. This all makes me think that the synthetic laxative drug somehow got mistakenly connected with prunes (and mistakenly spelled) in the popular press. -- Ed (Edgar181) 13:20, 10 August 2011 (UTC)

Thanks for your help! There's a reason I switched to engineering classes after the first chemistry class in college, so I don't have much to offer on this discussion other than some additional lay searches. Maybe I got something useful? [17] analyzes prunes and says, "A quantitative estimation for dihenyl isatins was devised using di(acetylhydroxyphenyl)isatin." [18] found di(acetylhydroxyphenyl)isatin to be a stimulant and laxative in rats. -- ke4roh (talk) 13:46, 10 August 2011 (UTC)

Di(acetylhydroxyphenyl)isatin is a synthetic derivative of oxyphenisatine. It looks like the 1951 paper identified something that might be an isatin derivative similar to oxyphenisatine, but they do not definitively identify it. Analytical techniques were probably insufficient for the task at the time.

I'd be inclined to redirect dihydrophenylisatin to oxyphenisatine at this point. Any objections? -- Ed (Edgar181) 14:34, 10 August 2011 (UTC)

I'm still confused. Oxyphenisatine causes liver damage (per its article) and I haven't heard of liver damage from prunes (not that I would know, but a quick search also turned up nothing). It seems to me that dihydrophenylisatin might be best described as "a lay term for the stimulant laxative component(s) of prunes composed of [and here is my confusion]". In that case, it ceases to be a chemical article, but links to one or more chemical articles. Wiktionary should also be updated accordingly. -- ke4roh (talk) 16:01, 10 August 2011 (UTC)

I don't think prunes really contain dihydrophenylisatin/oxyphenisatine. As far as I can tell, there is no primary scientific literature (including the two papers you linked) to support that conclusion. Studies that have examined the chemical constituents in prunes do not mention dihydrophenylisatin/oxyphenisatine. There may be some evidence from the older literature (like the 1951 paper you link) to suggest chemical compounds similar to dihydrophenylisatin/oxyphenisatine are in prunes, and it seems to me that there is a misconception in the lay press about this. If Wikipedia is to include a comment that "dihydrophenylisatin" is a lay term for the stimulant laxative component(s) of prunes, I think that would be best placed in oxyphenisatine, with a redirect from dihydrophenylisatin. -- Ed (Edgar181) 17:07, 10 August 2011 (UTC)

I'll go for that. I'd do it, but I don't know how to word the link between oxyphenisatine and prunes. -- ke4roh (talk) 18:45, 10 August 2011 (UTC)

OK, I updated oxyphenisatine and redirected dihydrophenylisatin. Let me know what you think of my wording. -- Ed (Edgar181) 19:11, 10 August 2011 (UTC)

That works and doesn't cloud the issue with trying to talk about some random lay term. Thanks again. -- ke4roh (talk) 16:32, 11 August 2011 (UTC)

acids, names and more

(sorry, is going to be tl;dr; but the issue continues and continues)

Yesterday I noticed a couple of edits by Plasmic Physics on Hydrochloric acid (double diff), Hydrofluoric acid (diff) and Hydrobromic acid (diff). In all three the edit summary mentions that the data removed by Plasmic Physics is pertaining to resp. Hydrogen chloride, Hydrogen fluoride and Hydrogen bromide.

Looking at the diffs, e.g. for Hydrobromic acid, Plasmic Physics removed:

• ChemSpiderID = 255 - following the link to the ChemSpider site leads to HBr, it seems to be a mixed record between Hydrogen bromide and Hydrobromic acid - record is named 'hydrogen bromide', but the 'Wikipedia articles' section shows both, searching for 'hydrobromic acid' only finds hydrogen bromide. ChemSpider does not make a difference between the free molecule and hydrobromic acid (note: they should have different identifiers for both, but that is not the issue)
• CASNo = 10035-10-6 - the record obtained is for a mixed record for hydrogen bromide and hydrobromic acid - the name commonchemistry gives to the record is 'hydrobromic acid' (note: they should have different identifiers for both, but that is not the issue)
• Appearance = colorless liquid - well, it is a colorless liquid
• MeltingPt = -11 °C (47-49% w/w aq.) - yep, if you cool it down, the 47-49% solution will solidify at approx. -11 °C
• BoilingPt = 122 °C at 700 mmHg (47-49% w/w aq.) - yes, you can distill this stuff, the 47-49% solution will distill at 122°C/700 mmHg. You don't separate it into HBr and H₂O at that point.
• Density = 1.49 g/cm3 (48% w/w aq.) - yes, the 48% solution has a density of 1.49 kg/L.
• ExternalMSDS = ICSC 0282 - this is the MSDS of hydrobromic acid, the liquid, albeit maybe of one specific concentration, but it is of hydrobromic acid, not hydrogen bromide.

