Wikipedia talk:WikiProject Chemistry/Archive 13

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IUPAC Gold Book

The maintainer of the IUPAC Goldbook, aka the IUPAC Compendium of Chemical Terminology, contacted OTRS (# 2007031310012846) offering a collaboration between IUPAC and Wikipedia and offering to make their data available to us (NOTE: I don't know if just for linking purposes, or for inclusion in Wikipedia itself). The Gold Book is a good source of short definitions for chemistry. Individual definitions in the Goldbook can be linked to from the web now, but they were offering to provide the definitions in a text format if we wanted them. Is this a commonly used or useful source? Does anyone have any ideas about how to incorporate this data? -- phoebe/(talk) 01:11, 6 April 2007 (UTC)

• Mememememememememememememememememememe! Wonderful news! We already link to Gold Book definitions where we can (have remembered to, have got round to, etc.), as these have a sort of "official" force, but the copyright problem has prevented us from being able to keep tracks on things in an organised way. For example, a list of Gold Book topics, even if it were just for the use of this WikiProject, would have fallen foul of WP copyright policy. I have a few ideas as to how we could fill the gaps in our coverage, but I'll give others the chance to put their word in first. Physchim62 (talk) 02:11, 6 April 2007 (UTC)
  • IUPAC is the authoritative source for many things in chemistry. We freely use much of their data and rely on their definitions but are careful to cite where appropriate. Most definitions must be rewordings of the meaning and spirit of the IUPAC definitions otherwise its plain wrong. If I understand their offer they are offering to waive copy write so that we do not worry about copy write issues and can even use the word for word definitions etc. IN addition it sounds like they would donate text that could go into wikisource from which we could copy paste freely (with proper citation of course). We of course need to continue to cite properly for other reasons. IUPAC's purpose is very consistent with this offer and it makes sense for them too. I would like to learn more.--Nick Y. 02:15, 6 April 2007 (UTC)
    • I'd completely forgotten about Wikisource but yes, I'm sure they'd love to have the Gold Book if they can. We should remember that there are lots of equations to mark up: I don't know if our contacts have them handy in TeX markup. If not, it will slow things down a bit but it's not a unsurmountable problem. Physchim62 (talk) 02:59, 6 April 2007 (UTC)

• All: I have no idea if they were offering to waive copyright or not. For now, LET'S ASSUME NOT -- please don't start copying IUPAC content :) They may have only been offering to try and help ease the linking process. I'll write the person back and ask, and mention Wikisource as well. -- phoebe/(talk) 03:21, 6 April 2007 (UTC)

People should probably be aware of Project Prospect, where IUPAC Gold Book is used as a glossary within online chemistry papers published by RSC, once you turn on "Advanced Features". Don't know what capillary electrophoresis is? It's highlighted in Gold - hold the mouse over it and you get the IUPAC Gold Book definition. It seems to me that if they're willing to do a deal like that with RSC, they should be willing to do the same with us. It also seems to me that we would like to see a feature as seamless as Project Prospect. Let's see what Phoebe can find on copyright. Thanks Phoebe! Walkerma 06:28, 6 April 2007 (UTC)

Such a feature is technically feasible on WP if the copyright situation allows. For example, an editor could type {{goldbook|absorbance}} to give absorbance. To be fully effective it would need the definition of a new class in the monobook.css file, but this is doable. To be implemented, it would also need the help of a kindly bot-operator, but I'm sure we could find one of those! Otherwise, what we could do with for a start is permission to place a wikilinked contents list on a project page: that way we can check which articles need links adding, and which articles need to be written from scratch. Physchim62 (talk) 10:45, 6 April 2007 (UTC)

BTW, technically feasible does not necessarily mean desirable: many would say that it is better for an editor to type [[absorbance]] to get absorbance (article which does not yet have a Gold Book link)! Physchim62 (talk) 11:00, 6 April 2007 (UTC)

This is exactly what I had in mind when I submitted this proposal to Wikipedia. I have already explained the situation to Phoebe Ayers in two emails, but as I did not receive any reply yet, I decided to use this forum directly. At present time we would like to offer an easier way to link to the Gold Book and probably some automatic way to link to Gold Book if the same term appears in both Wikipedia and Gold Book. Incorporation of complete Gold Book entries into the Wikipedia is something that would require much broader discussion inside IUPAC (see [1] for general information about copyright of IUPAC publications) and it would be great to have something smaller to begin with. I am the maintainer of the Gold Book website and data (not the content) and I am representing a small group of people around the XML version of Gold Book. Therefore the thing that we can offer right now is an easier way of linking to the Gold Book. I would be happy to discuss the technical aspects with anyone interested. Note: There will be the IUPAC General assembly in August and I think that this is a great opportunity to discuss the cooperation of IUPAC with Wikipedia inside IUPAC. If we have something available to show to the participants, it could really help them understand the value of this project. (Beda42 05:58, 16 May 2007 (UTC))

• My thoughts:
  • The Gold Book is great! Its WP page is linked to from over 50 pages. They are much better in identifying concepts than wikipedia and keeping strictly to one topic per page (not like WP merger-mania)
  • the Project Prospect is great! but should not be included in wikipedia. In that sense they are the competition (do not get me wrong, I love competition but), the goldbook links should not replace our internal linking system. If I follow the absorbance link I want to see the WP absorbance article not that of the gold book
  • Instead a bot should provide a reference on every WP page to the relevant gold book page with citation end of first sentence. All referencing to the gold book is now done manually and inconsistently and can better be handled by a bot. V8rik 13:10, 6 April 2007 (UTC)

• I agree. I feel we should have our own version of the definitions, but we should be able to reference Gold Book more tidily and easily. Automatically - maybe not. A bit difficult for that. --Rifleman 82 15:30, 6 April 2007 (UTC)

