Wikipedia talk:WikiProject Chemistry/Archive 18

Water fluoridation featured-article restart

The Featured Article nomination of Water fluoridation (edit | talk | history | protect | delete | links | watch | logs | views) has been restarted. Previous comments have been archived, so we now have a fresh start. Further comments are welcome on the nomination page. Eubulides (talk) 07:00, 1 March 2009 (UTC)

Request for help from WP:MEASURE

I've been doing some article assessment at WikiProject Measurement recently and I came across the article Apothecaries' system (not one of mine) which seems pretty good. For the time being, I've rated it as A-class on our project quality scale, but I would welcome further comments so I have opened a peer review here. If there are editors with any knowledge or interest in the subject, I'd be grateful if they could read through the article and tell us if there is anything important which should be in there but which isn't at the moment. Cheers! Physchim62 (talk) 11:21, 1 March 2009 (UTC)

List of important publications in chemistry

Could we please have a few more eyes looking at Talk:List of important publications in chemistry#New organic chemistry entry. In particular how do we alter the "Description" and "Importance" sections, if we follow User:Walkerma's advice and keep this entry. Recently we tightened the inclusion criteria and there was a discussion on the talk page about removing some entries, although the discussion was only between User:Dirac66 and myself. It would be good to have more comment on that, particularly on entries on organic chemistry books, although discussion on any entry is welcome. We also of course want many more good entries to this list. --Bduke (Discussion) 03:39, 2 March 2009 (UTC)

Plumbide

I started an article about Plumbide and was told to come here for help expanding it. Chlorine Trifluoride (talk) 17:08, 4 March 2009 (UTC)

I can echo the comments made by DMacks on Talk:Plumbide. What the article needs quite urgently is some idea of why these compounds are special. You define plumbides as "chemical compounds that contain lead in an anionic form", but is the lead really anionic? Physchim62 (talk) 17:19, 4 March 2009 (UTC)

I've given a few refs and a summary of Greenwood & Earnshaw at Talk:Plumbide. Polyplumbide anions are apparently interesting and important.

Ben (talk) 19:55, 4 March 2009 (UTC)

I added all of the info that I could find about lead anions from the source, although I may have missed some of it. I also noticed that there were some useful diagrams of the anion structure. How could we add those to the article? Chlorine Trifluoride (talk) 00:46, 7 March 2009 (UTC)

List of Radioactive Elements

List of Radioactive Elements has been nominated for deletion. 76.66.201.179 (talk) 04:54, 10 March 2009 (UTC)

Article Sorting

I noticed that Chemistry articles can be sorted by importance and by class. What about both? Chlorine Trifluoride (talk) 15:11, 10 March 2009 (UTC)

If you look at a complete list, all parameters can be used to "sort by", simply by clicking on the column header. We had a complete list as of August on the toolserver, for Version 0.7, but that got deleted recently for some reason. But I'll be asking CBM to do another bot run for 1.0 soon, and then you'll have exactly what you want. Walkerma (talk) 15:56, 10 March 2009 (UTC)

The only list that I found was the one called "Daily Status Report". Where is the complete list? Chlorine Trifluoride (talk) 16:18, 10 March 2009 (UTC)

Deletion of wrong or poor structures

There is an ongoing discussion on the Commons about the deletion process for tagged wrong or poor structures. Your input would be welcome on Commons:Administrators' noticeboard#Superseding. Cacycle (talk) 14:15, 13 March 2009 (UTC)

Article alerts

This is a notice to let you know about Article alerts, a fully-automated subscription-based news delivery system designed to notify WikiProjects and Taskforces when articles are entering Articles for deletion, Requests for comment, Peer review and other workflows (full list). The reports are updated on a daily basis, and provide brief summaries of what happened, with relevant links to discussion or results when possible. A certain degree of customization is available; WikiProjects and Taskforces can choose which workflows to include, have individual reports generated for each workflow, have deletion discussion transcluded on the reports, and so on. An example of a customized report can be found here.

If you are already subscribed to Article Alerts, it is now easier to report bugs and request new features. We are also in the process of implementing a "news system", which would let projects know about ongoing discussions on a wikipedia-wide level, and other things of interest. The developers also note that some subscribing WikiProjects and Taskforces use the display=none parameter, but forget to give a link to their alert page. Your alert page should be located at "Wikipedia:PROJECT-OR-TASKFORCE-HOMEPAGE/Article alerts". Questions and feedback should be left at Wikipedia talk:Article alerts.

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Thanks. — Headbomb {^ταλκ_{κοντριβς} – WP Physics} 08:56, 15 March, 2009 (UTC)

Amino acids - how to depict - and references for images

Hi everyone, I recently made a new image for glycine which reminded me that the way we depict amino acids and other potentially zwitterionic species probably needs to be discussed and put in the MoS.

Here's my reasoning for glycine: Talk:Glycine#Structure. Is this best discussed at Wikipedia talk:Manual of Style (chemistry)?

A while ago, I started including references in my 3D images, and now I'm at the stage where I am very reluctant to upload a 3D model of a species unless its precise 3D structure has been determined experimentally (or sometimes computationally, but this is not ideal in the absence of experimental verification).

There's still a great deal of value in 3D images that correctly match the 2D structure (right connectivity and stereochemistry), but that are not actually experimentally determined - crystal structures or spectroscopic measurements are sometimes hard to come by, difficult to make a model from, and there's often little disadvantage in having an approximate structure in an article. Things can go wrong when conformation (or other trickery, e.g. zwitterion fun, as in arsanilic acid) is important, but the uploader doesn't know about it (I had this problem a lot in the past, before I had good access to journals).

I think we should really encourage reliably-sourced structures where possible - references on the image description page make it much easier to resolve the frequent complaints of "wrong structure", many of which are unfounded accusations! Even if the reference isn't particularly reliable, the uploader should indicate where they got the information from - even if it's just from them own knowledge.

Ben (talk) 13:44, 17 March 2009 (UTC)

• I completely agree with you on image sourcing. It is included in Wikipedia:Manual of Style (chemistry)/References and external links as an encouraged use of primary sources: perhaps you might like to make that even stronger? I'm afraid I don't have an easy answer for the zwitterion problem, but I'm sure others will have their opinions ;) Physchim62 (talk) 14:13, 17 March 2009 (UTC)

We *did* agree some indeterminate time ago, that we'd avoid zwitterionic forms in favor of uncharged species, but obviously if crystal structures are involved, it won't work. Agree with Ben that it's not a simple matter of placing a + on a N, and a - on a carboxylate. --Rifleman 82 (talk) 15:22, 17 March 2009 (UTC)

I do not see a value in using crystal structures for 3D structures of small molecules. Crystal structures do neither represent solution structures nor active conformations in case of bioactive compounds. The only case where crystal structures of small molecules make sense to me are substances that are used because of their crystal properties. It would make much more sense to use a global minimum energy conformation (perhaps taking into account information about active/binding conformations). Cacycle (talk) 16:34, 17 March 2009 (UTC)

Crystal structures of small molecules are valuable for making 3D structure images because they are easy to get hold of and easy to convert to a picture.

Global energy minimum conformations are not always easily available, and are not always accurate - they're not experimental data and can be a poor representation of the true conformation if the computational method used does not model reality accurately enough - how can you know your computed structure is right? Crystal structure data is more often available in an accessible format (pre-made into a CIF) whereas for computed or spectroscopically determined structures, you usually have to fix loads of bond lengths and angles - very time consuming and error prone for anything larger than a few atoms.

For bioactive compounds, it's good to have both the structure of the pure substance (crystal, microwave, IR) or its solution structure (NMR), AND the structure of the molecule interacting with its target (usually a drug fitting into an enzyme). The crystal structures of drugs in pure form are important and do influence their pharmacology - hence the desire for crystal structure prediction: Acta Cryst. (2009). B65, 107-125.

One thing we should not do is avoid the problem by saying "crystal structures don't necessarily correspond to solution structures" and therefore "let's use computations or NMR". This would be fine in an ideal world for some articles, but actually getting hold of a mistake-free computed or NMR structure is really hard and would in practice lead to loads of unillustrated articles. Computational articles should give PDBs, not just lists of cartesian coordinates to type in! For other articles, the crystal structure is the best representation - if the substance is most commonly encountered as a solid or its chemistry depends mostly on the crystal structure.

Uncharged amino acids seem to be found only in the gas phase - and that's what you'd get from a computation. Glycine is most commonly encountered in solution or crystal, where it's a zwitterion. Its crystal structure is important. Its zwitterionic nature makes it a much higher-melting solid than if it were uncharged, and glycine and similar molecules are widely used in crystal engineering. In its most important role as a part of proteins, it's not even an amino acid, it's a residue with amide groups. So maybe a picture of glycine bonded to the rest of a protein should be prominent.

Ben (talk) 19:14, 17 March 2009 (UTC)

The crystal structures of a compound are just one arbitrary conformation that is neither the dominant one in the gase phase, in solution, nor in its biological context (e.g. interacting with a protein). Actually, most small organic molecules in solution or the gas phase are so extremely flexible that you cannot even talk about a predominant species. We have the 3D structures here merely as an extension to the 2D structures to show how these translate into the third dimension. There is no didactic or encyclopedic reason to single out crystal structures for this purpose (and crystallographers and computational chemists do not rely on Wikipedia images for crystal structures). In my opinion, we should use energy minimized structures that are close to the global gas phase minimum and are either in a biologically or didactically (i.e. easy to overview) relevant conformation. Oh, I am only talking about small organic molecules, for (partially) inorganic compounds and complexes crystal structures are much more relevant. As for zwitterions and other reversibly charged compounds I agree that in general we should use the uncharged structures for didactic reasons in 2D as well as 3D to keep it simple. Cacycle (talk) 22:25, 17 March 2009 (UTC)

The crystal structure of a compound might be the dominant conformation in gas or solution, but you're right that you can't automatically assume so. Molecules may be flexible, but a 3D structure is very important in my opinion, since 2D structures are hard to understand if you're not a chemist. "No didactic or encyclopedic reason to single out crystal structures" - no, but there are pragmatic reasons - they're available and easy to make into images, and are usually better than no image. Skeletal formulae can be misleading w.r.t molecular shape, e.g. morphine. For very small molecules, I do tend to use microwave spectroscopy to show the gas-phase structure.

I can do uncharged 3D structures of zwitterions, but I think it's a bad idea to take the crystal structure of a zwitterion and just move a proton - other bond angles and lengths can change when protons move. For glycine, I've been tracking down gas-phase structure determinations - but there are several conformers.

It's a troublesome issue. We need 3D images - they're far better for novices, and they show important stereochemical features properly. But it's hard to know which structure to use. I'm not going to start running everything through Spartan, because it won't necessarily give the global energy minimum, and freaks out with phosphorus, sulfur etc. And it's original research.

Ben (talk) 22:42, 17 March 2009 (UTC)

Not easy. As I read it, Ben's point is that we have to choose a structure, and it's better to pick the one derived from a crystal structure rather than a random one based on how ChemDraw generated it - that makes sense. Cacycle is right, of course, that the situation in solution is very different; but we always have to simplify, otherwise we couldn't have a structure at all for a complex solution structure like this. I think Ben's solution at least makes the choice for us, and it bears at least a semblance to reality in one phase of the substance.

