Wikipedia talk:WikiProject Chemicals/Archive 2013

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Category for substances under the Stockholm Convention

How would a category for substances included in the Stockholm Convention on Persistent Organic Pollutants best be named? “Persistent Organic Pollutant under the Stockholm Convention”? --Leyo 23:25, 27 November 2012 (UTC)

I created Category:Persistent Organic Pollutant under the Stockholm Convention. On the other hand, I stumbled over Category:Persistent organic pollutants. I propose this category for deletion, because there is no real definition and the selection of articles in it seems to be arbitrary. --Leyo 15:46, 3 December 2012 (UTC)

→ Wikipedia:Categories for discussion/Log/2013 January 8 --Leyo 16:40, 8 January 2013 (UTC)

Special:ListFiles/Anbrown4

The uploads of this user are mostly of insufficient quality and need to be replaced. --Leyo 21:03, 23 December 2012 (UTC)

Only one was used in project space. I deleted it because it was incorrect and replaced it with a correct version. -- Ed (Edgar181) 15:05, 7 January 2013 (UTC)

Thanks. I nominated two orphaned and incorrect structures for deletion. The remaining ones are used in sandboxes or article for creation subpages. --Leyo 23:11, 7 January 2013 (UTC)

Sodium stibogluconate

The structural formula shown in this article makes us believe that sodium is present in the elementary form. Or am I too nit-picking? --Leyo 16:36, 8 January 2013 (UTC)

I agree, it's confusing. --Ben (talk) 22:14, 20 January 2013 (UTC)

The new one isn't any better, I think. It looks like Na⁺ were bound covalently. Any why it the Sb tetravalent? Or is this a tautomer? --ἀνυπόδητος (talk) 16:57, 21 January 2013 (UTC)

My mistake with the ox state of Sb - will correct soon. Showing Na attached to the carboxylate is convention. I had added a sentence based on a review that in solution the stuff is probably a mixture. No crystal structure has been reported - I looked high and low. Thanks for catching this problem.--Smokefoot (talk) 18:57, 22 January 2013 (UTC)

Links To Both/All Parts of a Chemical

There should be at least somewhere on the page links to the parts of a chemical if applicable (ex. Calcium Sulfate would have a link to calcium and a link to sulfate.). P.S. I think this is where you would put this guide me to the right place if I am incorrect. NanoTechAdvancement (talk) 19:10, 20 January 2013 (UTC)

Usually that's done in the lede, i.e., the opening paragraph or so. Walkerma (talk) 04:47, 21 January 2013 (UTC)

Meglumine antimoniate

Can somebody clarify the formula? The drugbox says it's "variable" and then gives SMILES and InChI. Not sure whether the PubChem structure makes sense. --ἀνυπόδητος (talk) 17:00, 21 January 2013 (UTC)

The drug is complex mixture according to this reference: PMID 9593130. Much of the data in the drugbox seems to correspond to its major component or to a vaguely defined 1:1 complex of meglumine and antimonic acid. I wouldn't say that any of the information is wrong, but it could use some clarification. -- Ed (Edgar181) 17:57, 21 January 2013 (UTC)

Adding a structural formula would facilitate to recognize the structure for lay readers. --Leyo 20:00, 22 January 2013 (UTC)

Bicarbonate

Bicarbonate has been requested to be renamed, see talk:Bicarbonate -- 65.92.180.137 (talk) 05:19, 2 February 2013 (UTC)

I have closed the discussion, declining the move request. Materialscientist (talk) 06:03, 3 February 2013 (UTC)

User_talk:Dy11111#Stop_editing_Chemboxes

I think we've had some difficulty with this Dy11111's edits some time back, and with his IP's edits recently.

This user has requested that he be unblocked. I'm asking that interested editors comment at the link above. --Rifleman 82 (talk) 00:36, 3 February 2013 (UTC)

Mediator

I need a mediator to lift the ban from editting chemboxes. Plasmic Physics (talk) 12:03, 13 February 2013 (UTC)

I am talking to User talk:Plasmic Physics about ways in which the infobox data is derived, and how it is verified, and what may constitute Original Research. Issues for wider discussion on this project are do the infobox elements need references? Is deriving a StdInChIKey and systematicname and publishing on Wikipedia for the first time appropriate, or do we need someone else to have published this before? Graeme Bartlett (talk) 21:49, 15 February 2013 (UTC)

Electron "shells"

When did we arrive at a consensus to include simplistic diagrams like File:Electron shell 092 Uranium - no label.svg in infoboxes? Especially for the heavier elements these seem so highly misleading as to be counter-productive. I would accept these for lighter elements (e.g. sodium) in the body of the article with a warning. Not for anything beyond about argon though. What do others think? --John (talk) 11:35, 17 February 2013 (UTC)

WT:ELEMENTS is a better place to ask. Materialscientist (talk) 11:44, 17 February 2013 (UTC)

Thank you, done. --John (talk) 11:55, 17 February 2013 (UTC)

Plasmic's plans for rewriting the articles on hydrides?