For all three diffs the changes are similar. The reasoning Plasmic Physics is giving here, is that this is not a 'pure' compound - properties are (generally) pertaining to one specific concentration (but for most fields, that is given - the appearance does not notably change with changing concentration, the MSDS may be more specific, vide infra).

Most of these fields are not incorrect (I am willing to entertain the idea that hydrobromic acid has a different InChI than hydrogen bromide, though I am not that familiar with that part of the concept of it - what would be the InChI of 48% w/w hydrogen bromide in water?).

To me, a lot of this information should be in the article, there is importance in the effect of concentration on some of the properties, for some enough to discuss them in the text. For Plasmic Physics that seems to be a reason to consider the removal of most of the chembox (even advocating the whole removal, it is not a 'pure chemical' so it should not have a chembox). I argue, that the chembox here should contain some key data, I believe that it is important for example that an interested reader opens Hydrobromic acid, and sees from the chembox that the liquid has a distinct boiling point at 48% w/w. That triggers the 'oh, you can distill this'. Of course, the user of the data may want to distill a 40% solution, and that is not in the page, but seeing that you can distill a 48% solution gives already the information that it may be possible to distill a 40% solution as well (and the article should later on then elaborate on that, what happens when you distill the different concentrations). Also the identifiers, of course, it would be great if they lead perfectly to the right compound and the right data (but of course, it may link to 48% while you are looking for the 40% solution - but the point is, that it leads to information on hydrobromic acid, maybe not the perfect concentration that you are looking for, but the identifier will bring you closer to it. If Wikipedia does not help you there, and the commonchemistry.com site does not help you there, then at least the CAS-number will snowball you to information on HBr, it will take you more work to find the correct article, but it is more than that you first will also have to find the CAS before you can do the CAS search - and we all know that searching SciFinder on 'HBr' will leave you to such an excessive amount of data, that filtering that is going to be even more difficult). Having the perfect identifier there for your compound is great and the best utility, but sometimes the second best is a good editorial choice (and there are more reasons why having those identifiers there is a good thing, not just as a link out for us chemistry-nerds needing information on hydrobromic acid), something that helps you on the way, more than a complete dismissal of all that info.

After reverting these edits, I contacted Plasmic Physics on his talkpage (User_talk:Plasmic_Physics#Hydrofluoric acid / Hydrobromic acid), where I found out that a) Plasmic Physics removed this before (see e.g. diff), and b) it was discussed before (see Wikipedia talk:WikiProject Chemicals/Archive 2011#Hydrogen chloride vs. Hydrochloric acid). (note, I have reincorporated the safety section as well, which was removed in said edit, the MSDS referred to is the MSDS of hydrochloric acid, albeit of unknown concentration there).

I can't but help thinking of all the other cases, just above here is Hydrogen astatide, where Plasmic Physics was edit warring with someone else about the systematic naming, and earlier there was a case with hydrates of salts (where all the hydrates were incorporated in the chembox with all their identifiers - now thinking of it, that is excessive, vide infra).

Suggested use of chembox:

• The chembox is to show key information about a substance. When that is of a typical solution, choose one or two typical concentrations and give data for that, when it is hydrates, chose the common ones. The rest of the data goes either into the text (e.g. in tables, with explanation) or into a supplementary data page. Some of the data is of importance to the (class of) compound(s), other information will help you towards the information that you are looking for on external sites. Omitting that info is bad for the usefulness of the page, having too much as well. Choose a middle way, and if in doubt, all our content pages have a talkpage, or we have a project here, discuss and wait for consensus (and if that does not develop, do something else).

Plasmic Physics, please remember who you are writing for. Seen that so many parts of the chembox where you are editing result in extensive discussions here, maybe you should consider to step away from the chembox completely (and maybe also from the drugbox) for some time (except for uncontroversial typo-fixing and vandalism reverts), and use your skills on the content of the pages (of course, you can post perceived significant problems on talkpages or here). I know you have the best intentions, but you run over and over into disagreements with other editors over these things, and I am sorry, but even if you are right, these changes are not uncontroversial, and they do need significant discussion before being applied (and when such discussions don't come to a conclusion, then leave the status quo, and maybe revisit it again in due time). --Dirk Beetstra ^{T C} 10:07, 11 August 2011 (UTC)

Another reference for related comments: Talk:Hydrochloric acid. Plasmic Physics (talk) 11:02, 11 August 2011 (UTC)

Deleting Template:[Element] compounds

Remember the debate we had earlier this year? Well, it's time for action. Please join discussions at Wikipedia:Templates for discussion/Log/2011 July 26. There exists a link to our earlier debate, for reference. Plasmic Physics (talk) 23:12, 26 July 2011 (UTC)

It has now been relisted on Wikipedia:Templates for discussion/Log/2011 August 16.