Regarding the zwitterionic form, that is tricky too. There is the issue of structural accuracy vs clarity of representation. For example, we mostly draw benzene with three double bonds, for clarity of representation, even though we know that it is (taken by itself) a completely incorrect representation of the true stucture. With the amino acids, I think (I may be wrong) on IRC we decided to keep things simple and show them in un-ionised forms, but that is because of (a) simplicity and (b) tradition. Perhaps we should look at how most books represent amino acids, but the textbooks I've seen (probably not representative!) usually use the "neutral" forms in the lists and tables, then have a section explaining the zwitterionic structure separately. As Wikipedia becomes structure-searchable (we're moving in that direction), the "clarity" issue becomes more significant. If you were doing a structure search for an unusual amino acid, how would YOU draw it? I'm not saying that zwitterions are wrong - I could be convinced that they are the best choice - I'm only pointing out that it's not simply a problem of structural accuracy. Sorry for muddying the waters even more! Walkerma (talk) 04:08, 18 March 2009 (UTC)

I think you summarise the problem nicely, Martin. I'm not really trying to push zwitterions for amino acids, in fact I started this topic because I felt a little uneasy about replacing the pic at glycine. Considering the complexity of the structure situation with amino acids, and the importance of their structure, I think the topic should be discussed in detail with images of all the relevant forms in each amino acid article, or at least a brief discussion with images of the amino acid in question followed by a link to a more detailed discussion at Amino acid#Zwitterions or similar. Unless you know about zwitterionic amino acids, you're unlikely to find the information in Amino acid#Zwitterions from reading, say, glycine - the word "zwitterion" doesn't even appear in the article!

I think standard biochemistry texts use zwitterionic representations of amino acids - Voet and Stryer do.

Ben (talk) 08:44, 18 March 2009 (UTC)

3D view the good old fashioned way...

Regarding the 3D images: I see them as something similar to a molecular model kit image. We should make sure that there are no obvious conformational problems (especially with respect to anti/gauche conformations for linear chains, chair and equatorial conformations for saturated rings, in-plane conformations for conjugated systems, and use of energy-minimized strained ring systems). This is what I meant with "energy minimized structures that are close to the global gas phase minimum". I do not think that we necessarily need computational minimization (and quantum chemistry is certainly overkill...), but nowadays it is much faster to use energy minimization to relax a molecule than to adjust every single torsion angle by hand...

Regarding the charges: Every structure search engine should be able to automatically find protonation state variants. While for the chemboxes we should use the uncharged species, every article about zwitterions and other biochemicals that are charged at physiological conditions should elaborate on that, perhaps using additional structures for illustration. Cacycle (talk) 19:17, 18 March 2009 (UTC)

Chromium catalysts

The chromium pages gives the statement that one application of chromium is As a catalyst. I searched a little bit, and found countless applications of chromium compounds in oxidation reactions, but none mentioned the significance of the described process. If somebody knows a large scale application for chromium or a chromium compound as catalyst, it would help me a lot. The literature and the references are than easy to find. Thanks --Stone (talk) 17:39, 17 March 2009 (UTC)

Cp₂Cr on silica is/was used for polymerization of alkenes, the Theopold equation describes a proposed mechanism. Another catalyst for polymerization is Cr₂O₃ on alumina. I amnot sure how economically significant these catalyst systems are.--Axiosaurus (talk) 18:17, 17 March 2009 (UTC)

Thanks, I had the impression that chromium oxides are used for oxidation or reduction reactions because there are several possible intermediates on the way from Cr₂O₃ to CrO₃ and back. --Stone (talk) 20:02, 17 March 2009 (UTC)

The polymerisation looks also good. [Olefin polymerization over supported chromium oxide catalysts] Phillips-type catalysts will be my next look for industrial importance of chromium.--Stone (talk) 20:05, 17 March 2009 (UTC)

As described in Organochromium chemistry V8rik (talk) 21:02, 17 March 2009 (UTC)

Thanks!! I put it into the article. --Stone (talk) 20:21, 21 March 2009 (UTC)

The chemistry section needs a look from a native speaker, but I will also ask at the elements project.--Stone (talk) 20:21, 21 March 2009 (UTC)

Folic acid: aid needed

I'm trying to create a spoken version of folic acid. However, I've run into a problem; the equation in the Biochemistry of DNA base and amino acid production section seems, to me, to be nonsensical. I'm having difficulty determining waht it was actually supposed to be. If someone could take a look at it, I would be much obliged. Thanks! Sophus Bie ^(talk) 06:41, 20 March 2009 (UTC)

It's not nonsense, but simply a bit cryptic. I have elaborated it a bit, so that its meaning is more obvious now. If you want to pronounce the 'formula', you could say "Folate is reduced to dihydrofolate, which is then reduced to tetrahydrofolate. Adding carbon donors gives methylene-THF, which can be reduced to methyl-THF." If after this explanation, the whole symbolic, still cryptic line is still not contributing to the article, feel free to delete it altogether. You'd have my support for that. Wim van Dorst (talk) 18:46, 4 April 2009 (UTC).

Nobel Prize Laureates

I wanted to look at most of the chemistry Nobel Prize Laureates and found that most of them are not in the scope of the Chemistry project so I added them to our scope. The only problem I had was the importance scale, for my impression they should be Mid or High. Theodore William Richards was rated Top now I am wondering if we should make them all Top or all High? Any suggestions?--Stone (talk) 20:29, 21 March 2009 (UTC)

We certainly should make them all "High" and maybe even all "Top". Nobel winners have to be the most important biography articles we oversee. --Bduke (Discussion) 21:16, 21 March 2009 (UTC)

They shouldn't typically be "Top", because Top-importance is typically the most important 1% or so of the articles - which would total around 50-100 articles for chemistry (excluding chemicals). We will want to keep Top reserved for things like Acid, and the only chemists to get that distinction would (IMHO) be people like Lavoisier and Faraday. Walkerma (talk) 06:55, 22 March 2009 (UTC)

I agree, most Chemistry Nobel Laureates should be rated High on the importance scale. Some--like Linus Pauling--I would rate as Top. Shanata (talk) 07:22, 22 March 2009 (UTC)

I will try to get them, but I will make Liebig and Wöhler also Top,because I am afraid of the gost of Kolbe. --Stone (talk) 09:36, 22 March 2009 (UTC)

Esterification

Appreciate some ideas on what else should belong to this article. Tried to tidy it up with stuff off the top of my head (references pending!). I'll eventually get some stuff about the comparisions with amides, but I'm not sure what else to talk about. Ideas, please! --Rifleman 82 (talk) 14:33, 22 March 2009 (UTC)

• The DCC and DMAP method both done with the anhydrids for the synthesis of esters might be good with image wikimedia Esterification has some images which might be good. The first one would have the equilibrium arrows which should be in the first image.--Stone (talk) 15:38, 22 March 2009 (UTC)

Applications of matrices in chemistry?

I'm trying to write a GA on matrices. Are there any notable applications of matrices in chemistry? (I guess so...) Jakob.scholbach (talk) 17:08, 27 March 2009 (UTC)

I have added one example, but there is also the use of graph theory in chemistry. A chemical structure is a graph. See mathematical chemistry. --Bduke (Discussion) 21:07, 27 March 2009 (UTC)

You could say ALL of theoretical chemistry is about matrices, because, ultimately, it's all about eigenvectors and eigenvalues. Well, maybe not ALL all but at least all Ab initio quantum chemistry methods are essentially different ways of Fock matrix diagonalization. --Cubbi (talk) 03:52, 28 March 2009 (UTC)

To be pedantic, only Hartree-Fock calculations use Fock matrices, but matrices are used in post-HF methods like CI, MCSCF, MP2, CCSD, etc. --Bduke (Discussion) 07:21, 28 March 2009 (UTC)

Thanks for the infos. Would one of you volunteer to write a little section (5 lines or so) about that, perhaps with one or two enlightening examples, and also including references? Thanks again, Jakob.scholbach (talk) 10:59, 28 March 2009 (UTC)

New Taskforce

There is currently a new taskforce being setted up at WP:GLASS within the WikiProject Physics. It seems to me that it should at the same time also be within the WikiProject Chemistry, based on articles that are already within the WikiProject Chemistry such as Lead glass or Waterglass. Glass related categories of interest for chemists might be Glass types, Glass engineering and science, Common oxide glass components, or Glass in nature (e.g., corrosion behavior). Is there any opposition to adding a link to WP:GLASS on the WikiProject Chemistry page? Do you have other suggestion or ideas? You are very welcome to contribute. Thanks... --Afluegel (talk) 07:18, 28 March 2009 (UTC)

 Done I'm not sure there are any of our "regulars" who have specialist knowledge in the field – please speak up if I'm wrong! – but I'm sure we can help out if you point us in the right direction. I notice there's an article coming along on the glass transition, which some of our physical chemists might like to have a look at. Physchim62 (talk) 11:07, 28 March 2009 (UTC)

Thank you very much! Concerning the chemical side of glass (not to mention physical chemistry): In the main article glass there are still sections missing about glass corrosion, coatings (and possibly ion exchange) as described on the To-do list on the glass talk page. Glass corrosion is a purely chemical topic, but I am not sure if there is a specialised editor here. The corrosion is important for example for the beverage industry. Glass coatings are also a chemical topic, and we find the coatings now everywhere, for example heat-treatable IR-reflecting coatings based on thin Ag films in car windows. The heat treatable films are a challenge because during glass bending at several hundred degrees the Ag must not oxidize, and Na-ions must not migrate out of the glass into the films.--Afluegel (talk) 13:25, 29 March 2009 (UTC)

Poll on date autoformatting and linking

People may be interested to know that the Poll on date autoformatting and linking is now open. All users are invited to participate. Lightmouse (talk) 17:39, 31 March 2009 (UTC)

Spam issues?

People might comment on this: Blue Fuel , which looks like an advert. And then there is this link that showed up in a couple of articles:

• video and text explaining how AlBr3 is formed

Impressive video (at least to my eyes) but possibly spam or precursor to pay-to-view. --Smokefoot (talk) 12:24, 1 April 2009 (UTC)

Linking to video's is discouraged by several parts of the external links guideline (user contributed content, not always stable, not suitable for low-bandwidth users, not suitable for blind users, etc. etc.). I would say, revert and remove. In the same way fits liveleak.com (which is on Mercury(II) thiocyanate).