Plasmic physics has been busy revising and creating articles on transition metal (TM) and related hydrides. I recommend that we discuss those plans. My ideas:

• for most TM hydrides, the articles on the hydrides we might consider collecting the material into single articles.
• we should base most content on WP:SECONDARY sources, which (1) is recommended by Wikipedia and (2) helps us avoid problems with undue emphasis on a few specialized sources.

There are probably other ideas on these articles, I am unsure how to solve this puzzle. But we should discuss the theme.

It is disheartening and dismaying to me to see extensive editing being conducted by the single most controversial editor in WikiProject on Chemistry. I accepts that Plasmic desperately seeks to do good and that this activity is probably therapeutic for him, but its seems that we should always discuss big projects. --Smokefoot (talk) 14:42, 16 February 2013 (UTC)

• What articles is this about? The split of iron hydride to iron(I) hydride? --Jorge Stolfi (talk) 21:20, 16 February 2013 (UTC)
• Plasmic Physics is hardly adding any sources, I am adding most of those sources you see. I actually started off the series by writing on iron hydride and chromium hydride, based on their presence in stars, and then included solid phase info in the same articles. Then Plasmic Physics split them into narrower scope articles. I contest that primary sources are inappropriate. I have only used reliable ones. In many cases the supported facts are ones that one source takes from another source, so these would not be undue, but instead supported by more than one researcher. On the topic of splitting off articles, I am neutral on the idea. Originally I thought there was too little material to have separate articles. So I put all information into one. I raised the point that the name iron(I) hydride is original research on the part of Plasmic Physics as no one else uses that name. Graeme Bartlett (talk) 21:52, 16 February 2013 (UTC)

• I see. Well, I am a splitter myself, I believe each compound should be in a separate article. However that does not exclude generic articles on compound families, and "iron hydride" should probably be a generic overview of all hydrides of iron (sort of a disamb page, but with some technical content).
  As for primary vs. secondary sources, I don't think the WP recommendation is relevant to specialized topics that may never find their way into books. Besides, given the way university subscriptions work these days, an editor or a reader can fetch 100 relevant journal articles in a few minutes, even if they are 100 years old; but may be unable to find a relevant book even if he spends an afternoon at the chem library. On the other hand, book publishing has become so casual these days that one cannot assume that a book is more authoritative(*)(**) than 2-3 primary sources.
  As for the three FeH articles, they do seem a bit rough and bloated. The long head sections give the impression that there are tanker convoys laden with iron hydrides cruising the seas. Also methinks there is no need to copy technical data from the primary sources, that interested readers can get from the references with one click; unless the data says something interesting about the compound (e.g. its stability).
  (*) A few years ago, while googling for papers on oxocarbons, I found a book for sale in the Barnes & Noble site (for ₤25) that seemed to be a straight cut-and-paste, down to the last letter, of my own oxocarbon Wikipedia article and a few other articles on specific oxocarbons. 8-)
  (**) One of my (presumably unwelcome 8-) contributions to chemical Wikipedia is lead carbide, a compound that is extremely notable for its apparent non-existence. However I found *one* report, quite probably bogus, of PbC
  ₂ from Pb acetate and calcium carbide in water: and it was in a book, whose author was apparently an expert on the subject...
  All the best, --Jorge Stolfi (talk) 22:56, 16 February 2013 (UTC)

The problem is that combining the iron hydride articles into one generic article implies that they are related. While they are related by the fact that they all contain iron and hydrogen, they are infact two entirely different materials. One is an alloy, or a mixture, separable by mechanical means, and is not a chemical compound by our own definition of an alloy; the others are in fact covalent chemical compounds, separable only by chemical reaction. Combinging the articles, perpertuates the deception created by the scientific community. Plasmic Physics (talk) 01:55, 17 February 2013 (UTC)