BTW: There are currently several chemical structures for deletion. --Leyo 07:02, 16 August 2011 (UTC)

Y(III)

Hello! I just wanted to ask why many elements that have a predominant oxidation state (for example, +3 for yttrium), but their compounds articles are named like yttrium(III) chloride instead of yttrium chloride? There's some rule on Wikipedia to use this nomenclature only when it's confusing (for example, iron(II) and iron(III) are OK). Thanks--R8R Gtrs (talk) 11:51, 4 September 2011 (UTC)

There is no particular reason, probably the result of well-intentioned application of nomenclature rules by editors that dont actually use these things. Speaking for myself, yttrium(III) oxide is not as good as Yttrium oxide, which is what it is called by inorganic chemists and by commercial sources. If you get some feedback here, then we might change the names around. We, for example, do not call many aluminium compounds aluminium(III) ...--Smokefoot (talk) 13:23, 4 September 2011 (UTC)

Good suggestion: Indeed, in the absence of any ambiguity, the best option is likely to chose the simplest name carrying all the relevant information and avoiding complicating the chemical names without reason. "You know you have achieved perfection in writing (or designing) not when you have nothing more to add, but when you have nothing more to take aways" (Antoine de Saint Exupery). A supplementary advantage is also to avoid useless redirect links and to facilitate and to speed-up the search on the Wikipedia servers. Shinkolobwe (talk) 16:45, 4 September 2011 (UTC)

Here is a list of compound names that need migrating from name(III) ... to name ...:

Scandium(III) chloride, Scandium(III) fluoride, Scandium(III) nitrate, Scandium(III) oxide, Scandium(III) sulfide, Scandium(III) trifluoromethanesulfonate, Yttrium(III) chloride, Yttrium(III) oxide, Yttrium(III) fluoride, Yttrium(III) bromide, Yttrium(III) sulfide, Yttrium(III) antimonide, Yttrium(III) arsenide, Lanthanum(III) chloride, Lanthanum(III) bromide, Praseodymium(III) chloride, Praseodymium(III) oxide, Praseodymium(III) sulfide, Neodymium(III) chloride, Neodymium(III) oxide, Gadolinium(III) chloride, Terbium(III) bromide, Terbium(III) chloride, Terbium(III) iodide, Terbium(III) oxide, Dysprosium(III) chloride, Dysprosium(III) oxide, Holmium(III) chloride, Holmium(III) oxide, Erbium(III) chloride, Thulium(III) chloride, Thulium(III) oxide, Ytterbium(II) chloride, Ytterbium(III) bromide, Ytterbium(III) chloride, Ytterbium(III) fluoride, Ytterbium(III) oxide, Lutetium(III) chloride, Lutetium(III) oxide. For some of these elements, divalent or other weird derivatives have been identified but these compounds are, I think, cleanly trivalent. --Smokefoot (talk) 12:27, 6 September 2011 (UTC)

To clarify, these are suggested for mass moving from xxxum(III) yyyide to xxxum yyyide. Thus please shout if there objections and add what is missing. Materialscientist (talk) 12:39, 6 September 2011 (UTC)

There is Yb in the list (what's more, both YbCl3 and YbCl2). Also, why not promethium(III) oxide?--R8R Gtrs (talk) 14:20, 6 September 2011 (UTC)

Good points: promethium(III) oxide should be on the list. Apparently not YbCl₃. It also turns out that many of the diiodides have been made in recent years --Smokefoot (talk) 02:03, 8 September 2011 (UTC)

Dioxane

Our intermittent but determined colleague User:MotherAmy is keen to highlight the occurrence of dioxane in cosmetics and related soapy items containing products of ethoxylation (reaction with ethylene oxide), two big ingredients being sodium myreth sulfate and sodium laureth sulfate. Whether the dioxane is in the commerical products as a consequence of product degradation or imperfect ethoxylation, I dont know. But apparently several reports point to the potential health risks with the traces of dioxane. In my opinion, the health concerns merit noting, but not worth highlighting or even dominating these articles (the gist of WP:UNDUE). But I am sure that upon her return, User:MotherAmy will see things quite differently. So by this message, I am giving notice of a likely struggle where the intervention of administrators will likely be required. --Smokefoot (talk) 02:03, 8 September 2011 (UTC)