• liveleak.com: Linksearch en (insource) - meta - de - fr - simple - wikt:en - wikt:fr • Spamcheck • MER-C X-wiki • gs • Reports: Links on en - COIBot - COIBot-Local • Discussions: tracked - advanced - RSN • COIBot-Link, Local, & XWiki Reports - Wikipedia: en - fr - de • Google: search • meta • Domain: domaintools • AboutUs.com
• chem-toddler.com: Linksearch en (insource) - meta - de - fr - simple - wikt:en - wikt:fr • Spamcheck • MER-C X-wiki • gs • Reports: Links on en - COIBot - COIBot-Local • Discussions: tracked - advanced - RSN • COIBot-Link, Local, & XWiki Reports - Wikipedia: en - fr - de • Google: search • meta • Domain: domaintools • AboutUs.com

Chem-toddler seems a youtube rip or something similar. I am adding them both to XLinkBot, that should keep the floodgates a bit closed (though still in need of attention) while this discussion continues. --Dirk Beetstra ^{T C} 12:38, 1 April 2009 (UTC)

Horrendous article

Can someone please look at Selective chemistry of single-walled nanotubes? It is an utter piece of crap, and should probably be deleted. Just to give an idea, the article begins with "Reactivity of the fullerene molecules with respect to addition chemistries is strongly dependent on the curvature of the carbon framework. Their outer surface (exohedral) reactivity increases with increase in curvature." I cleaned it up a bit, but it still looks like a poorly written school paper, full of gaudy graphs and everything. Someone with more knowledge of the subject might be able to figure out what to do with it—whether that be to delete it or salvage it. I am not watching this project talk page, so the ball is now in your court. Good luck. — Twas Now ( talk • contribs • e-mail ) 04:05, 4 April 2009 (UTC)

• the article is not horrendous and no need for the crap either, the original author strikes me as competent in this field. Wiki needs more input from specialists in various fields and your comments are not exactly helping. Inexperienced editors often forget about the lead and make other beginners mistakes but experienced editors can help out. Agreed, the images uh detonate but for now they will have to do V8rik (talk) 17:49, 4 April 2009 (UTC)
• I guess my view is that the article is authored by ultra-narrow experts who lack perspective or are probably promoting their own specialized results. V8rik is correct however: the seeds of many good articles are planted by inexperienced gardeners.--Smokefoot (talk) 18:38, 4 April 2009 (UTC)
• I agree with V8rik. Actually, it would be nice to tell the author to write a page in simple english and post it on simple:. A box should be kept on the top saying that the article is in technical language, and the simple inglish version is at simple: —Preceding unsigned comment added by Manishearth (talk • contribs) 05:48, 14 April 2009 (UTC)

Chemical "layout" drawings

I'm wondering if anyone here would be able to identify these drawings so they can be properly labeled with descriptions and possibly converted to svg files and/or moved to commons:

• File:2C-B-FLY.gif
• File:2C-O-4.gif
• File:2C-O.gif
• File:2C-P.gif
• File:2C-T-2.gif
• File:2C-T-7.gif
• File:2C-T-9.gif
• File:2C-T.gif
• File:3164-85-01.gif

Thanks in advanced, Peachey88 ^{(Talk Page · Contribs)} 03:14, 11 April 2009 (UTC)

Most of them have been replaced by better versions (see 2C (psychedelics)) and could be deleted IMHO. The last one is potassium 2-ethylhexanoate and needs to be redrawn. --Leyo 18:26, 13 April 2009 (UTC)

 Done commons:File:Potassium 2-ethylhexanoate.png. Physchim62 (talk) 19:31, 13 April 2009 (UTC)

Thermoset polymer matrices

I believe this article (or, as it calls itself, "paper") is probably a student essay. It is in need of review from somebody with knowledge in the field. It lists some pretty questionable sources. It was up at the CP board, but I can't find any sign of infringement, neither through a search of selected phrases nor through a plagiarism checker. I also didn't see any duplicated text at those sources. Since this is far out of my field, I'm hoping somebody here will take it on. :) --Moonriddengirl ^(talk) 19:08, 14 April 2009 (UTC)

• It looks like it should be merged (possibly brutally merged) into thermosetting polymer. We're a little short on polymer experts here at the moment, so I'll give it a day to see if one turns up before I do anything more myself. Thanks for pointing it out to us, it will be dealt with! Physchim62 (talk) 00:39, 15 April 2009 (UTC)
  • Thanks much. If I tried to fix it myself, it wouldn't be pretty. :) --Moonriddengirl ^(talk) 00:43, 15 April 2009 (UTC)

Chem 538 - University of Michigan Class Project Part II

I updated this topic in Archive 17 but I also thought I would revive it on the current talk page to bring it to everyone's attention.

This class project is nearing its end for this semester and most of my students have posted their new/revised sites online. This term there was a lot more oversight and guidance provided to the students by myself and the graduate student instructor. We used group accounts again to simplify the grading but they will be terminated by the end of next week. Hopefully there will be less "wikifying" needed for each site. This was a graduate course in the "Organic Chemistry of Macromolecules" and overall I was impressed with the quality of their additions. I look forward to hearing your comments.

The topics this term were:

• Fire-safe polymers
• Shape Memory Polymers
• Gel permeation chromatography
• Anionic addition polymerization
• Step-growth polymerization
• Covalent organic framework

Please take a look and let me know if you have any suggestions/concerns/comments.Ajm mich (talk) 15:27, 15 April 2009 (UTC)

Niobium on the main page

All of us chemists should keep an eye on niobium today, since it's on the main page. Walkerma (talk) 03:44, 16 April 2009 (UTC)

Help with arrows

I am trying to update the chemical equation article with what it says here( chemical reaction equation - [[1]])in the gold book regarding the use of "=", "→" and two different double arrows for equilibrium and forward and backward reactions. Can we represent these different double arrows? There is a discussion here regarding the equilibrium symbol [2] but as they say in geordie land I was lost off by it! Was there a conclusion?

On a historical note when and why did the ability to document unbalanced reactions with "→", still taught here as I was taught, get lost? --Axiosaurus (talk) 10:48, 16 April 2009 (UTC)

For the equilibrium arrow, use {{eqm}}, which produces ⇌. I don't think the ability to document unbalanced equations has been lost at all: after all, not all chemical substances are stoichiometric! I guess there are some bloody pedants in the chemical education community who would like to insist that all equations are balanced, just as they insist on "ethanoic acid" for acetic acid, but they should be brutally ignored IMHO. Physchim62 (talk) 14:08, 16 April 2009 (UTC)

New cleanup template: {{Chemformula}}

Which can be used in sentences like:

Iron nitride{{chemformula}} may be super awesome, but buckminsterfullerenes{{chemformula}} are clearly even more awesome.

It populates Category:Articles needing chemical formulas.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 21:47, 16 April 2009 (UTC)

Feel free to tweak the text, and categories, etc... Headbomb {^ταλκ_{κοντριβς} – WP Physics} 21:55, 16 April 2009 (UTC)

OK... why would a compound need an inline mention of its chemical formula, particularly if the word is wikilinked? Am I missing something? Would this be used simply as a request to clarify ambiguous wording, such as "iron sulfate"? I can't see a need for "Diazepam{{chemformula}} is a benzodiazepine drug" or "Ethanol{{chemformula}} is widely used as a fuel in Brazil". Fvasconcellos (t·c) 00:29, 17 April 2009 (UTC)

I also do not support the use of this template. Although the idea is well-intentioned, the result would be annoying. Editors in the chem space are pretty good about appropriately explaining words with equations, and we would not be welcoming to (well-intentioned) bureaucrats stepping with tags. We are also pretty well self-policed and un-shy about correcting each other. Those are one editors's views at least.--Smokefoot (talk) 00:46, 17 April 2009 (UTC)

Well it's not something that would be used every time a compound is mentioned, but there are many times where it would be helpful to the reader to have the chemical formula. Not everyone is acquainted with IUPAC nomenclature, for example, when I read "iron nitride" all that immediately comes to mind is iron and some form of nitrogen. Is is FeN, FeN₄, FeNO₃, ... I don't immediately know. Now if I crunch a bit, I remember that it would have to mean something in the ballpark of Fe_xN_y. From the iron nitride article, it looks like it's Fe_xN. But in the iron nitride article, there is mention of ammonia. Now I know ammonia is NH₃, but that might not be obvious to a reader. If iron nitride is made explicit in that article, why not also make ammonia explicit? This would be especially useful if there isn't a wiki article for the compound, such as methyl hexenoate, etc... Now I agree its pretty ridiculous to explicit proteins and drugs (such as iboprufen{{chemformula}}) or even use it in articles with would mention say kerosen or ethanol where the chemical composition is pretty irrelevant. In the case of the iron nitride article though, you're talking about the breaking down of iron nitride into ammonia. This implies a certain reaction (something like Fe_xN + H₂0 → NH₃ + Fe₂O₃? [I didn't bother to balance things out or check if it makes sense, but you get the point]). Headbomb {^ταλκ_{κοντριβς} – WP Physics} 01:04, 17 April 2009 (UTC)

There are probably other less developed parts of Wikipedia that need your kind of help more than WE-Chem. The deal is that we (WE-Chem editors) do not aspire to make most articles accessible to novices. Articles on broad topics are reasonably accessible and improving steadily. The rate of improvement is not affected by tagging (that action is just annoying). Advanced articles should not be tagged because a beginner just shouldn't be there. Aspiring taggers risk being unable to distinguish advanced vs intro articles. Again, lest I convey anything but admiration for the gesture, the WE-chem community is sensitive to accessibility, and pays continuing (collaborative, consensus-driven, sometimes argumentative) attention to accessibility on the broader articles. --Smokefoot (talk) 03:55, 17 April 2009 (UTC)

I'd be annoyed if I kept seeing those tags everywhere. If wikilinked, why the need for tagging at all? You'll end up with nobody (but a few?) tagging, and nobody (but a few?) cleaning up. Net result is an eyesore. --Rifleman 82 (talk) 04:41, 17 April 2009 (UTC)

You can say that of any cleanup template. Why tag with {{fact}}, nobody but a few clean up? Why tag with {{copyedit}}? Nobody but a few clean up? This project seems to have a very cynical/elitist attitude, refusing to receive help in identifying problems from "lesser" people because of fear that a {{chemformula}} will be used where it shouldn't. Other templates are routinely used where they shouldn't, and they get removed when innapropriate. But suit yourselves. Headbomb {^ταλκ_{κοντριβς} – WP Physics} 04:55, 17 April 2009 (UTC)

I do not really understand why we need this template. There is no simple formula for buckminsterfullerene, it has a complex structure that is shown in the article. For iron nitride it would make much more sense to check the existing and already linked article and to add the formula (Fe_2-4N) yourself instead of placing that template. Am I missing something? Cacycle (talk) 14:17, 17 April 2009 (UTC)

The case of iron nitride is simple enough, but it also relies on the iron nitride page existing (which it didn't until two or three days ago). What about the case of Leucophosphite, a mineral (KFe₂[OH|(PO₄)₂]·2H₂O]) ([3]) or and unlinked phthalic acid (or mispelled phtalic acid) (C₆H₄(COOH)₂)?. At template is not to indicate that something cannot be improved if someone scours Wikipedia for a while, its to indicate that something can be improved. Anyway, it's there, so do what you want with it.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 15:13, 17 April 2009 (UTC)

Basketane and Germacrene

Can some nice person please draw better versions of the structures? Thanks, 69.157.194.162 (talk) 20:08, 18 April 2009 (UTC)

I'm working on it. Cacycle (talk)

Oops, I made pics for basketane, too - sorry, I had already done them when I saw you message.