I agree with the general consensus above and do not see any real disagreement. Although word for word use of IUPAC definitions is useful sometimes and easier linking to IUPAC would be good, our content should remain unique, particularly in being more encyclopedic and informative than IUPAC. Internal linking is always first priority. The main advantage I see would be to write things such as ...the IUPAC definition of the term is "blah blah blah", however in practice many chemist use the term more widely to also include blah blah blah over the objection of the physical chemists. (A little sloppy and un-artful language but you get the point.)--Nick Y. 17:17, 6 April 2007 (UTC)

If there's anything I can do to help with improving links between Gold Book and Wikipedia, let me know, I'm very interested in these kinds of initiatives. If you would like a recent list of ~23000 chemistry articles from Wikipedia, Beda42, I can send one to you - perhaps you could see if it is worth linking to Wikipedia - though I appreciate that WP is not authoritative in the way Gold Book is. Physchim62 (and probably many others) is far more knowledgable than me on Gold Book, he would be a good person to talk with. Good to hear from you, Beda42. Walkerma 06:53, 16 May 2007 (UTC)

As I see it, the problem is almost entirely on WP's side: we know where the Gold Book definitions are, but we cite them too rarely in our articles. It is hard to see what a bot-solution would add... Articles consisting simply of a Gold Book link? Gold Book links in articles which give a different definition?

It would be nice to be able to set up a Wikipedia:WikiProject Chemistry/Gold Book workgroup to try to address the editorial aspects, such as making sure that all the relevant articles mention the IUPAC definition in the article text. Unfortunately, this is difficult because of the copyright and database rights over the Gold Book and its electronic form: we cannot (as far as I can see, for the time being) host a list of wikilinked Gold Book topics (even just titles) with assessments etc.

In principle, I am willing to go to Turin to discuss this if it seems worthwhile, but I cannot promise anything at present (not least for financial reasons). In the meantime, it is wonderful to have Beda's interest, especially if it spurs us on to improving things ourselves! Physchim62 (talk) 16:32, 16 May 2007 (UTC)

Great idea, though I'd suggest making this a little broader, perhaps [[Wikipedia:WikiProject Chemistry/IUPAC workgroup? PC, would you be able to take the lead with this? I agree we should just supply links to Gold Book definitions. I think if RSC Pubs can include direct links to Gold Book definitions in its articles, there should be no problem with us getting permission to do this en masse - but the workgroup could make sure of that. I wonder if we might get a nice tool, as is used for DOIs, to do this sort of thing automagically? If the workgroup gets going, I'll do some begging for technical help, there may be a tool on the toolserver that can be adapted for this purpose. Walkerma 17:18, 16 May 2007 (UTC)

Cracked tags

Here's a cracked view of Wikipedia and its prolific use of tags. Hence, in my view, most tags, unless they are of immediate concern, should go to the talk page where they can digest for months at a time without unnecessarily hindering the readability of a good article. --Sadi Carnot 14:26, 2 May 2007 (UTC)

Thanks all for participating in the discussion. I have calmed down especially after reading the cracked tags bit. I like the editorial wisdom page, I will use it next time I encounter a taghappy editor as my countertag. V8rik 19:39, 2 May 2007 (UTC)

Don't worry about it; they are generally overused anyway. I used the following on my userpage:

-) ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 20

13, 2 May 2007 (UTC)

Aw crap, now we're gonna need a DAB page for "DOH" → half-heavy water vs Homer Simpson:) DMacks 20:24, 2 May 2007 (UTC)

50% of Wikipedia American adult readers have college degrees

Here's a good article I stumbled upon today, that might help us decide how we should gauge tag use for science articles and also reader direction. Later: --Sadi Carnot 02:42, 5 May 2007 (UTC)

• 36% of online American Adults Consult Wikipedia - 2007 Pew / Internet Study

The survey is interesting, but of course not all Wikipedia users are adults. ;-) I'm also a bit surprised that 100% of the respondents had a high school diploma or higher. --Itub 06:24, 5 May 2007 (UTC)

RFC for Aldol condensation

Talk:Aldol condensation#Overly technical - concern about accessibility to non-chemist readers FrozenPurpleCube 05:51, 26 April 2007 (UTC)

Interesting 56 page "who coined what in chemistry" reference

I just found this Glossary of coined terms in chemistry. It's pretty interesting and has all the references to the original papers. I skimmed through the first 25 pages and have already found four errors, namely: "free energy" was coined by Hermann von Helmholtz in 1882, the "entropy of the universe tends to a maximum" was coined by Rudolf Clausius in 1865, "molecule" was coined by René Descartes in about 1625, and I'm pretty sure that the specific term "information theory" wasn't used until the 1950s. So use with caution. --Sadi Carnot 04:39, 2 May 2007 (UTC)

Chemistry COTM

The chemistry COTM has rather languished since ~K went on extended wikibreak. I decided to be bold and update it, and it's now Category:Chemistry articles with topics of unclear importance. Please pick an unimportant compound and find a reason for its existence! Current nominations are

• Registration, Evaluation and Authorisation of Chemicals (REACH)
• Catalysis
• Liquid
• Cohesion
• hydroxide/hydroxy/hydroxyl

Please help out, and vote for future COTMs. I'll try to put us back on a monthly changeover. Thanks, Walkerma 06:32, 2 May 2007 (UTC)

I've taken each of the organic compounds on the list and expanded them at least a little bit, except for dichlorobutane, which I sent to proposed deletion - feel free to remove if anyone thinks they can deal with it. I'll leave the inorganic compounds on the list (the much bigger job) to someone else.  :) --Ed (Edgar181) 19:32, 4 May 2007 (UTC)

118 watchlist requests

(cross-posted request from WikiProject Elements) - There's efforts to migrate the element infoboxes into their own sub-templates, so if you're watching the elements, please consider putting the infobox templates on your watchlist as well. (See Wikipedia talk:WikiProject Elements#Watchlist requests for a convenient list of &action=watch links.) Thanks! Femto 12:09, 3 May 2007 (UTC)