Recommended Section

Would be great if each compound page could contain instructions or pointers on how to make that compound safe for disposition, or a note why it cannot be made safe. Instructions should be oriented to laymen so that it is accessible to everyone that wants to be a good citizen and not just toss it in the bin. — Preceding unsigned comment added by 66.32.212.126 (talk) 15:18, 13 September 2011 (UTC)

help please

Suberic acid told me that he's sad. — Preceding unsigned comment added by 70.189.170.229 (talk) 13:52, 14 September 2011 (UTC)

Palau’amine

Palau’amine contains a character which is not on my keyboard. Is this a common ’ - or should we move the article to the Palau'amine, which uses the more common ' ?? --Dirk Beetstra ^{T C} 10:06, 16 September 2011 (UTC)

Here is a linguistically sound answer: WT:LANG#Palau’amine. --ἀνυπόδητος (talk) 18:45, 16 September 2011 (UTC)

I created a redirect at the ASCII-apostrophe form, since that's what's easy to type (useful for people searching by name) and is how it's included in databases that don't use fancy characters (pubchem, etc.). Feel free to move the actual page to that location (with redirect from others based on typography, etc.) if that's more "correct". DMacks (talk) 19:39, 16 September 2011 (UTC)

I swapped the redirect and the article. To me it seems that the cited references also use the <'>, and not the <’>. Redirect from the original name is still there. --Dirk Beetstra ^{T C} 08:48, 19 September 2011 (UTC)

Tempo 20 wp

I have some discomfort with this new article about an insecticide, which popped up on my radar screen for reasons that are not important. Chemicals are way outside my domain of knowledge, so I'm just going to raise a flag here and feel that I have done my duty. Looie496 (talk) 19:07, 16 September 2011 (UTC)

Yes, that article is on some of our radars also. Rather than focus specifically on Tempo 20 wp, we are discussing this new editing style above. We need to wait to see if we achieve some consensus before deciding what to do.--Smokefoot (talk) 23:40, 16 September 2011 (UTC)

Dextro- and Levoamphetamine

Our pages for dextroamphetamine and levoamphetamine currently list the same IUPAC name, (2S)-1-phenylpropan-2-amine, which should be corrected. I don't know which the correct one is. I'm also not sure if the structure pictures shown on the two articles are correct. AxelBoldt (talk) 18:51, 18 September 2011 (UTC)

Fixed stereochemistry. Thanks for spotting this! I'm not 100% sure whether the space filling models are the right way round; could you check whether they match the skeletal formulae? --ἀνυπόδητος (talk) 19:17, 18 September 2011 (UTC)

Thanks for the quick fix. I have a hard time reading stereochemistry if the hydrogens aren't show, but I believe these two pages show different stereochemistries for dextroamphetamine:

• http://webbook.nist.gov/cgi/cbook.cgi?ID=C51649
• http://www.commonchemistry.org/ChemicalDetail.aspx?ref=51-64-9

The second one seems to agree with our structure File:D-amphetamine.svg and I assume it is the correct one? AxelBoldt (talk) 20:05, 18 September 2011 (UTC)

Yes, the NIST page shows correct "other names" with (S)-..., but the structure drawing is (R), which is actually levoamphetamine. --ἀνυπόδητος (talk) 08:19, 19 September 2011 (UTC)

I'm fairly sure that the space filling model matches the stereoscopy of . AxelBoldt (talk) 23:29, 18 September 2011 (UTC)

Recommend New Template or Project

Strongly recommend a non-academic template or project for topics like the following regarding chemicals, chemistry, pesticides, insecticides, fungicide, adhesives, lubricants, petroleum, minerals, mining, pharmaceuticals, ....

• Safety Risks
• Disposal
• Hazard lists
• Hazard Communication
• Right to Know
• Transportation
• Labeling Requirements
• Worker Protection
• Regulation
• Registration
• Licensing
• Emergencies
• Injury
• Medical Treatment
• Insurance
• Government agencies
• International organizations
• Working groups

There appears to be an intellectual vacuum and an overall lack of structure for non-academic topics that would concern the average reader. Just about every chemical substance article needs to provide access to non-academic information needed by people that lack a college or university degree covering related topics. I hope this finds everyone well. Best regards,Nanoatzin (talk) 07:51, 14 September 2011 (UTC)