• From day one Wikipedia has been divided over the silly discussion primary vs secondary literature (tell me which other encyclopaedia to copy and tell me who will pay for the copyright infringement lawsuit). By splitting these articles I feel Plasmic physics is taking credit for creating articles that he did not start. He should have discussed first. Does Plasmic Physics have access to relevant literature? I wish that anyone taking an interest in editing chemistry pages does have access to a library but unfortunately with many editors this access is lacking. V8rik (talk) 23:14, 16 February 2013 (UTC)

• I checked the old version of iron hydride, just before the split. Splitting seems reasonable, each section had enough material to stand on its own. However I think that the alloy should be split off too, and iron hydride should become again a generic article -- now reduced to little more than the old lead section and one-paragraph summaries of the three sections, with links to them.
  As for the "original research name" Google Scholar gives a hit in this book. Does it count?
  --Jorge Stolfi (talk) 23:53, 16 February 2013 (UTC)

• Also the stuff about iron-hydrogen complexes should be moved back from iron(I) hydride to the generic iron hydride article (or to an article on such complexes, if there is one).
• Electrochemistry of the Iron Group looks to be a suitable source, although I have no access to this to confirm or deny use there! Graeme Bartlett (talk) 01:24, 17 February 2013 (UTC)

The works of Plasmic Physics include editing these: Titanium hydride Titanium(IV) hydride Copper hydride Copper(I) hydride Nickel hydride Iron(II) hydride Chromium(II) hydride Chromium(I) hydride‎ Chromium hydride Zirconium hydride Zirconium(II) hydride Uranium(IV) hydride Mercury(I) hydride Mercury(II) hydride and Binary compounds of hydrogen. Some are his writings and some are splits or renames. My issues have been lack of references, inaccuracies in infoboxes, whether the nonstoicimetric solids should be called an "alloy", non-classical hydrides, and contradictory information about stability. However I am happy enough with what is there at a high level. It is the detailed content that needs improving, no different to our other chemical articles. Graeme Bartlett (talk) 01:40, 17 February 2013 (UTC)

Repeatedly, I have found articles describing the non-stoichiometric solids as alloys, even our own article on interstitial hydrides intrduces the concept. Contradictory information? Tell me, and I'll correct/clarify. I have access to journals, by way of a university subscription. Plasmic Physics (talk) 01:59, 17 February 2013 (UTC)

We already talked about this on your talk page Plasmic. Where the hydride solid has its own crystal form, is it appropriate to call it an alloy? Often there is a ratio where all positions in the structure are filled. Where the amount of hydrogen is very low, eg dissolved, and the normal metallic crystal form is retained, that would sound like the alloy to me. Graeme Bartlett (talk) 03:28, 17 February 2013 (UTC)

By that definition steel is not an alloy, it has its own crystal forms, and many. Plasmic Physics (talk) 05:20, 17 February 2013 (UTC)

I noticed that the the three topics were still somewhat mixed up in the articles. I tried to sort them out; please have a look at these drafts

• User:Jorge Stolfi/Iron hydride
• User:Jorge Stolfi/Iron-hydrogen alloy
• User:Jorge Stolfi/Iron(I) hydride
• User:Jorge Stolfi/Iron(II) hydride

I haven't checked the refs, so I probably mixed some things up, especially in the section about the high-pressure forms of FeHx. If you agree with the general schema, I hope to check that tomorrow. All the best, --Jorge Stolfi (talk) 05:32, 17 February 2013 (UTC)

• Well Iron(I) hydride and Iron(II) hydride are almost unchanged in your forks. (But I have been changing the first independently of your fork. for the overview article FeH₂(H₂)₃ should be in the top pure Fe, H section along with FeH(H₂) previously known as FeH₃. As long as you carried the reference that was attached to the original statements, you should have the references covered. Whether the name "Iron-hydrogen alloy" is the common one is dubious as I find only about a total of 2 independent uses of it on Google, not counting all the Wikipedia mirrors. Your content in the overview and solid/liquid articles looks about the right split. Graeme Bartlett (talk) 07:10, 17 February 2013 (UTC)

• OK. A name I remember from my high school days is "intermetallic compound". Is that still used/appropriate?
  (I though that Iron(I) hydride and Iron-hydrogen alloy should perhaps be joined on the argument that they are just gas and solid phases of the same substance. However the solid is obviously not molecular, and there does not seem to be any evidence that one can be converted into the other without going through the dissociated elements state. And the interested audiences seem to be completely disjoint...)