Analytical chemistry

I just wanted to inform people here if they are interested that the analytical chemistry article has had some major revisions and I am asking for input on the talk page.--Nick Y. 21:32, 7 May 2007 (UTC)

Sure; when i'm free, i will be sure to add some images on there. ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 21:40, 7 May 2007 (UTC)

I might hold off on that until the article is in a better state. For the most part I actually do not agree with the major changes and would tend to revert but want some input from others as to not discourage editors contributing to the article only to be reverted without any discussion about how to include input in a constructive way. I look forward to some images in the future!--Nick Y. 22:28, 7 May 2007 (UTC)

Carbamate needs references

Looks like something that should be easy to do for somebody familiar with this area. Sancho 23:06, 7 May 2007 (UTC)

Electrovalency

Does anyone here know anything about electrovalency? The article is nearly an orphan, and from what I read there electrovalency is basically a synonym of ionic charge. It seems to me that it is an old term that's not used much by chemists anymore. What should be done with the article? --Itub 11:16, 9 May 2007 (UTC)

I've PRODded it. The term is obsolete to Valence, which isn't looking too healthy itself as a term.... Physchim62 (talk) 11:40, 9 May 2007 (UTC)

Acid-base cleanup

--Belg4mit 11:51, 9 May 2007 (UTC)

Chemical substance

This article is on one of our most basic topics, and a dispute has arisen recently regarding the definition. I greatly expanded the article a while ago (it had been little more than a disambig page) and I consulted a few textbooks to get definitions. Several others, such as User:Beetstra and User:Centrx then did an extensive rewrite, and we achieved consensus. Now User:Hallenrm has argued that the textbook definitions are outdated, and that a chemical substance is best defined as any material object that can undergo transformations responsible for a phenomenon such as a fire or an explosion. Both Centrx and myself considered this wrong, as it implies that a mixture can be defined as a single substance, and we reverted, but Hallenrm believes this unreasonable. Please comment here. Thanks! Walkerma 07:57, 11 May 2007 (UTC)

• Although I could well rate the article, as a non-native speaker, I'll abstain from the very-fine-line discussion. It does make a nice read, both the article as well as the talkpage. Wim van Dorst (Talk) 18:24, 12 May 2007 (UTC).

SMILES entries

SMILES entries in infoboxes are no doubt legitimate and useful, but their normative conventional display as an unbroken (and typically very long) sequence of characters often causes formatting problems in these respective infoboxes. This at the very least causes their respective pages to appear unprofessional, and more importantly it interferes with their ease of reading and use. Please consider adopting some convention (such as the use of break tags and perhaps even explicit indicators ie. [[Wikipedia:SMILES breaks|~]]) to resolve the issue. Regards -Stevertigo 21:44, 17 May 2007 (UTC)

This is an issue that has come up a number of times, but hasn't been fully resolved. Some browsers wrap the text of SMILES without affecting the width of the infobox, while other browsers make the box as wide as the SMILES string (which can obviously be messy). I try to remember to add line breaks to long SMILES structures, and I know that others do also, but it certainly isn't uniform. Does anyone know if there is a way to force the infobox into a certain width, or to force a browser to wrap text? I agree with Stevetigo that we should try to resolve the issue one way or another. --Ed (Edgar181) 11:36, 18 May 2007 (UTC)

I'm not sure that SMILES entries are either legitimate or useful. Who is going to check on Wikipedia to make sure that they have the correct SMILES code? InChI seems to be replacing SMILES for data entry, and this poses a new set of problems for this WikiProject. My PoV is to remove all SMILES lines from Chemboxes. Incedentally, the formatting problem can be easily fixed, but I dont think this addresses the encyclopedic question. Physchim62 (talk) 11:45, 18 May 2007 (UTC)

I can't say that I've ever used a SMILES string from Wikipedia, but if someone wanted to generate a chemical structure from data in the chembox, copying and pasting the SMILES (or InChI) would be easy rather than manually redrawing based on the image. As for which might be more useful, SMILES vs. InChI, as far as I can tell SMILES gets used more often - structure editors (ChemDraw,etc.), online resources (eMolecules.com, PUBCHEM, etc.) seem to favor SMILES. But this is not an area that I have much of experience with, so maybe InChI is replacing it, as you say. --Ed (Edgar181) 12:03, 18 May 2007 (UTC)

The reason for the addition of the SMILES codes was that they allow to paste structures directly into your molecule editor without having to redraw the molecule (no redraw - no mistakes...). This is a big plus, especially for large or complex molecules. While it not always results in the most aesthetic images, it does allow you to check or calculate molecular properties - including the data given in that article. We could add a small script to the site javascript that automatically breaks these lines by insertion of tags without introducing linebreaks, thereby preserving the pastability. Cacycle 02:30, 1 June 2007 (UTC)

I have a suggestion. How about something like {{geolinks-US-streetscale}}, as it appears in White House. So, the smiles should appear on the top above everything else, it can be clickable to search emolecules or something, and it can be pastable. All without screwing up the chembox? --Rifleman 82 06:22, 1 June 2007 (UTC)

I'm not sure we want these things across the top, and if we put SMILES there we still need to resolve the issue for InChI (which can get very long). I think we need something that keeps the SMILES (and InChI) available for a bot or search engine to read, but which is kept hidden from the reader unless they click on something. In reply to Ed, from this recent blog you can clearly see that people do this sort of copy/paste a fair bit (SMILES was the most popular form of search entry). Also see this related thread. I apologise profusely for the duplication of threads, I must've missed the post here. Walkerma 06:55, 1 June 2007 (UTC)

I think we're going to need a toolserver account to run this properly: however, I have a beta-test version of {{InChI link}} up and running. Physchim62 (talk) 08:08, 1 June 2007 (UTC)