I guess it depends on what one defines as an "intellectual vacuum". I think Wikipedia-Chem does a pretty good job describing chemicals and how they work in everyday life. The scope is challenging because chemistry is inherently difficult to non-experts. Our overall philosophy, in effect, is that chemical knowledge is the path to safe handing of chemicals but is no substitute for expert medical knowledge. Thus, I do not think that the above template would satisfy the mission followed by most editors here, which is to explain chemistry, and not to serve as an "advice column." We carefully refer to MSDS sites, which are more authoritative than we can hope to be (WP:NOTMANUAL).. By doing so, we send the message that Wikipedia is not the place to get advice on solving medical problems (or how to do homework or build a chemical plant). In some extreme case, we have fairly extended discussions of toxicology and environmental risks, and in these cases we tend not to enforce the usual rules of reliable sources. I am looking forward to a healthy discussion on this topic.--Smokefoot (talk) 10:33, 14 September 2011 (UTC)

What Smokefoot says is similar to what I think about it. I agree that some of this information should be in articles, but we have to take care in which way it is represented. Medical Treatment, as an example, is something that needs much care and should not sound like advice, and that should be referenced properly. Worker Protection may soon get too much like a manual - and it is not Wikipedia's task on that - it is saver to say that, e.g., that the compound is toxic (hence, work out some toxicology, what does it physically do in your body) and that it penetrates the skin readily (and why does it do that). We then don't say 'where thick rubber gloves when handling this compound. I do see that that automatically results in the text being technical and difficult to grasp for most outside of the field (though it should be our goal to write why it penetrates the skin in a simple and clear way that everyone can understand - e.g. skin has a fatty protecting layer on it, fatty compounds are hydrophobic, and this compound readily mixes with hydrophobic substances, making it easy to penetrate that layer and get into contact with the cells). For the rest, Wikipedia should just link to one or two authoritative sources for the more specialistic info, like MSDS or medical (or similar) databases. Have the why's available, have the physical data there, and have direct external links to the information that is there of importance. --Dirk Beetstra ^{T C} 10:49, 14 September 2011 (UTC)

I concur with Dirk Beetstra on this. Also you will find that some of the requested topics are local to each country, and so it will become verbose to give a description of every government's regulations on a chemical. I there is enough material on the topic then we can have an article on chemicals by country, eg ammonium nitrate in Brazil. There is likely to be enough published material to write such articles, but I am unenthused about people spending time writing them! Graeme Bartlett (talk) 12:13, 14 September 2011 (UTC)

The existing template was written with a logical thought process in mind: What is it? How do you make it? What can you do with it? These are the most important topics to discuss in any article on a chemical - do you disagree?

Wikipedia is not a safety manual, and Wikipedia is unable to serve as an authoritative source, nor should it try. It is a general reference and a starting point to further reading. Our existing approach has been to give a brief mention of safety in the infobox. Here, the reader can get an idea of the compound at a glance using some recognized standards (R/S phrases or the new GHS, NFPA, etc.) An MSDS is usually linked; this gives much more comprehensive information which manufacturers are required to provide (and which vary by country). Unless a hazard is particularly notable, there should be no mention in the text because repetitive statements to the effect "use PPE" say nothing, really, and is clutter more than useful information.

Your proposed skeleton for articles seems to encourage advocacy, something which seems to conflict with WP:NPOV. I strongly disagree with this move. --Rifleman 82 (talk) 03:44, 15 September 2011 (UTC)

My personal opinion is that creating an additional "non-academic template" for articles on chemicals is unnecessary. The {{chembox}} template is already quite thorough and content that is suitable for the article, but does not fit in the current version of the infobox can be added to the article text. -- Ed (Edgar181) 19:19, 16 September 2011 (UTC)

I revised our MOS to reflect the consensus in the above. I also tried to make the MOS more straightforward..--Smokefoot (talk) 17:18, 30 September 2011 (UTC)

Merging drugbox into chembox: take 2

A request for comment has been made at the above link. Your input is welcome. Boghog (talk) 03:12, 26 September 2011 (UTC)

Scarlet GN

I am a bit confused here: According to ChemIDplus (search for “Scarlet GN”) the structure (position of one SO₃ group) and the CAS RN are different. Could someone check this? --Leyo 21:42, 25 September 2011 (UTC)

Nothing in Ullmann's Encyclopedia's article on azo dyes on Scarlet GN or the RN that you found. There are zillions of these things though. --Smokefoot (talk) 22:51, 25 September 2011 (UTC)

I searched SciFinder for “Scarlet GN”:

Registry Number: 3257-28-1

CA Index Name: 1-Naphthalenesulfonic acid, 6-[2-(2,4-dimethyl-6-sulfophenyl)diazenyl]-5-hydroxy-, sodium salt (1:2)