Titanium hydride I feel is of good quality now. I've been working on it all day, and I'm still going. Plasmic Physics (talk) 08:02, 17 February 2013 (UTC)

This looks reasonable. Do you have a reference for the large paragraph in the intro? Graeme Bartlett (talk) 10:48, 17 February 2013 (UTC)

San-Martin, A. (1 February 1987). "The H-Ti (hydrogen-titanium) system". Bulletin of Alloy Phase Diagrams. 8 (1): 30–42. doi:10.1007/BF02868888. Retrieved 17 February 2013. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

Plasmic Physics (talk) 11:03, 17 February 2013 (UTC)

Why do we have two articles on binary copper hydrides? I tried revising this article based on good sources - hydrides are close to my speciality, but my work was reverted by Plasmic who claims that solid CuH is an alloy and then constructed a tiny article on gaseous CuH. Don't my views count as much as his? What next? Will Plasmic decide to start splitting articles on stoichiometric and nonstochiometric phases of other materials. People remember when he started splitting copper sulfate into its various hydrates? I just think that it is nuts that our least reputable, wacked out editor creates and, because he is willing to invest the time, controls content. Most of us are part time editors, and our work can be readily overridden by those willing to invest the time. We have a fox as the editor in chief of the henhouse journal. The predicament would not be a problem if chemically knowledgeable administrators were more involved, but that is rarely the case because our stalwart admins are busy in real life or just dealing with routine vandalism. But Plasmic being allowed to have such as strong influence on content is completely nuts. Oh well, maybe I need a break. --Smokefoot (talk) 14:14, 17 February 2013 (UTC)

Permission denied, too much work for you to do here. :-) V8rik (talk) 22:18, 18 February 2013 (UTC)

Admins like me, will take action to block people or delete articles, or perhaps close a discussion. Since I am involved here I won't be doing any of that. But Smokefoot, your contribution and opinion is valuable. I suppose we have a splitters versus mergers situation here. Other similar substances could be VO TiO which have a notability as a gas apart from as a solid phase. I suppose many pairs elements will form a diatomic or triatomc molecule only stable as a gas, because if one molecule met another it would react to form the elements. It is good to question whether each needs an article. Graeme Bartlett (talk) 20:38, 17 February 2013 (UTC)

That stance is somewhat ironic, since you yuorself declared to me your intention to create an article on every diatomic observed in extraterrestrial atmospheres. Plasmic Physics (talk) 21:11, 17 February 2013 (UTC)

The articles I have yet to write are the magnesium monohydride and calcium monohydride, both found in stars, and so notable. However I will await the presence of more time and references. There is also a claim of SrF, but I am not convinced of this yet! Graeme Bartlett (talk) 10:44, 18 February 2013 (UTC)

I can only work so fast, perhaps I have spread my resources too thin, but still. Plasmic Physics (talk) 21:14, 17 February 2013 (UTC)

It is more important to pick the bigger topics, such as non-classical hydrides or manganese hydride before the hardly existing CuH molecule. Graeme Bartlett (talk) 10:44, 18 February 2013 (UTC)

I think just the one article on copper hydrides would be best, considering they're not that important. The key points can be summarised briefly. --Ben (talk) 22:09, 17 February 2013 (UTC)

• Just a thought but would it not be an idea to re-name these pages from "'Metal' hydride" to "'Metal'-hydride alloy" to reduce confusion? To me the titles imply stochiometric compounds, alloys are different, after all Iron carbide isn't the same as steel. It may also cause problems if editors make links without checking where they go. Equally, much of the stuff from stars could be safely combined in stellar metal hydrides or some-such, with the possibility to split sections off once they became sufficiently detailed. Project Osprey (talk) 16:10, 19 February 2013 (UTC)

An issue here is that the metal hydride alloy name is hardly used by any other people. Google searches show Wikipedia and its mirrors as dominating the search results, with perhaps only one reliable reference that uses that name. So it is certainly not the common name. Our readers will not be looking for that sort of name. And Project Osprey, you seem to be the first to ever use the term stellar metal hydrides. Graeme Bartlett (talk) 21:09, 19 February 2013 (UTC)

Copper(I) hydride has grown significantly over the last day. Plasmic Physics (talk) 21:48, 19 February 2013 (UTC)