Thanks, PC for working on this! I've added that into the anthrone page where we had a broken InChI, we'll see if Google can find the info. I'm not convinced we need to go to an external site, though - I'd rather it just showed the info on Wikipedia. I think we just need something like User:Walkerma/Sandbox3, which I've shown sort-of-working in User:Walkerma/Sandbox4. Unfortunately my technical lack-of-skill means that it looks ugly, and (unlike on the WP:V0.5 page) the shown version is the default instead of the hidden version. Hopefully you get the idea - can Cacyle or PC or Dirk perhaps get this to work properly? Thanks, Walkerma 06:57, 3 June 2007 (UTC)

Conceptually, I like Martin's show/hide InChi box better than a link to an external site. It would be great if something like this could be prettied up and used for both InChi and SMILES, and incorporated into {{chembox new}} (though I feel a bit guilty saying that knowing that I'm asking someone else to do the work, because I would have no clue how to do it myself). --Ed (Edgar181) 13:41, 3 June 2007 (UTC)

My pal from WP:1.0, User:Titoxd, just fixed up my sandbox pages, see User:Walkerma/Sandbox4 to see how it works (the "InChI= above needs removing from the Chembox if we adopt this). We could perhaps have one hide/show box for SMILES and InChI, though transclusion might be tricky for that unless we had one combined SMILES/InChI parameter in Chembox. Do people like this option? Walkerma 04:49, 5 June 2007 (UTC)

Gold Book workgroup

As requested above, I have set up a workgroup as a pilot project to try to improve referenceing of WP articles to the IUPAC Gold Book. The worklist contains 347 articles, that is 5% of the entries in the Gold Book, chosen at random (for statistical and copyright reasons). Feel free to help out! Physchim62 (talk) 07:59, 18 May 2007 (UTC)

I am also working on some links/worklists from the Green Book... Physchim62 (talk) 18:11, 21 May 2007 (UTC)

POLICY DEBATE: Use of source code, mathematical examples and other examples in articles

I have opened a debate on the use of examples in Wikipedia articles (mainly focusing on computer source code and mathematical formulas, proofs, etc.). It seems to me that many examples currently in Wikipedia violate Wikipedia policy, so I believe we need to either clarify or change the situation. Depending on the result of the discussion, this may result in a number of examples being summarily removed from articles!

Please reply there, not here, if you wish to contribute.—greenrd 11:15, 18 May 2007 (UTC)

Chemical equilibrium

There has been some debate going on at Talk:Chemical equilibrium regarding a major re-write of the article. Few people have been involved and there are some major disagreements about the procedure... Perhaps some outside opinions could help. --Itub 11:38, 21 May 2007 (UTC)

move/merge-discussion about Salt

Hello all, there is a discussion on the talkpage of Salt (Talk:Salt) about moving things around with Sodium chloride, edible salt and salt. I am not sure how to answer to it. I'll have a look later, but maybe there should be more people looking at this. --Dirk Beetstra ^{T C} 13:19, 22 May 2007 (UTC)

Chemical principles and Heat and affinity

Paste from Talk:Heat and affinity

Hi, I was thinking that some discussion of the alchemical principles (salt, sulphur, mercury) would be useful to add to the history section of chemical element, or perhaps to history of the molecule. However, I'm not that familiar with this topic, and since the ancient history of chemistry seems to be one of your favorite topics I thought you might know more about it. Cheers, Itub 08:01, 24 May 2007 (UTC).

Yes, I already have most of this typed up in a sub-section called "Heat and affinity" of a chapter called "Affinity and Free Energy" (chapter 11, pgs. 329-368) of a new 2007 textbook on humanchemistry.net publishing soon. I'll just give you the 7-page subsection here: Heat and affinity with the 25-references included and I'll leave it to you to format. Later: --Sadi Carnot 11:02, 24 May 2007 (UTC)

Thanks, I have started doing some formatting. --Itub 13:06, 24 May 2007 (UTC)

Take your time, maybe some Wikipedia:WikiProject Chemistry people can chip in? I'll post a note there. --Sadi Carnot 13:30, 24 May 2007 (UTC)

Unsolved problems in biology nominated for deletion

The article unsolved problems in biology has been nominated for deletion. Your opinion is welcomed at the discussion under Wikipedia:Articles for deletion/Unsolved problems in biology (2nd nomination). You might also have a look at the similar page unsolved problems in chemistry. Cacycle 00:43, 30 May 2007 (UTC)

I'd kill them both off, since to me they appear unencyclopedic. IMHO, such lists represent "scrapbooks", are highly subjective, and are magnets for using WE for original research. Then again, WE has no shortage of disk space and such lists can be stimulating to compile. If they are retained, it might be a good idea to rename these articles "great unsolved problems in ..."--Smokefoot 01:10, 30 May 2007 (UTC)

Kill them off and salt the earth. I have nominated unsolved problems in chemistry for deleteion here. Physchim62 (talk) 09:37, 30 May 2007 (UTC)