Ben (talk) 23:44, 18 April 2009 (UTC)

Good, I have just finished germacrenes A - E :-) Cacycle (talk) 00:32, 19 April 2009 (UTC)

Richman Chemical

I declined the {{db-corp}} deletion on this one, because a quick Google search suggests notability, and in the hope that we can get a little help with the article. - Dan Dank55 (push to talk) 15:15, 23 April 2009 (UTC)

New articles

Some new articles will be reported here. Probably the submitting editors would welcome some help, especially on the geeky-formating stuff. Also of course, the science may be flawed. Another need will be to create redirects.

• 2-methylundecanal, Dimethyldichlorosilane (significant expansion), Amavadin, Chain shuttling polymerization, Phenylboronic acid, Cyclopentadienylcobalt dicarbonyl, Arsabenzene, Triphenylborane, Ethylenediaminedisuccinic acid, Niobium(IV) Chloride, Neophyl chloride, Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium, Methyltrichlorosilane (expansion), Pentamethylcyclopentadienyl Iridium Dichloride Dimer, Hexadecacarbonylhexarhodium, 1,2-difluorobenzene, Cis-Dichlorobis(ethylenediamine)cobalt(III) chloride, Pentachloronitrobenzene, Phthalonitrile, 2,2,4,4-tetramethyl-1,3-cyclobutanediol, Methyl isocyanide, Cyclopentadienyl allyl palladium, Difluorocarbene, Cyclopentadienyl thallium, Tetramethyl ammonium chloride, Dimethylphenylphosphine, Sodium tellurite (expansion), N-methylformamide, Tetrakis(acetonitrile)copper(I) hexafluorophosphate. (somewhere in the wiki-cosmos floats an article on Cr(C₆H₆)(CO)₃, but I can't find it). Again, I know that these articles are filled with problems, this series of messages are informational.

--Smokefoot (talk) 01:51, 24 April 2009 (UTC), updated May 6

Can we not abbreviate organic groups, please? Or if you're going to do it, at least mention that Ph is a benzene ring before you go slapping it in articles. shoy (reactions) 21:19, 29 April 2009 (UTC)

My apologies about the problems and flaws. Unfortunately, the glitches may get worse with each new article. With time, we can address these problems. (Ph as phenyl is the kind of detail these editors don't appreciate).--Smokefoot (talk) 04:30, 30 April 2009 (UTC)

I didn't mean to be combative about it. Sorry if it came across that way, I'll work on cleaning some of these articles up. shoy (reactions) 03:51, 4 May 2009 (UTC)

Just curious, is this a class project? Cacycle (talk) 16:02, 2 May 2009 (UTC)

Erythro etc

could someone tell me what these meso, erythro and theo mean in organic chemistry —Preceding unsigned comment added by 59.92.82.44 (talk) 17:30, 24 April 2009 (UTC)

See diastereomer.

Ben (talk) 17:56, 24 April 2009 (UTC)

Arrow-pushing

Can someone take a look at Arrow pushing, once you go past the lead, I can't see how the rest is connect to the subject, it just seems like a general description of a process? --Cameron Scott (talk) 19:51, 26 April 2009 (UTC)

Clayden

I've created a template for Organic Chemistry by Clayden et al since it is frequently cited in Wikipedia articles: {{Clayden}}.

I find myself using {{Greenwood&Earnshaw2nd}} all the time, so this new template should fulfil a similar role in organic articles.

Ben (talk) 14:20, 28 April 2009 (UTC)

Alkyl sulfonate

This article (Alkyl sulfonate) needs a hand, or should be merged with Sulfonic acid.--Stone (talk) 11:01, 2 May 2009 (UTC)

New college project

A college professor I know has a group of students working on improving articles. I provided him with some guidelines from User:Smokefoot and User:Proteins, who both have experience in this area, and I also advised him to look at WP:MOSCHEM. I think he's done quite a professional job with this

• Sigmatropic reaction - This is a significant upgrade of the previously existing page
• Frontier Molecular Orbital Theory - This is a new entry, and has been rated a C-class page already
• Electrocyclic reaction - This is a significant upgrade of the previously existing page
• Linoleic acid - This is a modest upgrade of a previously existing page
• Ribose-5-phosphate isomerase - Nice page written from scratch; late in the day they uncovered a stub on the same topic, Ribose isomerase.

Perhaps experienced wikichemists could keep an eye on these pages for problems, and be patient, though they look good so far - I see structure diagrams uploaded as Public Domain to the Commons using ACS settings and put in categories, that's a pretty good start in my book! Walkerma (talk) 23:05, 4 May 2009 (UTC)

• the existing Electrocyclic reaction page has simply been replaced with another one: outrageous. How is upgrade defined exactly V8rik (talk) 17:07, 5 May 2009 (UTC)

  I've reported this problem to the supervisor; he said they tried to incorporate the text, but found it very hard. I explained the system of building on what has gone before; they are going to restore some of the content, I believe, particularly some of the examples. Walkerma (talk) 21:48, 5 May 2009 (UTC)

gamma Boron

Hi, there is something happening at the boron aticle which needs a hand from more experienced admin or a editor, better familiar with the politics. Two groups discovered the new allotroph of boron and now one is accusing the other that he copied from his paper, because he got it previous to publication. This two groups are now plying a little bit with the boron article. Could we use some of the original research things on both groups to calm down the situatiuon? Thanks ---Stone (talk) 09:59, 9 May 2009 (UTC)

I agree, something needs to be done, it's getting impossible to read Talk:Boron because the discussion is so long and wordy.

User:Aoganov has been making some aggressive statements, demanding that User:NIMSoffice reveal their identity (I can't see anything at Wikipedia:Anonymity that requires users to identify themselves) and suggesting NIMSoffice be banned. However, both parties should read Wikipedia:Conflict of interest carefully and adhere to the guidelines there. It is important that Boron maintains a neutral POV and does not become the sole preserve of one or two editors.

I would like to see User:Aoganov and User:NIMSoffice voluntarily agree to leave Boron and Talk:Boron alone for a while and focus on other, less contentious articles. If the discussion on gamma-boron is to continue, it might be better for it to take place on a dedicated page (e.g. Talk:Boron/Gamma-boron) and for all contributors to stick to the encyclopaedic points in question and to be as concise as possible. Only when consensus is achieved should we update Boron.

I don't think the majority of people reading Boron are going to miss the discussion of γ-B for a short time until a satisfactory statement can be agreed upon.

We should also remind ourselves that personal attacks on other editors are forbidden and are a distraction from making a good encyclopaedia.

Ben (talk) 11:34, 9 May 2009 (UTC)

do not burden the boron page with these issues, move everything to a new article allotropes of boron (would make allotrope page number 7) ban both users from further editing (conflict of interest), wikipedia guidelines are a nightmare and most often useless in these matters (devise own rules) V8rik (talk) 21:06, 9 May 2009 (UTC)

The article on Gamma boron discovery controversy goes even further. I got the story from the other side of the controversy and this reads a lot different, making the view NPOV. We have to be careful to get this thing right. To accuse somebody of plagiarism and fraude is a big problem, if there is no credible source besides the word of the combatants.--Stone (talk) 05:01, 12 May 2009 (UTC)

Is this still an ongoing problem? It strikes me that Wikipedia is simply not the right place to air out the dispute. In fact, I feel that characterizing the dispute in here is boarderline WP:OR. It needs to be sorted out in a journal or equivalent before arrival on Wikipedia. Are there other perspectives about this out there? --HappyCamper 08:41, 14 May 2009 (UTC)

For those following along: Wikipedia:Administrators'_noticeboard/Incidents#request_for_a_correction. --HappyCamper 08:47, 14 May 2009 (UTC)

Started article on Allotropes of boron.--Stone (talk) 20:46, 20 May 2009 (UTC)

Gamma boron discovery controversy has been proposed for deletion: Wikipedia:Articles for deletion/Gamma boron discovery controversy. -Shootbamboo (talk) 21:48, 23 May 2009 (UTC)

ChemSpider acquired by RSC

Members of WP:Chemistry may be interested to hear that ChemSpider has been acquired by the Royal Society of Chemistry, as announced here. I think this will be helpful for our collaboration with ChemSpider. Walkerma (talk) 15:43, 11 May 2009 (UTC)

Keller's reagent

This stub article is currently nominated for deletion as it lacks sufficient context or sources. Searching for sources gives confusing results as there appears to be two different substances called Keller's reagent. The article and the AfD require input from an expert on the subject. McWomble (talk) 13:34, 16 May 2009 (UTC)

Nothing comes up on my searches for this reagent name. Shriner-Fuson-Curtin's qualitative organic book discusses the once well-known phenol-ferric test but does not call it by name, and a quick lit search shows no association between Keller and phenol. In a more perfect world, we'd have an article on qual organic (DNP, Lucas' reagent, Tollen's, etc).--Smokefoot (talk) 14:45, 16 May 2009 (UTC)

Have no access till monday, but doi:10.1002/hlca.19600430303--Stone (talk) 20:12, 16 May 2009 (UTC)

Pittcon Editors' Awards

I wonder if anybody could take a look at Pittcon Editors' Awards. I've copyedited it, but nothing links to it, so it's pretty hard to find. Any help would be appreciated! HJMitchell You rang? 07:00, 17 May 2009 (UTC)

Please make molecule drawings understandable to a wider public

Hi, I noticed that many molecular diagrams are being drawn following the convention that a carbon atom is implied at every unmarked corner, and with all (or most) hydrogens removed. See for example File:Methylcyclopropanesimp.png. While this "graphical slang" may be OK for complicated molecules, it is not at all friendly to a large segment of the readership (e.g. high-school students) who could understand and learn from molecular diagrams but are not used to this advanced convention. Please consider using complete diagrams whenever possibe. All the best, --Jorge Stolfi (talk) 22:10, 20 May 2009 (UTC)

Just be impressed that there even is an article on methylcyclopropane! This community is slowly replacing the "zen-like" images that you complain about, often showing multiple images. Overall pictures of small organic molecules will show all atom labels explicitly and larger molecules would use the graphical jargon. I think.--Smokefoot (talk) 00:26, 21 May 2009 (UTC)

Good point, although I think it is useful to have the skeletal formula there for readers who prefer it (they're often quicker to interpret for larger molecules).

Ben (talk) 12:49, 21 May 2009 (UTC)

I agree with all the above, although I don't think it would be a good idea to have full display of carbons and hydrogens for large and complex molecules that are only likely to be referred to by readers who understand the convention of skeletal formulae. For small, simple molecules, the sort which high-school students are likely to encounter, I think we need a variety of representations and we need to explain them clearly. Physchim62 (talk) 14:03, 21 May 2009 (UTC)

I agree completely with the above. One problem we have is that most people uploading structures are chemists, but many of our readers are students. If my college students struggle to get skeletal formulae right, what about the curious high school student? If we have a consensus on that, the questions we need to address are (a) where to draw the line between "simple" and "complicated" and (b) how best to draw non-skeletal formulae. Once we decide those things, we can put something into our MOS. Walkerma (talk) 16:26, 21 May 2009 (UTC)

I don't think we should "draw a line": My idea for a guideline would be "in case of doubt, try to include as many representations as are available and explain them.". Obviously the skeletal formula for methane is of no use to man nor beast, except perhaps as a full point, but when in comes to caffeine or limonene (two molecules that high-school students might encounter), the "line" is more blurred. Physchim62 (talk) 18:12, 21 May 2009 (UTC)

It is hard to draw a line, but some articles will obviously fall in one camp or the other, e.g. hexane.