Other Names: 1-Naphthalenesulfonic acid, 6-[(2,4-dimethyl-6-sulfophenyl)azo]-5-hydroxy-, disodium salt (9CI); C.I. Food Red 2 (7CI); C.I. Food Red 2, disodium salt (8CI); Scarlet GN Specially Pure (6CI); Acid Scarlet GNA; Acid Scarlet JN Extra Pure A; C.I. 14815; Cilefa Red G; E 125; E 125 (dye); Eurocert Scarlet GN; Food Red 2; Food Red No. 2; L Red Z 3000; Salmon Red Geigy; Scarlet GN

Hence, our article incl. structure is on a different compound. Should we correct the article or move it to what it currently describes? --Leyo 13:12, 26 September 2011 (UTC)

The name "Scarlet GN" is more important than the structure diagram or systematic name; we should fix these, and if someone thinks the other compound is notable they can make that — Preceding unsigned comment added by 70.189.170.229 (talk) 22:27, 29 September 2011 (UTC)

I verified the structure of this compound. Conclusion: the image given in the article is a correct minor tautomer of the tautomer distrabution, it apears to be the canonical structure. Plasmic Physics (talk) 04:52, 1 October 2011 (UTC)

• 
  Scarlet GN (3257-28-1)
• 
  C.I. Food Red 1 (4548-53-2)

Are you sure about that? The CAS RN and the structure in the article seem to fit, but not the name. --Leyo 10:28, 1 October 2011 (UTC)

I just did a double check, and switched out the data. Plasmic Physics (talk) 13:50, 1 October 2011 (UTC)

Merger of copper(II) sulfate pentahydrate into copper(II) sulfate?

There is a discussion at Talk:Copper(II) sulfate on my proposal to merge copper(II) sulfate pentahydrate into copper(II) sulfate, where the various hydrated and anhydrous forms would be summarized. This deliberation would have implications for hundreds of articles since many transition metal salts exist in diverse solvates (not just hydrates) as well as unsolvated forms, not to mention various polymorphs of each. We welcome input, as usual.--Smokefoot (talk) 02:46, 5 October 2011 (UTC)

Article request for mercapto radical

Would someone please create the article mercapto radical (HS)? I saw it in this news story.[19] Thanks. Jesanj (talk) 19:04, 8 October 2011 (UTC)

• I have started a stub. Graeme Bartlett (talk) 22:17, 8 October 2011 (UTC)

Mercapto radical propagates a misnomer, I fear. This article will confuse professional chemists, because I suspect that most chemists define mercaptan as an organic thiol, where radicals of the type RS. are common. Atmospheric scientists are probably not the group to get advice about nomenclature, their amazing work notwithstanding. --Smokefoot (talk) 22:58, 8 October 2011 (UTC)

Well what is the correct name for this radical then? Should it be Sulfanyl radical The idea was to write about .SH not about the organic radicals, they already have their own functional group page at thiols. Graeme Bartlett (talk) 02:11, 9 October 2011 (UTC)

Article-name for Eu(fod)₃

It's currently at Eufod, and the article originally used the term (but not the article-title) "EuFOD". Now the article says the standard names are "Eufod", "Eu(fod)", and "Eu(fod)3". I've usually seen it EuFOD (is what Aldrich calls it) or Eu(fod)₃ and never with just the first letter capitalized. I'm thinking it should be renamed, wondering what others think is the correct place. DMacks (talk) 04:23, 19 October 2011 (UTC)

Just move it, and leave the redirect. --Dirk Beetstra ^{T C} 08:09, 19 October 2011 (UTC)

I agree. Just pick the standard name that seems to be used most often (EuFOD is my guess) and move it there. It would be best to make all uses of the word match the title too - the article currently switches between variants. -- Ed (Edgar181) 11:53, 19 October 2011 (UTC)

Androstenol

Please check, either the image, or the identifiers are incorrect. The PubChem link is for Androst-16-en-3-ol, is it the same thing? Plasmic Physics (talk) 07:08, 26 October 2011 (UTC)

I think there is just a missing 'H' in the image .. did not notice that when I verified the stuff. All verified identifiers are for the one without the methyl (and that seems also to be for the pubchem, ánd the systematic name). Good catch, PP. --Dirk Beetstra ^{T C} 10:31, 31 October 2011 (UTC)

Infobox validation for Uric Acid

The infobox for Uric acid is showing a red cross next to the KEGG reference, but this value is correct. What should I do, if anything, to correct this? Many thanks, Niall Jackson (talk) 23:29, 31 October 2011 (UTC)