• The chemistry article went through a nomination process before (see [2]) and was maintained. The article did not deteriorate since and I see no reason why it should be nominated again (not very democratic). For this reason i will not participate in the deletion nomination procedure The chemistry article is well referenced in the respective pages for at least 5 entries, that should not be a problem. It is a sad sight when 10000 chemists representing an entire science are unable to pinpoint where exactly the unsolved problems are. There are no problems? Well that's just fine, just turn in your research grants, go home and find another profession, job well done. The problem with chemistry is that it is too opportunity driven and not problem-driven. The definition of an unsolved problem?: wherever more than two research groups seem to disagree and publish in the literature, it is that simple (it can be objective!). Lets try to maintain the unsolved articles for all the sciences. The biology page looks crappy but perhaps the Wiki biology people are crappy. In the past I have contributed to On water reaction, Non-classical ion , Hypervalent molecule, Homochirality and Alkane stereochemistry exactly with the unsolved problems article in mind and I was hoping to include Kinetic isotope effect with respect to tunneling and metal aromaticity. I am currently reading up on Atoms in Molecules, a topic that is debated at the moment but I guess will have to wait the outcome of the nomination procedure. V8rik 17:18, 30 May 2007 (UTC)
  • I hope you will vote to keep the article as well, if you feel that it is useful... I stick by my opinion, but I respect yours! Physchim62 (talk) 18:07, 30 May 2007 (UTC)
  • The problem I see with these lists is not that there are no "unsolved problems in chemistry" in general, of course there are plenty, they are the sum of the ongoing research in this field. Many entries, like those listed by V8rik above, are are perfectly valid chemistry topics and good Wikipedia articles. But a valid chemistry topic is not automatically similar to one of those well known "unsolved problems" in mathematics, physics, or philosophy. I think the minimum requirements for an "unsolved problem in xxx" could be the following:
    • It should be well known as an important unsolved problem by everybody graduating in the respective field
    • It should be well recognized by anybody in this field, independent of his subdiscipline
    • It should have traditionally (i.e. over a certain timespan) be referred to as one of the important "unsolved problems" in that field
    • It should not be the "normal" incremental and gradual increase in knowledge we usually see in the natural sciences
    • It should not be just a rephrasing of a subdiscipline in that science

Cacycle 20:55, 30 May 2007 (UTC)

Scientific peer review request

Relative density has been nominated for a scientific peer review: on a quick look, it could do with some cleanup but is factually correct. Physchim62 (talk) 09:48, 30 May 2007 (UTC)

{{cite journal}} and Organic Syntheses

I've made a suggestion at Template talk:Cite journal regarding making citing organic syntheses easy. Perhaps you can drop by if you have an interest in the matter? --Rifleman 82 02:19, 31 May 2007 (UTC)

{{OrgSynth}} is now up and running. If have collected together all the chemistry citation templates I know about and placed them in Category:Chemistry citation templates Physchim62 (talk) 11:22, 31 May 2007 (UTC)

Organocatalysis and WP:COI

There are some conflict of interest issues at this page. Interested parties can take a look at Talk:Organocatalysis. --Rifleman 82 02:51, 31 May 2007 (UTC)

To the person's credit, he has used their full name as a username, so at least he is not trying to be sneaky about this. But I think he has gone overboard on citing himself and his adviser. And the "advantages of" section is also a bit naughty. Walkerma 03:21, 31 May 2007 (UTC)

Elementbox is horrendous

Is there any chance we can turn it into a single template, and just have optional parameters? It's really ghastly having to look at all that in the edit. ♥♥ ΜÏΠЄSΓRΘΠ€ ♥♥ ^{slurp me!} 12:04, 31 May 2007 (UTC)

It's doable, but I would need help. Physchim62 (talk) 16:36, 31 May 2007 (UTC)

User:MZMcBride already converted some articles to the new Template:Elementbox, see [3]/Template:Infobox carbon for example. Documentation and coordination at Wikipedia:WikiProject Elements is lacking though. Femto 18:56, 3 June 2007 (UTC)

Chemspider is notable?

Has anyone heard of, or used, a service called Chemspider? An article was recently created on it, and its deletion is being discussed at Wikipedia:Wikiquette_alerts#possible_COI_at_Chemspider. If you have an opinion on whether this article should be saved, please leave a comment there. EdJohnston 15:32, 3 June 2007 (UTC)

Update: The article was nominated for deletion, but the result was "Keep". ChemSpider is also reviewed in the Digital Briefs section of this week's Chemical and Engineering News. Walkerma 04:54, 12 June 2007 (UTC)

Should we have some notability guidelines for chemical databases to stop this problem from reoccurring? Physchim62 (talk) 16:30, 12 June 2007 (UTC)

Liquid is the Collaboration of the Month for June

Please try and help improve this important but neglected article! Also, please nominate/vote for future COTMs here. Thanks, Walkerma 04:36, 4 June 2007 (UTC)

Mass spectrometry topics

I was glancing at a couple of things for the Gold Book workgroup, and found:

• Mass spectrometry is a very nice article. It's not within my main area of expertise, but I think I'd like to nominate it for A-Class. We don't have a formal place for doing A-Class reviews at WP:Chemistry like we have at WP:Chemicals. Could others take a look and see if they agree it should be A? A-Class means more or less complete, it would just need a bit of cleanup to go to WP:FAC.
• Meanwhile, we don't have an article on molecular ion, which surprises me since much of the little I know about MS is centred around this concept - how it's the highest expected mass in a mass spectrum, and how it breaks apart to give the other ions, how the different MS techniques can affect the amount of it present, that sort of thing. I think there's enough for a whole article - is there anyone here capable of writing such an article? Thanks, Walkerma 16:51, 8 June 2007 (UTC)
• radical ion ? V8rik 16:56, 8 June 2007 (UTC)

I agree that it deserves A class; I see it clearly as a featured article in progress. One thing that might be nice to add are more pictures. --Itub 17:48, 8 June 2007 (UTC)

On the Equilibrium of Heterogeneous Substances

Started monumental paper, please feel free to chip in. Thanks: --Sadi Carnot 15:28, 10 June 2007 (UTC)

Gallium occurence in fly ash - number needs checking

The Gallium article has a statement that the occurence of gallium in fly ash (the solid waste from burning coal) is around 1.5%. That may be a bogus number. Gallium is usually extracted from ores with something like 100ppm of gallium, and if it really constituted 1.5% of fly ash, which is a cheap, easily available waste product, that would be the primary source. So either the number is wrong or the industry is missing a huge business opportunity.

That 1.5% number has been picked up by Slashdot and cited from Wikipedia because of some new developments in GaInAs solar cells. At 1.5% (15,000ppm), there's a business there. At 100ppm, there isn't. So this matters.