For non-skeletal structures, which depiction is preferred?

1 2

3 4

5

There are are lot of drug articles out there that will primarily be of interest to non-scientists, but have skeletal formulae - this is a bit difficult, because the structures are often large and complicated, so explicit C and especially H is a problem (classic example is Atorvastatin).

My focus on 3D structures is partly for this reason - they're neater than structural formulas with all atoms explicit. The drawback is you have to know the colour scheme (although this can be guessed in conjunction with the skeletal formula) and some atoms get hidden behind others.

Ben (talk) 16:48, 21 May 2009 (UTC)

I like number 4 best, and I like 5 least. I agree that hexane is on the border and could go skeletal or explicit, but if we can fit two representations into the chembox it might be nice. Many things of course will always be too complicated to show explicit atoms. Thanks a lot, Ben! Walkerma (talk) 17:17, 21 May 2009 (UTC)

Wow, thanks to all for the prompt responses! As for the "beauty contest", I vote for 5, with 4 in second place. Reason: to show the geometry of the molecule in 3Dspace, the computer-graphicsy ball-and-sticks images are more effective than than 1 and 3. In any case, readers who care about the 3D geometry are probably experts, so the images should be chosen for them. The purpose of the 2D diagrams is to show the topology of the molecule, that is, which atoms are connected by significant bonds (covalent or coordination, I suppose). For that purpose, drawing 5 can be "read" at a glance, whereas 4 probably takes a fraction of a second more, and 1 and 3 quite a bit more. (As for 2, it conveys the same information as 4 but is somewhat uglier, typographically speaking.) All the best, --Jorge Stolfi (talk) 01:31, 22 May 2009 (UTC)

Can I add that the data on Wikipedia:Manual_of_Style_(chemistry)/Structure_drawing#Drawing_in_IsisDraw, specifically states to use the JACS drawing template and change the hydrogen settings to "On hetero". If you do that then you just get the "normal" standard structure, with no "C"s and no "H"s - except those on nitrogen, etc. I prefer to see terminal methyls as CH3, but applying the settings stated, prevents that.  Ronhjones  ^(Talk) 20:36, 21 May 2009 (UTC)

It is not up to us to invent or to promote obscure and non-standard molecule drawing styles. 1 and 3 are nightmares without being easier to read for beginners as they would have to know the meaning of those wedged bonds to understand the structure. I would strongly prefer the commonly used style 5 to show connectivity in combination with a skeletal formula and a 3D image to show spatial arrangement and conformation. In the long run I would like to see a molecule applet that allows 3D rotation. Cacycle (talk) 12:43, 22 May 2009 (UTC)

I don't know what I prefer - it's between 4 and 5. Linear alkanes aren't a problem, but acetone looks wrong drawn in the style of 5:

Ben (talk) 12:55, 22 May 2009 (UTC)

Most of the basic chem articles are pretty good, image-wise. Also the intended audience is generally not high school students. A related challenge is that biologists, not unlike high schoolers, are also challenged by complex organic chemistry - so that is an audience we'd like to hear from. The importance of bio-molecules is reinforced by the discussion at chemicals about Pubmed hits for chemicals. The bio-building blocks (sugars, amino acids, and cofactors) are often poor or irregular. Comparing these molecules is hard enough when the drawing format is uniform and one understands stereochemistry.--Smokefoot (talk) 13:15, 22 May 2009 (UTC)

It's true that in the US high schoolers don't see organic molecules, but that's not true everywhere - in the UK, the A-level syllabus covers much of what is sophomore organic chemistry in the US. And several other places do a similar thing, I think. But certainly when I did A-level we were not taught skeletal formulae - that wasn't taught until college level - but maybe things are different now. Walkerma (talk) 02:38, 23 May 2009 (UTC)

I was introduced to skeletal formulae at A-level (20 years ago), although only near the end of the course. The French baccalauréate is similar: the kids see and manipulate a few skeletal formulae, but it's hardly central to the OrgChem that's covered. Physchim62 (talk) 09:41, 23 May 2009 (UTC)

I don't see what is wrong with the acetone diagram above. Indeed, in the acetone article, methinks that the skeletal diagram at the top left is of little use, for laymen and experts alike. and should be replaced by the "roadkill diagram" above. To show the 3D geometry, one can hardly beat the ball and stick model at the lower left. Check out also 1,2-dioxetane (where the skeletal diagram is quite useless) and dodecahydroxycyclohexane (where the 3D model shows also the uncertainty ellipsoids from X-ray cryst.). All the best, --Jorge Stolfi (talk) 13:15, 23 May 2009 (UTC)

The skeletal diagram in 1,2-dioxetane is not at all useless. It is by far simplest way of conveying information about the structure of 1,2-dioxetane. ChemNerd (talk) 20:32, 23 May 2009 (UTC)

Seems terribly close-minded to dismiss what one does not understand well as useless. This is the language of chemistry, and to discuss chemistry in any but the most introductory topics, users should be fluent in it. --Rifleman 82 (talk) 22:06, 23 May 2009 (UTC)

I disagree that skeletal formulae are useless for acetone, 1,2-dioxetane and dodecahydroxycyclohexane. I agree that it is important that other representations of molecular structure are also given in these articles. I see and draw acetone skeletally all the time when I'm studying organic chemistry - other representations are rarely used.

The very reason that we want to show more than just skeletal formulae in articles is one of the best reasons for keeping them - skeletal formulae are difficult to understand for many people, and Wikipedia can help them. It's useful to be able to use Wikipedia to check that a skeletal formula is correct and compare it with other 2D or 3D representations, even if you initially need or prefer a more explicit structure to better understand the molecule.

Ben (talk) 18:14, 23 May 2009 (UTC)

My preference is to have at minimum a skeletal formula in every nearly every organic chemical article. These images provide simple connectivity information and are easily understood by anyone with basic training in organic chemistry. A second ball-and-stick or space-filling image, in "3D", is often very helpful for the depiction of conformational information. Ben's images are fantastic in this respect. Adding images that show each atom explicitly are beneficial, too, but only for the simplest molecules. I wouldn't include them for anything with more than about six carbons. The chembox can easily accommodate multiple images - there's no reason we shouldn't use this capability to illustrate chemical articles with images in more than one style. -- Ed (Edgar181) 13:20, 22 May 2009 (UTC)

I don't mind "most" but I think "every chemical article" is too much. Do you really think that ethane needs a skeletal formula? Methanol? I think there are some molecules that are so simple that a skeletal formula just looks odd. Walkerma (talk) 02:38, 23 May 2009 (UTC)

Methane, for example! Physchim62 (talk) 09:41, 23 May 2009 (UTC)

OK, not quite every. I don't need to illustrate methane with this: . -- Ed (Edgar181) 19:43, 23 May 2009 (UTC)

Jmol on wikipedia

Over recent weeks discussion on the Jmol list about getting Jmol installed on wikipedia has intensified, with some particularly good discussion recently. I think this is the time to make a final push to convince the WMF tech people to install the jmol mediawiki extension and allow it use. Further discussion should take place at Wikipedia:Using Jmol to display molecular models or its talk page. Recent discussion has suggested that use be enabled within the chemical infobox. A really good example of the use of the Jmol extension on a wiki is on Proeopedia here. Details of the jmol email list are here. You will also find examples of the use of the extension on the Jmol Wiki itself. We need to show that we want this.--Bduke (Discussion) 22:40, 26 May 2009 (UTC)

This would be great. In the absence of Jmol functionality on Wikipedia, I have been working with Jmol on my own website.

It doesn't take too long to get used to the coding - if you can do HTML, you'll be fine with Jmol.

Ben (talk) 23:32, 26 May 2009 (UTC)

Octahedral compounds

I created Category:Octahedral compounds a little bit ago, because I was looking for some kind of list of such compounds and didn't really find anything. I added a few compounds to this category, but then received a message on my talk page from Smokefoot informing me that octahedral compounds are extremely common and perhaps my effort was misguided, so I stopped.

Is it worthwhile to categorize compounds by molecular shape like this? If a system is ever developed to find intersections of categories, as I have heard rumors of from time to time, it seems that such a categorization might be useful.

I should point out that my chemistry knowledge is not very deep. —Bkell (talk) 01:30, 27 May 2009 (UTC)

DuPont and C-8

Could someone check the chemistry and health statements in DuPont and C-8, please. Even comments on the talk page would help. (I don't know if there is a better wikiproject to consult on this). Thank you. RJFJR (talk) 16:31, 27 May 2009 (UTC)

Let's see how long this solution lasts! It's the best solution, but it might need more work doing on it. Physchim62 (talk) 18:39, 27 May 2009 (UTC)

Quality!

Ben (talk) 20:01, 27 May 2009 (UTC)

IMHO that is a non-sense redirect: either keeping or nominating for deletion. --Leyo 07:44, 28 May 2009 (UTC)

Questchin

Hey guys, I'm currently a member of WikiProject Pharmacology. I've been assessing articles for a little bit and I have a question. Will you cover Pharmaceutical compounds or will you not even deal with medical drugs at all? A lot of the new articles are about compounds and stuff, and I'm wondering what would be within your project's scope. Thanks! Renaissancee (talk) 23:16, 2 June 2009 (UTC)

• There are so many medical drug articles! Taking Phenicarbazide as an example, chemists would like to know what compound class the drug belongs to (a semicarbazide). The chemistry information box is also different, there may be a problem there V8rik (talk) 21:19, 3 June 2009 (UTC)

Benzoic acid = stronger acid?