• But where are the references? and where are the edit summaries? V8rik (talk) 22:03, 19 February 2013 (UTC)

I have references on hand, just insert cn templated at the appropriate places, and I'll exchange them with references. I can do nothing about the edit summaries now. Plasmic Physics (talk) 22:14, 19 February 2013 (UTC)

It seems that the consensus emerged - correct me if I am wrong - that copper(I) hydride and copper hydride would be de-split.--Smokefoot (talk) 01:13, 20 February 2013 (UTC)

Not so fast, conditions have changed; give other a chance to respond first. Plasmic Physics (talk) 01:23, 20 February 2013 (UTC)

No, Plasmic Physics, you should slow down. Please, a) could you next time first expand a section and reference it properly, then consider the split. And b) it does not work like this - you're not supposed to put statements in an article, then ask us to put in the 'where do you want a reference'-template, and then you put them. Write and reference at the same time. And still, I hope the references you have are significantly better in showing significance for this compound than the 2 that are now there. Otherwise, even if you have 10 references in the end, if they are all of this quality (and seen that you used these two first does not give me much hope for the next references you have ...) I will still call for a merge, as, simply, even with 25 references this hydride may not notable enough for an own article (as we already suggested months ago).

Regarding the 'metal hydride alloy' .. most of those are just 'solutions' of hydrogen in the metal lattice. I can hardly see the significance in the hydrogen alloy of copper. Some of them may have significance by themselves (palladium!), others again do not. I have to agree with Plasmic that they are not always hydrides, so I don't know if they should be grouped with hydrides, but maybe sometimes they are just not notable enough and we should not even have the article. --Dirk Beetstra ^{T C} 12:53, 20 February 2013 (UTC)

Do we want separate articles on gaseous vs solid inorganics?

A productive discussion might be to explore consensus on separate articles on gaseous vs solid inorganics. My recommendation would be, ordinarily, not to have separate articles on say, gaseous sodium chloride vs solid sodium chloride (or solutions, aqueous sodium chloride does not contain sodium chloride per se). Some of these things exist in the interstellar medium or in various chemical vapor transport or {[MOCVD]] reactors and still other situations. --Smokefoot (talk) 21:43, 17 February 2013 (UTC)

What then of polysilicon hydride v.s. silane, or perhaps hydrochloric acid v.s. hydrogen chloride? Plasmic Physics (talk) 21:56, 17 February 2013 (UTC)

Does anyone think that we should, ordinarily, have separate articles on gaseous vs solid (or molten) inorganics. The term "ordinarily" means that we admit to exceptions (maybe HCl vs hydrochloric) to what I am hoping could be a guideline. Just deciding on this topic would save us future headaches. --Smokefoot (talk) 23:57, 17 February 2013 (UTC)

It seems obvious that we should not. Plasmic Physics, polysilicon hydride has a different empirical formula to that of silane, so they're not really gaseous and solid versions of the same substance. --Ben (talk) 00:12, 18 February 2013 (UTC)

Although there may be circumstances where it is appropriate, e.g. diphosphorus vs. phosphorus. 00:14, 18 February 2013 (UTC)

Neither are iron-hydrogen alloy and iron(I) hydride solid and gaseous versions of the same substance, nor are copper hydride and copper(I) hydride for that matter. Plasmic Physics (talk) 09:22, 18 February 2013 (UTC)

I think that this comes back again to my earlier recommendation regarding these things: take WP:N into account. We are not, and should not want to be, a repository of all possible chemicals. Hydrogen chloride and hydrochloric acid are both separately notable enough, so a good chance for separate articles with all their own properties. Do we need articles for all possible hydrides of iron. No. Some may pass a threshold of notability of their own, the rest can be grouped together in one article. Do the separate allotropes of Sulfur (S8 vs. the polymer) allow for separate articles. That may be quite likely. Other allotropes of sulfur (if they exist) .. probably not. There I would suggest the element page as the conglomerate, and in the section 'allotropes' subsections for ALL reasonably noteworthy (noteworthy is not the same as notable!!!!!) allotropes, and for 'S8' and '(S)n' subsections a one-liner paragraph and a 'main article' link, the others get more in those sections.