That number seems to be from the LLNL periodic table in their kid's section. See Talk:Gallium. --John Nagle 17:14, 10 June 2007 (UTC)

It's a sort-of a true number, though I don't have the paper to hand. From memory: It appeared in a paper around 1938, and it concerned the Northumbrian coal seam (which ran past where I grew up). It suggested that simple ash from the combustion contained significant amounts, but up to 1.5% could be found in the ash that condensed in the flues. In 1982 I actually did some experiments in the lab on this before the coalfield was worked out (I don't think there are any active pits in Northumberland now, though User:Axiosaurus could tell you - he's an inorganic chemist living in Northumberland!). I used fly ash from Blyth power station (now closed), and I found undetectable amounts present - both by isolation (I think it was into ether from 6M HCl extracts - as used in the 1938 paper) and by XRF. I concluded that this was probably because the coal was now burned as a powder, and under the conditions of the combustion the gallium was lost - I think this was discussed in the paper. There are other possibilities: (a) Blyth was burning coal from elsewhere at that point (quite possible) or (b) the ca. 1938 paper got some numbers wrong - but see below.

The ca 1938 paper also described that this same flue dust contained up to 3% germanium. I first learnt about all this stuff when I read in a kids science magazine, "Understanding Science," that Northumbrian coal ash contained germanium, which was extracted out - probably back in the 1950s. They described the whole process used - I seem to recall it involved digesting the ash in NaOH, and it explained about zone refining at the end of the article for purification to make semiconductors. (I still have the magazine in the attic, I can hunt for it if needed). I have also heard anecdotal evidence that this occurred (probably someone like Johnson Matthey). Once silicon replaced germanium, the market collapsed and they stopped extracting the Ge.

So, in summary - the Ga and Ge may be there, but these are only viable as a by-product from the coal combustion. We need to find the ca. 1938 paper (SciFinder, anyone? I don't have access even to decent Chem Abstracts). Northumbrian coal is much less available than before, and you'd have to switch back to 1930s combustion methods to get viable amounts. What may be interesting to investigate, though, is some of the old slag heaps from near old power stations? Walkerma 03:55, 11 June 2007 (UTC)

Coal plants today extract most of the solids from the flue gases with electrostatic precipitators. (It's probably gallium oxide there, with a melting point above 1700C, so it's a solid when it goes through the precipitators.) So even when burning powdered coal, most of the solids are recovered. Modern coal plants produce about 80% fly ash and 20% bottom ash, or slag. I haven't been able to find a reference with a number anywhere near 1.5% gallium for either. I'm finding numbers, but they're much lower:

• 60ppm in coal and fly ash[4]
• 6.45ppm in West Virginia coal [5]
• 275ppm/86% recovery = 320ppm in fly ash "characterized by a relatively high content of Ga and V" at Spanish coal plant [6]

If there was anything around with 15,000ppm of gallium, it should have been noticed by somebody. Commercially, everybody extracting gallium seems to be starting from concentrations of a few hundred parts per million or lower. --John Nagle 04:52, 11 June 2007 (UTC)

A. J. W. Headlee and Richard G. Hunter (1953). "Elements in Coal Ash and Their Industrial Significance". Industrial and Engineering Chemistry. 45 (3): 548–551. doi:10.1021/ie50519a028. gives 0.022 or 0.032 and a maximum of 0.124%.--Stone 07:40, 11 June 2007 (UTC)

I've updated the page to reflect these figures. --Rifleman 82 09:33, 11 June 2007 (UTC)

Cast your vote at the energy article straw poll

A new user turned the energy article into a disambig page; we are trying to fix the problem presently. Please cast your vote at straw-poll overview, on the proposed solution. Thanks: --Sadi Carnot 22:30, 12 June 2007 (UTC)

Cohesion (chemistry)

This article has been submitted for scientific peer review. It is very short and pretty bad. It is part of the Physics Project and the Molecular and Cell Biology Project, but not the Chemistry Project. Is it worth working on or should it just be made a redirect somewhere else. --Bduke 00:35, 16 June 2007 (UTC)

I've seen this term and "cohesive forces" used in non-chemistry contexts. It is usually explained due to "chemistry" without further explanation. I'm not sure that it should really be labeled as chemistry. It is more of a physics concept which of course is rooted in Van der Waals forces, dipole-dipole interactions etc. It is somewhat like coefficients of friction and heat capacities. They are macroscopic properties of materials that are intimately connected to the underlying chemistry. Perhaps we could contribute short summaries and links to the appropriate chemistry articles, but we should not adopt it. I think the article needs to exist since I can not think of an appropriate redirect. Certainly it should not be to any chemistry articles. It is probably visited frequently by 8th graders learning about the meniscus in a graduated cylinder. It is a broad term used in basic science.--Nick Y. 17:31, 18 June 2007 (UTC)

Cohesion is certainly a worthy topic; the great Sir John Lennard-Jones wrote an article about it! :) Lennard-Jones, J. E. Cohesion. Proceedings of the Physical Society 1931, 43, 461-482. --Itub 08:41, 19 June 2007 (UTC)

Miscible: two solvents either are or they aren't ... - right?