I m confused , if benzoic acid is a strong acid or not. If not then, which is the commonly known strong organic acid. —Preceding unsigned comment added by 115.127.15.19 (talk) 02:04, 4 June 2009 (UTC)

Our Strong acid article is a good place to start...has an explanation of what "strong" actually means in this context and list of some common strong acids. Then you can look at the acidity (pKa value) of any acid you like, for example benzoic acid, and see how it compares. While there may be some carboxylic acids (the common type of "organic acid") that are strong, they are much weaker than HCl and other "strong acids". Maybe some sulfonic acids or organosulfates could be similar in strength to sulfuric acid? Methanium is a super acid, and many other carbocations have very low pKa, but these would have to be used in solvents other than water because they are so reactive. DMacks (talk) 07:26, 4 June 2009 (UTC)

Oxygen isotopes for deletion

Oxygen-24 , Oxygen-15 , Oxygen-13 - have been nominated for deletion. 70.29.208.129 (talk) 07:14, 4 June 2009 (UTC)

Linezolid

Could someone have a look at the Synthesis section I've just added to Linezolid and improve/correct as necessary? I'll try to add some images later. Thanks in advance, Fvasconcellos (t·c) 17:42, 8 June 2009 (UTC)

That looks good for a short section. Given the complexity, it might be better to start thinking already about a Synthesis of linezolid article, and keeping this section as at summary. Physchim62 (talk) 13:37, 9 June 2009 (UTC)

Induction plasma technology

We have a submission at WP:AFC on the above subject. There are a few problems with it, but I'm wondering if it might have some potential. It can be found at Wikipedia:Articles for creation/Induction plasma technology and any comments at the discussion would be appreciated. Thanks. — Martin (MSGJ · talk) 11:01, 9 June 2009 (UTC)

Conductive polymers and related themes

The area of conductive polymers continues to be of contemporary interest, unfortunately this and some related article have become the domain of User:Pproctor who has strong views on the history and is embittered by the Nobel in the area (to Shirakawa et al.). PProctor's signature is the figure of the "melanin-based voltage controlled device" published by John McGinness, (possibly Pproctor's thesis advisor, candidate for AfD, and "who pioneered much of the modern field of organic electronics."). See: Organic electronics, melanin (which has been partially redefined), molecular electronics, organic semiconductor, and of course John McGinness. I have periodically but unsuccessfully tried to edit in this space. This curious situation that has persisted for years.--Smokefoot (talk) 12:58, 9 June 2009 (UTC)

Indeed, I can remember previous complaints about the state of these articles. We really need to get a cleanup plan together: Wikipedia is NOT a tool to rewrite history! Physchim62 (talk) 13:34, 9 June 2009 (UTC)

Favorite chemistry images

WikiProject Chemistry should be the featured WikiProject in next week's Wikipedia Signpost, assuming there are no last minute hitches! I'm looking for images to illustrate the piece, so I thought I'd ask here to see what are your favorities from our articles! The only criterion is that the image must be used in at least one WP:CHEMISTRY article, although I'll give priority to images produced by project members if there are enough suggestions to choose between. Physchim62 (talk) 13:43, 11 June 2009 (UTC)

I'll nominate File:Grubbs-1G-3D-balls.png (colorful pretty picture, used in Grubbs catalyst, of interest to multiple branches of chemistry...) You could choose just about any of Ben's images, though. -- Ed (Edgar181) 15:06, 11 June 2009 (UTC)

Diamond FAR

As Physchim62 wrote in his interview for that ^ Signpost article, it looked a poor FA, so I've nominated it for review. I have nominated Diamond for a featured article review here. Please join the discussion on whether this article meets featured article criteria. Articles are typically reviewed for two weeks. If substantial concerns are not addressed during the review period, the article will be moved to the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Remove" the article's featured status. The instructions for the review process are here. - Jarry1250 ^{(t, c)} 18:31, 13 June 2009 (UTC)

Reactionbox

After the last IRC discussion, I tried to have a go at creating an infobox for chemical reactions. I have set up a base in my userspace in User:Beetstra/ReactionBox/Reactionbox, based on the {{chembox}}. An example page having the box is in User:Beetstra/ReactionBox. I have not implemented a lot of parameters yet, just to keep the system pretty small. Of course more parameters can be added, and we can also think of introducing sub-boxes like the chembox has (it actually already has one). Using the modular approach like the chembox can be expanded easily where needed.

I'd like you all to have a look at it (feel free to edit whatever you'd like to), and see if we can figure out if and where it breaks, and what we have to adapt to make it work for as many as possible pages (or if we have to abandon the idea at all). --Dirk Beetstra ^{T C} 11:41, 18 June 2009 (UTC)

Would it be possible to somehow differentiate the "important" reactants and products from the "incidental" ones? For example, the Swern oxidation is used when one wants to make aldehydes or ketones from alcohols, not for making hydrogen chloride and carbon dioxide from oxalyl chloride! I realize that the distinction can be subjective in some cases, but for most organic reactions it is pretty clear. --Itub (talk) 12:31, 18 June 2009 (UTC)

Different colouring? --Dirk Beetstra ^{T C} 12:58, 18 June 2009 (UTC)

Changed the colouring, bit more complex. There are some things possible here. --Dirk Beetstra ^{T C} 13:18, 18 June 2009 (UTC)

It's an interesting idea. A lot depends on where we'd deploy the "reaction box." It should be restricted to articles on reactions, vs articles on chemicals in general. Otherwise, we'd be inviting debates over which reactions are significant. The main use would be for organic reactions, since inorganic and organometallic chemistry is so untidy.--Smokefoot (talk) 13:13, 18 June 2009 (UTC)

It is mainly an experiment at the moment, Smokefoot. We may get stuck. For reactions, I am a bit working with this in mind. --Dirk Beetstra ^{T C} 13:18, 18 June 2009 (UTC)

I agree with Itub, we should try (at least for organic reactions) to distinguish between educts and reagents, and also probably catalysts as well. Anything that contributes carbons to the skeleton should be an educt; beyond that it gets a bit grey. For reduction of an aldehyde to an alcohol we'd probably tend to think of hydrogen gas (with a catalytic hydrogenation) as an educt, because the entire molecule is incorporated, but sodium borohydride as a reagent because only part of it is. Are there more precise definitions of these things? Does it even matter? Walkerma (talk) 13:53, 18 June 2009 (UTC)

Would it be immensely silly just to put the educts in bold and the reagents in normal type? That way we can argue about what is an educt and what is a reagent to our hearts' content, while still adding content to the articles ;) Physchim62 (talk) 14:13, 18 June 2009 (UTC)

We might also have problems with the term "educt"! IUPAC definitely prefers "reactant". Physchim62 (talk) 14:21, 18 June 2009 (UTC)

Bolding is simple, indeed. Will incorporate that. And I chose 'Reactant' for the name of the parameter. --Dirk Beetstra ^{T C} 14:34, 18 June 2009 (UTC)

I'm glad Beetstra has taken up this project. I did a mock-up last year at User:Rifleman_82/Infobox_reaction, perhaps it might give some ideas? I'm not keen on listing the reagents/starting materials to such detail. Perhaps a list, instead? After all, we typically have a general reaction scheme as well. I think that a mention of the history is nice as well, especially for named reactions. --Rifleman 82 (talk) 14:43, 18 June 2009 (UTC)

I chose this in stead of a one-parameter-list because this data can easily be turned into a database, might be searchable in the end, and is maybe easier to control. --Dirk Beetstra ^{T C} 14:46, 18 June 2009 (UTC)

On a closely related topic, I have added a suggestion for naming conventions for name reactions at WT:NCCHEM: please take a look at it and lets see what needs modifying. Physchim62 (talk) 15:19, 20 June 2009 (UTC)

The box has been copied to template space, {{Reactionbox}} is live. --Dirk Beetstra ^{T C} 13:21, 22 June 2009 (UTC)

I also made User:CheMoBot follow edits to the template-transclusions, see Wikipedia:WikiProject Chemistry/ReactionIndex and Wikipedia:WikiProject Chemistry/ReactionLog. --Dirk Beetstra ^{T C} 16:59, 22 June 2009 (UTC)

Mixed oxide

Do we need the page Mixed oxide, it reads strange and from my point of view it misses the most wanted examples.--Stone (talk) 17:03, 23 June 2009 (UTC)

Additionally it links to vanadates and other oxoanions which for me are no mixed oxides.--Stone (talk) 17:04, 23 June 2009 (UTC)

Probably that article should be redirected to oxide. Other strange articles in that realm: Toxic metals and Gold saltss. --Smokefoot (talk) 17:28, 23 June 2009 (UTC)

Yeah, the Mixed oxide page is rubbish, but to my mind the Toxic metals and Gold salts pages are actually useful. We sometimes forget that non-chemists use chemistry too, and may even use chemical terminology in a way that we would disagree with but which is widely accepted in their sphere, and I think the latter two fall into that category. Chris (talk) 20:54, 1 July 2009 (UTC)

Page name

beta-Carotene is currently named, well, beta-Carotene. I'm not sure about the hyphening and capitalization and am unfamiliar with either chemistry or the naming guidelines for chemicals. Could an informed participant comment on talk:beta-Carotene?

Page is also a bit of a stub. WLU (t) (c) Wikipedia's rules:^simple/_complex 13:57, 24 June 2009 (UTC)

What is the difference between

Neutralization (chemistry) and Acid-alkali reaction. Should we merge it?--Stone (talk) 17:14, 25 June 2009 (UTC)

Useless redirects

Pikiwyn (talk · contribs) makes many redirects of chemical formulas. Impo this is nonsense: (1) one hardly matches all chemicals with a specific formula, (2) this is a never ending story (wikipedia doesn't list all chmicals), (3) who is looking for e.g. “C₆O₈H₆” instead of ascorbic acid??? Opinions? --Yikrazuul (talk) 10:06, 1 July 2009 (UTC)

A typing error caused me to look for C6H8O6, which was hit 320 times during June: it is, course, the correct empircal formula for Ascorbic acid, not the one quoted above. C6H12O6 (glucose) was hit 4733 times. Physchim62 (talk) 13:48, 2 July 2009 (UTC)

CH4 and CH3COOH were made back in 2004; disambig C2H4O2 in 2005. A quick scan shows me most are following the normal convention of the formulae (C, H first, then the rest alphabetical). Discussable, maybe, but certainly not nonsense nor useless. --Dirk Beetstra ^{T C} 10:19, 1 July 2009 (UTC)(adapted Dirk Beetstra ^{T C} 10:41, 1 July 2009 (UTC))

I find formula redirects useful, and redirects are cheap (certainly not harmful). --Itub (talk) 12:46, 1 July 2009 (UTC)

These redirects are at worst a waste of time and more likely useful to some one. It's the "See also's" I often find semi-useless and even distracting, and potentially endless.--Smokefoot (talk) 13:02, 1 July 2009 (UTC)

I think both redirects and disambiguation pages for molecular formulas are useful. For example, Wikipedia should be able to answer the perfectly plausible question, "What are the common isomers of C₄H₁₀O?" This is answered by the disambig page at C4H10O. Looking at page stats for C8H10N4O2 shows that it got 113 hits last month. If thousands of people a year search Wikipedia for C8H10N4O2, we had better have a redirect at C8H10N4O2 to send them to caffeine. -- Ed (Edgar181) 16:42, 1 July 2009 (UTC)

I think the molecular formulas as separate entries are useful (Hill order please). For molecular formulas, except for the simplest ones, I think disambig pages would be preferred. Even if we only have one compound with that formula now, we could easily have additional ones if the future. The disambig page Butyl chloride is a good example, showing two butyl chlorides and two others we might add in the future. So I'm switching the C4H9Cl redirect to a disambig (or maybe a redirect to the butyl chloride disambig). Are we better off having two disambigs in such cases or one disambig and one redirect? ChemGardener (talk) 02:15, 2 July 2009 (UTC)

I think the redirects are useful and can only improve Wikipedia. There have been a lot of times when I see only a formula and would like to know more about the chemical, and I'm sure I'm not the only person. - (Pikiwyn (talk) 12:12, 2 July 2009 (UTC))

These redirects don't hurt anyone (except the person that has to add them) and are useful: certainly far more useful that List of organic compounds, for example. CH4 got more than 2000 hits last month, SO2 got more than 4000, even FeCl3 was hit 858 times. I could go on: NaCl, 6112 hits; CH3COCH3, 116 hits; C2H5OH, 431 hits; C6H6, 1511 hits. These are far higher hit counts than many featured articles! Physchim62 (talk) 13:39, 2 July 2009 (UTC)

I think instead of dab pages, they should be WP:SETINDEXes, using the {{SIA}} template instead of the {{disambig}} template. 70.29.208.69 (talk) 06:25, 5 July 2009 (UTC)