Nothing, that I know of. Everytime I corrected the template entry, a bot reverted it, so I just stopped trying. Eventually, the bot corrects it on its own, it just takes a while. Plasmic Physics (talk) 00:15, 1 November 2011 (UTC)

Lesquerolic acid

Would someone who knows what they're doing please have a look at lesquerolic acid, which I've just created? I'm sure that it needs a chembox, but I haven't a clue how to make one. Thanks. Waitak (talk) 22:40, 15 November 2011 (UTC)

Thanks to User:Rifleman 82 for turning lesquerolic acid into a proper article. Waitak (talk) 04:18, 16 November 2011 (UTC)

Conversation ratios of salts for cocaine?

Like the nested table of the ones for morphine on its page, does anybody have a list of salts as such for cocaine with conversation ratios? I notice the crack cocaine article immediate cites a rather wide spread but dubious assertion that it is "the most addictive form" of cocaine (it has any number of easily found citations for such, we need to find one against, that in effect this is more due to the RoA, and is not even the most addictive RoA: IV is moreso, which *requires* it to be a salt). Seeing as the article is essentially the freebase article for the substance, such a list might clarify the lack of innate difference to the substance. 66.243.226.11 (talk) 11:39, 17 November 2011 (UTC)

Morphine metabolite page made

Morphine-N-oxide could someone help out with an info box & information? At least so its similar to the M3G/M6G articles linked therein? Thanks 216.227.116.61 (talk) 06:08, 16 November 2011 (UTC)

I added a chembox and some data. -- Ed (Edgar181) 12:39, 16 November 2011 (UTC)

Thanks, it's looking acceptable now. 66.243.226.11 (talk) 11:33, 17 November 2011 (UTC)

Anyone care to do the same for the new pseudomorphine article? 66.243.226.11 (talk) 09:14, 18 November 2011 (UTC)

Done. Does your chemisty drawing software support some graphics format that is more suitable than GIF? PNG or SVG would result in a better image. --ἀνυπόδητος (talk) 14:06, 19 November 2011 (UTC)

(I've been grabbing them from elsewhere due to the PD-chem free copyright mostly.) I also can't seem to find any analgesic information on it, could anyone else? That would be the last informational facet I'm seeking for pseudomorphine. 66.243.226.11 (talk) 21:10, 20 November 2011 (UTC)

Psilocybin

Hi, I've added this group's WikiProject tag to the above article. I'm planning to take the article to FAC soon, and would highly appreciate it if anybody could have a look at the Chemistry section to see if it meets your expectations of what an FA article should contain. Thanks, Sasata (talk) 17:04, 21 November 2011 (UTC)

Tropane-esque molcules.

I had a few questions, could anybody give me a synopsis of how these chemicals come about, and if they're natural tropane alkaloids?:

[(1R,2S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-yl] 2,2-diphenyl-2-pheny lmethoxy-acetate hydrochloride CAS: 87421-58-7

&

[(1R,2R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-yl] 3,4,5-trimethoxybenzoate CAS: 87421-59-8

Are they anything like Truxillines? (e.g. alkaloids that are UV-driven dimerization products of cinnamoylcocaines in Erythroxylum species)?

I am trying to add as many metabolite & analogue structures of cocaine (and related tropanes) to Wikipedia as I can. Nagelfar (talk) 14:19, 23 November 2011 (UTC)

IUPAC for 7-Hydroxymitragynine

7-Hydroxymitragynine has "7-Hydroxymitragynine" in its info box as it's IUPAC name. This is clearly wrong, but a google search just yields a whole lot of sites referencing that as its IUPAC as well. Perhaps the Mitragynine article could help (being related). Could someone please find the true IUPAC of 7HO-M? 216.227.117.69 (talk) 16:37, 23 November 2011 (UTC)

What about this? --Leyo 17:18, 23 November 2011 (UTC)

Ball-and-stick or space-filling?

