Wikipedia talk:WikiProject Chemistry/Archive 18

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Thanks. —

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:

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)[reply]

• 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)[reply
  ]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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

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

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)[reply]

I'm trying to create a

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).[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply

]

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)[reply]

• 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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

There is currently a new taskforce being setted up at

 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)[reply]

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)[reply]

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)[reply]

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)[reply]

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 • 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 • 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)[reply]

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)[reply]

• 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)[reply]
• 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)[reply]
• 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)[reply]

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,

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)[reply]

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

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)[reply]

• 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)[reply]
  • Thanks much. If I tried to fix it myself, it wouldn't be pretty. :) --Moonriddengirl ^(talk) 00:43, 15 April 2009 (UTC)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

Which can be used in sentences like:

Iron nitride{{chemformula}} may be super awesome, but buckminsterfullerenes

{{chemformula}} are clearly even more awesome.

Feel free to tweak the text, and categories, etc...

WP Physics} 21:55, 16 April 2009 (UTC)[reply

]

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)[reply]

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)[reply]

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

WP Physics} 01:04, 17 April 2009 (UTC)[reply

]

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)[reply]

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)[reply]

You can say that of any cleanup template. Why tag with {{

WP Physics} 04:55, 17 April 2009 (UTC)[reply

]

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

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)[reply]

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

I declined the {{

• 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[reply]

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)[reply]

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)[reply]

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)[reply]

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

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)[reply]

See diastereomer.

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

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)[reply]

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)[reply]

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

A college professor I know has a group of students working on improving articles. I provided him with some guidelines from

• 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)[reply]

• 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)[reply]

  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)[reply]

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)[reply]

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

the sole preserve of one or two editors

.

I would like to see

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)[reply]

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)[reply]

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)[reply]

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

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)[reply

]

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

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

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)[reply]

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)[reply]

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)[reply]

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)[reply]

Have no access till monday, but

doi:10.1002/hlca.19600430303--Stone (talk) 20:12, 16 May 2009 (UTC)[reply

]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply

]

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)[reply]

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)[reply]

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)[reply]

Can I add that the data on

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

I don't see what is wrong with the acetone diagram above. Indeed, in the

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)[reply

]

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)[reply]

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)[reply]

I disagree that skeletal formulae are useless for

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.

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

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)[reply]

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)[reply]

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

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

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)[reply]

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)[reply]

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)[reply]

Could someone check the chemistry and health statements in

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)[reply]

Quality!

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

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

Hey guys, I'm currently a member of

• 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)[reply]

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)[reply]

Our

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)[reply

]

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)[reply]

That looks good for a short section. Given the complexity, it might be better to start thinking already about a

summary. Physchim62 (talk) 13:37, 9 June 2009 (UTC)[reply

]

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)[reply]

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)[reply]

WikiProject Chemistry should be the featured WikiProject in next week's

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)[reply]

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

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)[reply]

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)[reply]

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

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

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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

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)[reply]

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)[reply]

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)[reply]

On a closely related topic, I have added a suggestion for naming conventions for name reactions at

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

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)[reply]

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)[reply]

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

Probably that article should be redirected to

Gold saltss. --Smokefoot (talk) 17:28, 23 June 2009 (UTC)[reply

]

Yeah, the

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)[reply

]

A typing error caused me to look for

Ascorbic acid, not the one quoted above. C6H12O6 (glucose) was hit 4733 times. Physchim62 (talk) 13:48, 2 July 2009 (UTC)[reply

]

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))[reply]

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

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)[reply]

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)[reply]

I think the molecular formulas as separate entries are useful (

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)[reply

]

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))[reply]

These redirects don't hurt anyone (except the person that has to add them) and are useful: certainly far more useful that

C2H5OH, 431 hits; C6H6, 1511 hits. These are far higher hit counts than many featured articles! Physchim62 (talk) 13:39, 2 July 2009 (UTC)[reply

]

I think instead of dab pages, they should be

SIA}} template instead of the {{disambig}} template. 70.29.208.69 (talk) 06:25, 5 July 2009 (UTC)[reply

]

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)[reply]

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)[reply]

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

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

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply

]

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

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)[reply]

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)[reply]

So,

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)[reply]

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

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)[reply]

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)[reply]

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

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)[reply]

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

C6H12H6 or C6H12O6? Does that explain it?

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

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)[reply]

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

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)[reply]

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)[reply]

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)[reply]

Sounds good.

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

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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)[reply]

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

I have reviewed