Ok, I agree that lemmata of smaller and more popular molecules like CH4 or C6H6O6 are beneficial. I thought that the search of something like C43H58N4O12 instead of Rifampicin is senseless. Cheers, --Yikrazuul (talk) 11:44, 5 July 2009 (UTC)

Suggestion for formulas in lede

In general, I suggest that formulas in the lede should be structural in nature, not empirical formulas. Two reasons: the ChemBox already has the empirical formula (and we aim not to repeat ourselves) and (2) structural formulas convey additional information. Thus, for butanol, we'd have C₄H₁₀O in ChemBox, but in the lede we'd have CH₃CH₂CH₂CH₂OH, CH₃(CH₂)₃OH, or C₄H₉OH (I prefer the middle one). For large molecules like lysergic acid, there is not much that can be done, so we'd not even mention formulas in the lede.--Smokefoot (talk) 13:02, 1 July 2009 (UTC)

I agree. --Dirk Beetstra ^{T C} 13:16, 1 July 2009 (UTC)

Me too. Physchim62 (talk) 13:53, 1 July 2009 (UTC)

Structural formulas in the lede are certainly good. But, for simple chemicals, I see no harm to give also the empirical formula. The infobox is not really part of the article; it is not in the normal text reading order and may be hard to read e.g. for people browsing from a small-screen device or a text-to-speech interface. Besides, in some cases (such as C₁₂H₁₂, C₃F₈, C₆₀, etc.) the empirical formula may convey useful information that is harder to see in a structural formula.
Methinks that the decision should be made for each article. As in most other issues, one should not disimprove the text of an article just to make it conform to some aritrary standard. All the best, --Jorge Stolfi (talk) 04:01, 2 July 2009 (UTC)

Agree. I do not see a reason to have empirical formulas for organic molecules in the intro section. Structural ones might be useful for some articles and this can be decided on an article base. Cacycle (talk) 13:02, 2 July 2009 (UTC)

Avogadro: constant vs. number

There is a slow but pernicious editing dispute going on over the first sentence of the Avogadro constant article, which has wider implications as well. I am involved, so I shall refrain from comment here except to point to the talk page discussion. Outside opinions are welcome. Physchim62 (talk) 23:20, 2 July 2009 (UTC)

Georges Darzens

Does anyone have access to this bulletin and this articel. If yes, it would be fine to get a copy. Many thanks for your help and greetings --benutzer:Roland1952 (talk) 15:36, 3 July 2009 (UTC)

r410a

who knows normal operating pressures for r410a a/c system —Preceding unsigned comment added by 99.145.128.169 (talk) 18:26, 3 July 2009 (UTC)

Our R410a article is pretty sparse on those details, but googling around, I've seen comments that it's 1.5-2x higher than R22. DMacks (talk) 18:42, 3 July 2009 (UTC)

New palladium articles

• Bis(triphenylphosphine)palladium(II)_dichloride
• Palladium-catalyzed coupling reactions

--Rifleman 82 (talk) 15:10, 5 July 2009 (UTC)

GA Sweeps Reassessment of Steel

Steel has been nominated for a good article reassessment. Please leave your comments and help us to return the article to good article quality. If concerns are not addressed during the review period, the good article status will be removed from the article. Reviewers' concerns are here. Ruslik_Zero 12:35, 6 July 2009 (UTC)

A new way of setting out metabolic pathway schemes

Biochemie und Pathobiochemie (biochemistry and pathobiochemistry), zh:胆固醇生物合成 (biosynthesis of cholesterol). Just thought it might be a better way to illustrate biochemical pathways than just images. --Choij (talk) 12:08, 7 July 2009 (UTC)

I especially like the Chinese version: maybe we can try to see if something similar is possible in English. Physchim62 (talk) 12:52, 7 July 2009 (UTC)

Formula redirects

So, C22H25NO6 is recently created as a redirct to colchicine. There must be many species with the formula C₂₂H₂₅NO₆. It is conceivable that non-technical readers would conclude that C22H25NO6 uniquely identifies one compound. The creation of articles that summarize the structural isomers of simple formulas might be useful, but for the larger formulas ...? --Smokefoot (talk) 18:00, 7 July 2009 (UTC)

If more follow, it can turn into a disambig, or an index page. Not very useful, probably, but also not harmful. --Dirk Beetstra ^{T C} 18:06, 7 July 2009 (UTC)

Redirect to chemical formula ;-) Cacycle (talk) 18:45, 7 July 2009 (UTC)

Here are some more C₂₂H₂₅NO₆ compounds:

• cyanoethyl sym-dibenzo-16-crown-5 ether
• 1,4-(acetyletheno)-2,2-dimethoxy-4a-(ethoxycarbonylmethyl)-1,2,3,4,4a,9a-hexahydrocarbazole
• isocolchicine
• mecambridine
• allocolchicine
• methyl 4,6-dimethyl-2-(4-nitrobenzoyloxy)decahydro-2,6-methanocyclobuta(a)pentalene-4-carboxylate

Ben (talk) 19:08, 7 July 2009 (UTC)

We also have the Dictionary of chemical formulas/* pages, yet another apparently non-maintained approach to formula indexing:( On the other hand, searching via WP search or google with site:en.wikipedia.org for the formula doesn't even find the redirect or the colchicine page. Why the heck not? DMacks (talk) 19:21, 7 July 2009 (UTC)

It takes a bit of time before Google picks it up. --Dirk Beetstra ^{T C} 21:05, 7 July 2009 (UTC)

Ah yeah, searching via wikipedia or google for C6H12O6 finds what I'd expect. Given that's an existing and automatic (even if slightly lagged) way to search, is it worth creating another one that must be updated manually? DMacks (talk) 21:12, 7 July 2009 (UTC)

Correction: wikipedia's internal search does not find glucose for C6H12H6. DMacks (talk) 21:14, 7 July 2009 (UTC)

C6H12H6 or C6H12O6? Does that explain it?

Ben (talk) 21:41, 7 July 2009 (UTC)

Not at all...my typo in explaining the problem doesn't solve the problem. A fulltext search for the formula does not find glucose whereas a google search does. Point being there are existing maintenance-free ways of being able to find all compounds with a given formula. I thought one of the goals of the whole validation, chembox cleanup, etc project is to make our articles searchable/machine-indexable? DMacks (talk) 03:19, 8 July 2009 (UTC)

The wikipedia search on 'C6H12O6' finds the formula redirects/disambigs. Which does lead to the correct compounds, so that part is good. It is even the main result.

It does however not find any of the sugars in the main results. The second result is Acid-citrate-dextrose, which has in the text |[[Dextrose]] (C6H12O6*H2O) ||23.28g to 25.73g, an unformatted formula. The third result is Ribulose-1,5-bisphosphate, which has 2 G3P = 1 C6H12O6 (glucose) All a matter of 'bad formatting'...

Glucose (e.g.) does not have that, there it is (in the chembox): | Formula = C₆H₁₂O₆ In other Chemboxes it might be | C = 6 | H = 12 | O = 6, so they will not show up here.

The google engine removes the tagging, so that one does find Glucose, and the others off course. The Wiki engine is apparently a bit more picky. In either way, this is why these redirects are quite handy. They are the top result, both in Google and in the Wiki search. I therefore think, at least for now, that these redirects/disambigs might even be handy, even for the strange ones. --Dirk Beetstra ^{T C} 08:09, 8 July 2009 (UTC)

In the meantime, for important articles, could we add hidden unformatted formulae, e.g. <!-- C6H12O6 --> for glucose et al?

Ben (talk) 11:09, 8 July 2009 (UTC)

I would suggest adding a 'plainformula =' to the chemboxes. The field does not exist, and will be ignored, still we could use it in some way later if needed. --Dirk Beetstra ^{T C} 18:19, 8 July 2009 (UTC)

Sounds good.

Ben (talk) 21:33, 8 July 2009 (UTC)

If it is not used (i.e. not in the page sent to the browser) then a search engine cannot index it. We sould instead hide it somehow from being displayed while having it in the page code. Cacycle (talk) 01:06, 9 July 2009 (UTC)

True, did not think about that (I believe it is only true for the Google search, though, not for the internal search), we'll have to figure something out in the future. I was myself thinking about a (hidden?) category system (Category:Compounds with formula C6H12O6, a subcategory of Category:Compounds by formula?). --Dirk Beetstra ^{T C} 09:57, 9 July 2009 (UTC)

My 2 cents: seems like a lot of unnecessary work to explicitly add the unformatted formulae in whatever form. I find it totally unjustifiable for any but the simplest compounds most frequently accessed by the non-scientist public. Is there a way we can harvest the data in the formula code (e.g. C=6 | H = 12 | O = 6 ) such that we can search for compounds using a dedicated search page? Something like the way SDBS does it? (http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng) --Rifleman 82 (talk) 10:14, 9 July 2009 (UTC)

Of course we can 'craft' the same formula from those fields (and that is a very useful, quick and proper way of doing it, the only 'problem' is, how to get it 'hidden' in the pagecontents. Searching that will not be possible on-wiki (I tried that once with an extension, but they are not too keen on that. Maybe on-toolserver!). --Dirk Beetstra ^{T C} 10:35, 9 July 2009 (UTC)

Use white-colored text? --Rifleman 82 (talk) 03:19, 14 July 2009 (UTC)

To find formulas using mediawiki search you need to add spaces: search for "C 6 H 12 O 6" (with the quotes). --Itub (talk) 12:32, 9 July 2009 (UTC)

Hmm, but how to transfer that knowledge to the n00b around the corner? I would have typed C6H12O6, and would have been happy with finding the article C6H12O6 which brings me further. That would go for all such redirect in the end, might be a quite powerful find then. Still, having Glucose and the other sugars in the results for that search would require the plain-text "C6H12O6" to appear in the code. --Dirk Beetstra ^{T C} 14:59, 13 July 2009 (UTC)

Soap

The last section of the article on soap states that metals added to soap have a certain function Nanoscopic metals are commonly added to certain soaps specifically for both coloration and anti-bacterial properties. Titanium powder is commonly used in extreme "white" soaps for these purposes; nickel, aluminum and silver are less commonly used. These metals provide electron-robbing behavior when in contact with bacteria, stripping electrons from the organism's surface and thereby disrupting their functioning (typically killing the bacteria when it has lost too many electrons). For me this sounds a little bit strange, but somebody has a clue if this is right. The pure white is most of the time titanium oxide and to ad nanopwdered nickle to soap sounds like a big funny surprise for most of the people who are alergic to nickel. Thanks.--Stone (talk) 13:27, 9 July 2009 (UTC)

This is entirely original research, but I'm allergic to nickel and have never had an allergic reaction to soap. shoy (reactions) 18:36, 9 July 2009 (UTC)

How do Quats relate to Anaerobic Waste Water Lagoons

Is there a test out that will tell you how many ppm of Quat you have in your lagoon system? —Preceding unsigned comment added by 76.84.128.43 (talk) 20:25, 9 July 2009 (UTC)

Pageview stats

After a recent request, I added WikiProject Chemistry to the list of projects to compile monthly pageview stats for. The data is the same used by http://stats.grok.se/en/ but the program is different, and includes the aggregate views from all redirects to each page. The stats are at Wikipedia:WikiProject Chemistry/Popular pages.