A few months ago, I uploaded a lot of molecule pictures to Commons, and I haven't yet started the task of inserting them into articles here at en.Wikipedia. In most cases I uploaded both a ball-and-stick model and a space-filling model. In some cases the ball-and-stick model might be better, and in other cases the space-filling model might be more appropriate. In some cases it might be a good idea to show both. So it would be nice to have a semi-official guideline on which one to use, in the interest of consistency. Please leave your suggestions. Ephemeronium (talk) 13:35, 19 November 2011 (UTC)

I will write some guidelines that of course could be edited by others. Here are some views:

• ChemDraw-like images should be the default for most molecular compounds. They convey connectivity, identify atoms explicitly, and are easily understood.
• Ball-and-stick are seductive because they look hi-tech and students love producing them. Such images are helpful in providing an impression of the shape of a molecule. These drawings remind readers just how "hydrogen-coated" most organic molecules are. Drawback is that few people understand which atoms go where for non-hydrocarbons. Some programs show multiple bonds in a really dorky way, for my tastes. These images must be used judiciously for many metal containing compounds where the bonding can be complicated, e.g., metal carbonyls.
• Space filling is closest to the "truth" but are correspondingly difficult to understand and usually convey little insight. Space-filling images should be used selectively to make a point (e.g. the buried nature of host-guest species such as ionophores). Here is an example where the space-filling is effective:

The structure of the complex of sodium (Na⁺) and the antibiotic monensin-A.

Well those are one editor's views. --Smokefoot (talk) 16:29, 19 November 2011 (UTC)

I vote for both. Plasmic Physics (talk) 08:10, 20 November 2011 (UTC)

I agree. If we have high quality ball-and-stick images and high quality space-filling images would should generally include them both. But I don't think we need any kind of rule - there is room for editorial decision making. For very complex molecules, space-filling models may simply not be able to convey much because useful information can get buried - but they can be extremely useful in cases such as Smokefoot's host-guest example. -- Ed (Edgar181) 14:18, 21 November 2011 (UTC)

I would most certainly not standard go for 'both', but selectively. Smokefoot's example is a good one, that shows the point of the host-guest complex. But on many others, they either don't convey any information, or the information is less .. true than what is depicted. A fully stretched eicosane ball-and-stick is fine (though already a bit unrealistic), a fully stretched eicosane as space filling image .. well, that may be true in a perfect crystal but that is about it, and probably far from realistic of how it normally is. I would use it all with common sense, and when the ball-and-stick starts to obscure itself (so you would need 3-4 different viewing angles to view all) already consider not to add it, and same for space-filling - it may then be better to use one or two in the text where there is explanation of a feature. --Dirk Beetstra ^{T C} 14:29, 21 November 2011 (UTC)

Entire structure shown, looks good, no problem.

Thanks for your input, guys. I myself admit I am a sucker for ball-and-stick models, and use them whenever possible. This, partly because I feel they are more intuitive to the non-chemist. One niche that space-filling models might have better is for planar molecules, such as CS gas, but more often I'd prefer a ball-and-stick model. But this is also partly for aesthetic reasons. I ask of you, when should aesthetics be considered? Aesthetics and information don't have to be mutually exclusive. An easy to understand depiction of a molecule is a thing of beauty in itself, and often the best images are the ones that look good. Ephemeronium (talk) 18:27, 26 November 2011 (UTC)

Chemical structure mass deletion

Wikipedia:Files for deletion/2011_November_27#All_files_in_category_Unclassified_Chemical_Structures might interest some of you. I haven't really made sense of it myself. On the one hand, some people seem to be saying that these are all low-quality images for which better ones exist, and on the other hand, someone is talking about how he'll eventually create high-quality versions of them. WhatamIdoing (talk) 22:31, 28 November 2011 (UTC)

Blacklisting http://www.guidechem.com/

• Proposal: blacklist this site
• Reason: recent mass addition here; user warned, then another one comes in. Edits are either adding external link or copy/pasting the (copyrighted) site content [20]. It is a Chinese site which cites no references, but offers buying chemicals as much as possible. Materialscientist (talk) 04:04, 29 November 2011 (UTC)

• Agree that these links are spam, but I suggest waiting a few days to see if warnings or blocks of these new editors will do anything. If other steps don't work, spam is a good enough reason to ask for a checkuser. New items on the blacklist add overhead on page saves. EdJohnston (talk) 04:17, 29 November 2011 (UTC)

  It's not about those two users (Rifleman 82 blocked them both anyway), this site was innocently used before, even by regulars [21], and the filter will alert us not to do so. Materialscientist (talk) 06:51, 29 November 2011 (UTC)

• If this is done just add it to the spam blacklist, and not an edit filter. Graeme Bartlett (talk) 10:37, 7 December 2011 (UTC)

  One more: Shalalawudi (talk · contribs). Materialscientist (talk) 04:14, 27 December 2011 (UTC)

Nomination for deletion of Template:Chembox subst explosive

Template:Chembox subst explosive has been nominated for deletion. You are invited to comment on the discussion at the template's entry on the Templates for discussion page. 76.65.128.198 (talk) 07:01, 10 December 2011 (UTC)