As someone who was recently educated on this slightly anal point, I just want to check, that "highly miscible" is redundant. My dictionary says that miscible indicates solubility in "all proportions". I noticed that Miscible states "water and ethanol are miscible in all proportions." The last three words are not needed.--Smokefoot 01:39, 19 June 2007 (UTC)

"In all proportions" is redundant, but this kind of redundancy can sometimes be useful for emphasis or clarity. However, "highly miscible" is meaningless and unnecessary IMO. To answer the question at the heading of this section, well, it depends on temperature. ;-) Many pairs of solvents are miscible only above a critical temperature. --Itub 08:39, 19 June 2007 (UTC)

I agree about the redundancy. But since we're talking about "slightly anal points", wouldn't this article be better titled as miscibility than as miscible - a noun describing the physical property, rather than an adjective? --Ed (Edgar181) 20:12, 19 June 2007 (UTC)

Moving miscible to "miscibility", which is currently a redirect, requires some administrative authority, I think.--Smokefoot 22:54, 19 June 2007 (UTC)

It looks like a good thing to do would be to merge the histories of the two articles. If no one objects, I'll go ahead and do it soon. --Ed (Edgar181) 23:27, 19 June 2007 (UTC)

Maybe I'm stupid, but I had always regarded miscible as meaning simply "mixable", as defined in Encarta or Wordreference.com. I note that in Wiktionary, however, the phrase "in all proportions" has been added - that's news to me. If I am stupid, at least I'm not alone, since a Google search on the bound phrase "partially miscible" gives 73,000 hits in Google, such as this one. I'd always assumed that the term "miscible in all proportions" was reserved for things like methanol + water, whereas "partially miscible" might be applied to things like methanol + hexane (from memory). Maybe I'm wrong, but if there are so many idiots like myself, maybe we need to keep this statement in? Or if we're 100% sure I'm wrong, we should rewrite things to make it abundantly clear to folks like me. Walkerma 04:34, 20 June 2007 (UTC)

(reset indent)I've always understood miscible to be "soluble in all proportions", and that something is either miscible with another thing or it isn't. Yes/no choice. I see this definition in at least here. However, goldbook has mentioned "partially miscible" here. My 2 cents. --Rifleman 82 06:53, 20 June 2007 (UTC)

For me, I think having phrases which qualify the degree of miscibility is important - "miscible" by itself is ambiguous and doesn't say anything about the relative ease of mixing - unless it is assumed a priori that a liquid-liquid mixture is either miscible or not. --HappyCamper 11:10, 20 June 2007 (UTC)

Diethyl ether and water are said to be not miscible. Still, water does dissolve to a couple of percents in ether. So if I mix 1 mL of water with 99 mL of ether, they do mix ... so I would call that partially miscible. If I take 50 mL of water and 50 mL of ether we all know that we get a two-phase system, but it might be 55 mL ether/water mixture and 45 mL of water (I don't know the exact proportions, nor did I do the calculation). So for that, water and ethanol are miscible in all proportions, but for ether and water that is more complicated. Hope this helps. --Dirk Beetstra ^{T C} 11:16, 20 June 2007 (UTC)

This is more complicated than I expected. I have always thought miscibility to imply "in all proportions", and have always heard it used that way. The concept of partial miscibility seems like an oxymoron to me. I wonder if it is a geographical difference, perhaps with European-trained chemists using a less narrow definition. I guess the article should note that regardless of technical definition, in common use it can be applied either narrowly or more broadly. --Ed (Edgar181)

I propose then that we allow "miscible in all proportions" for clarity. But "highly miscible" is too vague and should not be used. --Itub 11:51, 20 June 2007 (UTC)

• Miscibility, as everything in life (and certainly in chemistry) is a matter of amount or grade. Any two given substances never either mix or don't mix. They always mix, albeit to different degrees, depending on the... "miscibility", which is just a term invented to express the concept of "to what degree two substances mix". It is like chemical reactions, where we always get a thermodynamic equilibrium. No reaction can proceed to an exact 100% conversion, and (reversing the direction of reaction) no reaction stays at 0% exactly. The deviations from 100 or 0 could be so small as to be negligible, or even undetectable, though. Just like with miscibility. All substances are partially miscible, if we define "partially" properly. For example, "partially" could mean "in any proportion, and to an extent we can call a complete mixing", and we'd use "miscible in all proportions", or it could mean "only when there is a lot from A and very little from B, or the other way around", and we could say just "partially miscible". — isilanes (talk|contribs) 13:03, 20 June 2007 (UTC)

I disagree on a few points. First, many reactions never reach thermodynamic equilibrium, because they are too slow and therefore don't even happen (at least before the thermal death of the universe ;-). The spontaneous conversion of diamond to graphite is a classic example, although the relatively-long-term existence of any oxidizable or flammable material on Earth is also a good one. Second, when the free energy change of a reaction is large enough you can easily have 100% conversion due to the finite number of atoms in any sample (let's say you have 10^24 molecules and the equilibrium constant is 10^100, for example). Third, there are thermodynamic phenomena that can be considered in all-or-nothing terms, such as those involving critical phenomena. For example, there is a temperature above which solvents are really miscible (in all proportions, if you will), and below which they are not. My opinion is that miscibility is really useful as a term only when restricted to imply "in all proportions". If you use it more loosely you are just talking about solubility, which is certainly a matter of grade. But since it seems that some people really do like to use the term "partial miscibility", I have to concede that adding "in all proportions" is useful for clarity. --Itub 13:23, 20 June 2007 (UTC)

I disagree too. Methanol and water are miscible. I.e., from all proportions 0 % to 100 % methanol in a water-methanol mixture, you will never have two phases. Chloroform and DCM are miscible, THF and water, acetonitrile and water, DMSO and water are miscible. Chloroform can dissolve up to 1 % water; beyond that it separates into phases. It is immiscible. Same goes for benzene/water, toluene/water, water/ethyl acetate. There are some even more interesting combinations like DMSO and hexane, which are likewise immiscible. I think that defining it as a binary yes/no statement is indeed possible. --Rifleman 82 15:02, 20 June 2007 (UTC)

• "many reactions never reach thermodynamic equilibrium, because they are too slow". Agreed, but this is irrelevant. Methanol and water an also not miscible, if the one measuring the miscibility is not a human being, but some entity with a life span shorter than the mixing time (let's say microseconds). I meant to say theoretically or ideally. In practice, you could as well say that methanol and water are not miscible if they are in different pots.