The page will be updated monthly with new data. The edits aren't marked as bot edits, so they will show up in watchlists. If you have any comments or suggestions, please let me know. Thanks! Mr.Z-man 20:31, 9 July 2009 (UTC)

Thank you! --Rifleman 82 (talk) 01:48, 10 July 2009 (UTC)

Fiberglass GA Sweeps: On Hold

I have reviewed Fiberglass for GA Sweeps to determine if it still qualifies as a Good Article. In reviewing the article I have found several issues, which I have detailed here. Since the article falls under the scope of this project, I figured you would be interested in contributing to further improve the article. Please comment there to help the article maintain its GA status. If you have any questions, let me know on my talk page and I'll get back to you as soon as I can. --Happy editing! Nehrams2020 (talk • contrib) 23:34, 11 July 2009 (UTC)

Changes to popular pages lists

There are a few important changes to the popular pages system. A quick summary:

• The "importance" ranking (for projects that use it) will be included in the lists along with assessment.
• The default list size has been lowered to 500 entries (from 1000)
• I've set up a project on the Toolserver for the popular pages - tools:~alexz/pop/.
  • This includes a page to view the results for projects, including the in-progress results from the current month. Currently this can only show the results from a single project in one month. Features to see multiple projects or multiple months may be added later.
  • This includes a new interface for making requests to add a new project to the list.
  • There is also a form to request a change to the configuration for a project. Currently the configurable options are the size of the on-wiki list and the project subpage used for the list.
• The on-wiki list should be generated and posted in a more timely and consistent manner than before.
• The data is now retained indefinitely.
• The script used to generate the pages has changed. The output should be the same. Please report any apparent inconsistencies (see below).
• Bugs and feature requests should be reported using the Toolserver's bug tracker for "alexz's tools" - [4]

-- Mr.Z-man 23:53, 11 July 2009 (UTC)

Skeletal formulae with terminal methyl groups?

On the commons, I have a gallery with skeletal formulae created. It contains formulae with terminal methyl groups. Now User:Leyo in the German WikiProject Chemistry pointed out that in English skeletal formulae may not contain methyl groups. Do I need to replace every formulae or will also be accepted? --Hystrix (talk) 18:05, 15 July 2009 (UTC)

We just discussed this recently, because we didn't have a clear policy on it. You can see the policy summarized here. We avoid using "Me" (common in English publications) in order to keep our German colleagues happy :). Your structures for things like methanol, acetylcholine, etc are fine for en, but things like hexane or hexan-1-ol would normally be drawn without explicit methyl groups (unless you're K. C. Nicolaou!). Thanks for checking in with us! Walkerma (talk) 22:19, 15 July 2009 (UTC)

Oops! I was wrong - it appears that the consensus was to allow the "Nicolaou style" so it looks like your structure DO fit our style guide! Walkerma (talk) 22:22, 15 July 2009 (UTC)

Yes, we decided to allow Nicolaou style as an option, as it becoming more widely used – it is still probably a minority style, but it is significant, so we don't ban it! In general, we welcome having lots of different representations of the same molecule available on Commons, as this gives more choice to users and illustrates that there is not a single "correct" way to do things. Physchim62 (talk) 10:57, 16 July 2009 (UTC)

Pronouncing methyl groups is good unless the molecule is suitable. Bigger structures (e. g. that) are easier to draw without all those terminal Me-groups. Cheers, --Yikrazuul (talk) 12:45, 17 July 2009 (UTC)

PubMed tool for generating SVG structures

I found a tool for generating SVG diagrams based on the SMILES code, and this is the first structure I made with it: File:Hydroxypethidine.svg. Is this acceptable? —harej (talk) (cool!) 08:34, 17 July 2009 (UTC)

You are missing the hydrogen on the heteroatom (O-oxygen). While PubMed likes to do it, it is not popular or preferred in general. --Rifleman 82 (talk) 09:22, 17 July 2009 (UTC)

I've also noticed that the tool is not good at indicating positions in 3D space. I'll try to find a different tool. Feel free to revert the change I made to Hydroxypethidine. —harej (talk) (cool!) 09:26, 17 July 2009 (UTC)

I fixed the problem. It's possible that the faults lie in the SMILES, since I get the same issue in BKchem. —harej (talk) (cool!) 09:44, 17 July 2009 (UTC)

I think the structure looks reasonably well, but the resolution is a too low for some uses. Human-drawn structures are likely to be better but take more time, so it's just a matter of cost vs benefit. --Itub (talk) 12:01, 17 July 2009 (UTC)

I agree, since one can choose how to orientate a formula. Cheers, --Yikrazuul (talk) 12:35, 17 July 2009 (UTC)

Movies

File:Test movie.gif

nice, but useless? (16 color version, 380 kB)

turning around (16 color version, 500kB)

Playing around with PyMOL I made some first movies. Is there any advantage to have some? The problem is: they are relativly big in size (depending how many frames are used, colors in the gif-files, size).--Yikrazuul (talk) 16:25, 17 July 2009 (UTC)

Second version is much better, but maybe make it slower? —harej (talk) (cool!) 18:02, 17 July 2009 (UTC)

Much too fast. I have seen such fast speeds for some small molecules on Wikipedia and these are pretty useless, 15 - 20 s per turn would be better. Is there any reason for the obtrusive black background? I think it should be white (as the page backgrounds on Wikipedia). Also, animated graphics are extremely distracting in articles, the better alternative might be still stereo pairs if you really have to provide accurate 3D information. In general, I think that a single still image is better as the additional stereo information from animated proteins does not contribute much (if anything) to Wikipedia articles. Cacycle (talk) 03:47, 21 July 2009 (UTC)

Thx for the responses. I have to admit that recently I've begun to learn about movie-making in PyMOL. The only advantage (impo) of movies would be the gain of one an additional dimension (3D) hence one see e. g. how the substrate is held by the enzyme. I will change the background of "normal" 2D-pics to white or transparent, respectively. --Yikrazuul (talk) 11:13, 24 July 2009 (UTC)

Article: cell casting may be inaccurate

I'm not very familiar with Chemistry... I came upon the cell casting article while wikifying it -- and I suspect it may be inaccurate. In the original article it says cell casting is an inferior method of producing PMMA sheets, when the main article (PMMA) says otherwise! I also wonder if there may be a need to merge both articles... --Kryssolis (talk) 03:00, 19 July 2009 (UTC)

Bolding

I've noticed with some articles like Malachite green at the beginning the name of the chemical and its other names are bolded, but with other articles like Maleic anhydride they aren't or aren't completely and i was wondering which is right. Is the bolded wrong or is the unbolded just still needing to be bolded? Pikiwyn (talk) 20:45, 19 July 2009 (UTC)

According to the Manual of Style (WP:BOLDTITLE): "If the subject of the page has a common abbreviation or more than one name, the abbreviation (in parentheses) and each additional name should be in boldface on its first appearance." Chemistry articles should follow this convention. -- Ed (Edgar181) 21:39, 19 July 2009 (UTC)

Thanks for your help Pikiwyn (talk) 21:58, 19 July 2009 (UTC)

I suggest however that articles on chemical compounds differ from most other articles in Wikipedia because so many names apply to any given compound, sometimes dozens of names. Few other areas within Wikipedia share this property. We should recognize that the topic of chemical compounds (not other chemical phenomena, just chemical names) is different and that we should therefore choose to deviate from the usual MOS (If necessary, we could plead before the wikicourt of MOS folk for a variance). Furthermore, we might consider moving all but the most prominent names to the "other names" slot on the ChemBox. --Smokefoot (talk) 22:04, 19 July 2009 (UTC)

I agree entirely with Smokefoot. Malachite green has far too many bolded names. The bolding is not necessary. It would indeed also be better to move many alternative names to the infobox. --Bduke (Discussion) 22:46, 19 July 2009 (UTC)

I agree as well: when the problem is too many bolded names, the infobox is the answer! We need to be pragmatic about this, but too much boldface defeats the entire purpose of it being there. Physchim62 (talk) 23:22, 19 July 2009 (UTC)

Just want to add that I'm in agreement here. All listed synonyms should be in bold per MoS, but only common synonyms should appear in the first line of text. The chembox is well suited to list the others. -- Ed (Edgar181)

Charges and square brackets

Before I go changing them all, can we have a consensus on the position of charges. I'm thinking in particular of tetrafluoroammonium, where (to my mind) all the charges are in the wrong position. Furthermore, in salts like [NF⁺
₄]
₂TiF²⁻
₆, you don't need charges at all (unless especially trying to emphasise them for some reason), but the anion should have square brackets; I would write it as [NF₄]₂[TiF₆]. Thoughts? Chris (talk) 22:05, 20 July 2009 (UTC)

Is one style predominant in the literature? Does IUPAC have any rules on the matter?

Less esoteric compounds like ammonium chloride are often written without brackets, i.e. NH₄Cl. I would have thought this is OK unless it causes confusion – although I do like consistency.

Ben (talk) 22:17, 20 July 2009 (UTC)

Is it common for the superscripted text to be directly above the subscripted text? Or "after", horizontally? --Rifleman 82 (talk) 01:35, 21 July 2009 (UTC)

Having looked at the Red Book, if there is a charge it goes outside the brackets. There are no examples that I could see of charges and subscripts both being outside the brackets, because it's redundant; you only need the subscript if the ion is part of a compound, and in that case it's not usual to show the charge. So, it should be [NF₄]⁺, for example. I'll feel free to make changes :) Chris (talk) 08:03, 21 July 2009 (UTC)

PS: I've found an example that had both subscript and charge (top of p58). The subscript comes first, and the charge after it (not directly above it).

Sounds like a good policy.

I do see things like peroxide written O²⁻
₂. Are we saying we want that to become O₂²⁻ or [O₂]²⁻?

Ben (talk) 10:19, 21 July 2009 (UTC)

O₂²⁻ (p 73 of red book). You don't need square brackets because it's not a complex ion.Chris (talk) 10:38, 21 July 2009 (UTC)

My two bits: In the spirit of simplicity (fewer key strokes without sacrificing clarity), I prefer (NF₄)₂TiF₆ to [NF₄]₂[TiF₆]. But many authors like bracketing, especially for coordination compounds but it's unecessary for neutral compounds, at least in my view. On the other issue: the charge follows the number - sounds good.--Smokefoot (talk) 15:27, 21 July 2009 (UTC)

International Year of Chemistry

This is a new article - it looks to be well-written and researched, though perhaps it needs to be done in a more encylopedic style (though that is hard for a "future event"). I've added cats and a few links, but if those familiar with the topic could edit it a bit, I'd appreciate it. I think this would be a great candidate for WP:DYK, but I think WP:Chemistry people should pick it over before I nominate it. Cheers, Walkerma (talk) 17:44, 23 July 2009 (UTC)

Possibly, but the article in this form has been deleted for copyvio. Maybe a fresh rewrite is needed? --Dirk Beetstra ^{T C} 11:18, 24 July 2009 (UTC)

Bot probs with protein structures

I have opened a discussion about a certain bot on commons, look here. Please feel free to join the discussion! Cheers, --Yikrazuul (talk) 13:49, 28 July 2009 (UTC)

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