• "when the free energy change of a reaction is large enough you can easily have 100% conversion due to the finite number of atoms in any sample". Agreed again, but this is also irrelevant. It is like saying that the heads/tails distribution of an ideal coin toss is not 50/50 if you flip the coin once, because it will either be 100% heads or 100% tails. Any statistical law or measure (such as thermodynamics) is meaningless without a sufficient number of data. No matter how loaded a die is (how large the reaction free energy), the unfavorable sides will eventually show up, given enough tosses (the unstable reactant will remain, however small an amount, if enough total reacting amount for statistics to work).

• "Chloroform can dissolve up to 1 % water; beyond that it separates into phases. It is immiscible.". Go tell that to the chloroform fraction dissolved into water! For that chloroform, they are miscible. Moreover, it shouldn't be overlooked that when beyond-miscibility amounts of chloroform and water are added together (e.g. 50/50), they do form two phases. But not a "water" phase and a "chloroform" phase. They form a phase of mostly water, saturated with all the chloroform in can dissolve, and a mostly chloroform phase, saturated with water. Pure water and pure chloroform are nowhere to be found.

• It all boils down to what we call "miscibility". Some people argue that solubility is what I mean with miscibility, and that the term "miscibility" should be used only for "ideal/total" solubility. I tend to disagree, because "perfect" miscibility and immiscibility do not exist. For example, a single molecule of solute B will always be soluble in any amount of solvent A, so A and B can not be said to be immiscible. Moreover, at any given tempereature, there will always be a fraction of B solute molecules in solution in solvent A, which form smaller or greater aggregates (microscopic phases), so perfect miscibility is not possible either. However, in the name of non-analness, I'll accept that 0% and 100% mixing can happen, from a practical view, and I'll adhere to the pragmatic last sentence of Itub above: "Miscibility" for "total solubility", "solubility" for "partial solubility", and "in all proportions" any time miscibility is mentioned, to disambiguate it. — isilanes (talk|contribs) 16:00, 20 June 2007 (UTC)

I've already explained my point, and I see it as how isilanes described his view - that he is interpreting miscibility as solubility. I have a few more dictionary definitions to offer: [7], [8]. THere is also a rather strange entry here: [9]. Apart from that, I've nothing further to add.

I think what we should go for is a middle ground of some sort. Why not simply outline what miscibility means in different contexts? --HappyCamper 13:33, 20 June 2007 (UTC)

Apparently the definition is unclear, and we should explain the current interpretations on the page. Dictionaries seem to allow the idea of partially miscible. For my part, the word miscible is useful (and uniquely instructive) only if it refers to the equilibrium state of 100% solubility in all proportions. And 'immiscible' is the condition of not being miscible. Otherwise one should discuss solubility, which does come in high, moderate, and low versions. The notion of complete insolubility, as Isilanes indicates, is a simplification. Thanks to all for the moderate, but incomplete help.--Smokefoot 17:52, 20 June 2007 (UTC)

The Oxford Dictionary of English defines miscible as follows: (of liquids) forming a homogeneous mixture when added together: sorbitol is miscible with glycerol.

Ben 17:51, 20 June 2007 (UTC)

Why use sorbitol, a solid, to exemplify liquids forming homogeneous mixtures??? Is this Oxford Dictionary thing a wiki, so I can fix it?  :) --Ed (Edgar181) 18:23, 20 June 2007 (UTC)

FAR

Alchemy has been nominated for a featured article review. Articles are typically reviewed for two weeks. Please leave your comments and help us to return the article to featured quality. If concerns are not addressed during the review period, articles are moved onto the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Remove" the article from featured status. The instructions for the review process are here. Reviewers' concerns are here. (Yes, I know Alchemy isn't Chemistry but one of the sections touches on modern stuff.) DrKiernan 13:07, 19 June 2007 (UTC)

Class assignment

Just so everyone knows, it seems that a graduate class at UCSD is improving some natural product pages for a class assignment. Since new editors often find Wikipedia frustrating at first, I've invited them to drop by here if they have questions or need help. The article list they are working on is this: Tyrocidine-Bleomycin-Cyclosporin-Doxorubicin-Lovastatin-Lincomycin-Mitomycin C-Ansamycin-Mupirocin-Novobiocin-Thienamycin-Epothilone B-Salinosporamide A-Artemisinin-Vancomycin-Pladienolide

--Ed (Edgar181) 21:14, 19 June 2007 (UTC)

Good ED move and welcome UCSD. There are wikipedia specific issues that may come up that other users may be helpful with. Also in all likelihood part of the purpose of the assignment is about working with others in collaborations and for peer review.--Nick Y. 19:38, 20 June 2007 (UTC)

• Welcome editors. I assessed all the articles for the Chemicals wikiproject. Some have excellent (B-Class) information for the Pharmacology or Drugs wikiproject (not many wikiprojects tags yet), although for Chemicals I most assessed at Start/Mid. Success UCSD students. Wim van Dorst (Talk) 22:08, 20 June 2007 (UTC).

Hermann Arthur Jahn

Translated this new article from the de version. FYI. --Rifleman 82 03:35, 27 June 2007 (UTC)

That's funny, yesterday I created Heinrich Limpricht, also based on the German version. --Itub 11:09, 27 June 2007 (UTC)

Thank your favorite deity for German Wikipedia, where would we be without them?! Physchim62 (talk) 12:05, 27 June 2007 (UTC)

An idea regarding biographies

While looking for information about Heinrich Limpricht (discussed above), I found this website: http://www.scs.uiuc.edu/~mainzv/Web_Genealogy/ . It is interesting because it tells you who was the mentor and who were the notable students of each chemist in their list. Many of the chemist articles in Wikipedia are just stubs, and I think we could enrich them considerably just by adding this very specific piece of information (even the longer articles usually don't mention all the notable students). To make the information more visible and consistent, I would suggest modifying, or creating a modified version of, {{Infobox Biography}} for academics, with the additional fields "mentor(s)" and "notable student(s)" (Note: I just noticed that {{Infobox Scientist}} already does that.) --Itub 12:42, 27 June 2007 (UTC)