But we've been here before (just 4 months ago, and I do not see where this consensus has changed. For that matter, I don't see enough in the Copper(I) hydride that it should not simply be de-split to Copper hydride (the article originally was at Copper hydride (about the solid), Plasmic Physics moved it to Copper monohydride, Plasmic Physics expanded the article to incorporate the CuH-molecule, and Plasmic Physics moved it on to Copper(I) hydride and finally Plasmic Physics split out the original information about the solid Copper hydride back out of it. In my opinion, that split was not discussed, and I think that that split was not in line with that October discussion on Scandium trihydride (in fact: "Scandium hydrides probably deserves a single (thin) article, just like copper hydrides."). The conglomerate of Copper hydrides barely passes notability (but for completeness sake having all 'hydrides', sure), but the two split articles here is plain overkill. That same argument will go for many other stoichiometric/non-stoichiometric compounds (where both exist) or for solid/gaseous compounds with the same stoichiometry (where both exist): One of them has to be distinctively notable before considering to split them out, otherwise make the distinction clear within the article. Splitting them is often the exception.

Plasmic Physics, may I ask you from now on to discuss a split and get independent consensus that a split is necessary before performing such splits. --Dirk Beetstra ^{T C} 09:01, 18 February 2013 (UTC)

I support Dirk's idea of starting a discussion first before a split, since it appears controversial. PS I did create an article on trisulfur a while back. Graeme Bartlett (talk) 10:57, 18 February 2013 (UTC)

I did not know of that allotrope. Interesting one. Well, trisulfur seems quite more defined and much more discussed with relations to known compounds than what I see for Copper(I) hydride. Trisulfur has 17 references, known as a 'stable compound' (as opposed to a strongly transient species with just enough reactivity to react), found naturally in interstellar space, etc. etc. I can clearly see the significance of that compound. I do not see it (yet?) for Copper(I) hydride.

I know that notability is a grey area, but there is a threshold somewhere (though probably not a well-defined one). For me, copper(I) hydride (a total of 2 references pertaining to this compound currently listed, a book chapter telling it is thermodynamic unstable and an article that sees it as a transient species) and ScH₃ are not passing the bar of notability, where S₃ does (the latter likely significantly over 10 references, 17 listed, stable at higher temperatures, observable, 'bulk' spectroscopic data). I think that it is in all our interest to consider that if there are only a few 'lonely' references for a compound that one should consider to keep it somewhere in a broader subject, whereas when there are several (and preferably interrelated) references that one could consider a split (I am intentionally not saying <5 = not notable enough, >4 is notable enough, because I am sure that there will be compounds with 15 references which each just marginally report the compound that hence are not notable, whereas there may be compounds with 1 reference which are). --Dirk Beetstra ^{T C} 11:23, 18 February 2013 (UTC)

Agree: Plasmic Physics should accept discussing potential splits. Agree: Articles on compound classes rather than individual compounds can be effective. Disagree: many unstable or non existing compounds exist that are notable because of the reason they do not exists, no need to sensor them V8rik (talk) 22:15, 18 February 2013 (UTC)

Here are highly specific interpretations of possibly-consensus from above, largely from Beetstra, Ben, and V8rik:

(1) Plasmic Physics is asked to discuss splits before making them.

(2) de-split copper hydride articles. We would mention the unstable CuH diatomic but probably focus more on the condensed CuH.

(3) our MOS would indicate that compound articles will typically not be split regarding gas vs solid materials without consensus.

(4) our MOS would state that articles on nonexistent or unstable species are valid, provided they are notable. (the usual "slippery slope" of notability but we can argue about that on a case by case basis). --Smokefoot (talk) 23:44, 18 February 2013 (UTC)

My two cents:
•A desirable (would not say necessary) condition for splitting is that there is enough encyclopedic contents on each topic to fill more than just one paragraph. Usually that requires a lot more than a fleeting citation in one paper. Theoretical calculations IMHO do not count (unless it is on a *very* interesting molecule like O=C=C=O or icosafluorododecahedrane...)
•Another (almost) necessary condition is that the substances are indeed different and not merely solid/liquid/vapor of the same substance. The split between iron(I) hydride and iron-hydrogen alloy fails this test, but I am willing to let it pass on the grounds that there is no evidence that one can go from the metallic form to the molecular form without dissociation along the way.
•On the other hand, in some cases the split may be better for the readers even if it violates these rules. The question to ask should be, "what is the reader looking for when he gets to this article?" Or: "What will the reader type to the search window when he wants to know about this topic?"
•In any case, methinks there is a broad fuzzy gray area between "must be split" and "must be merged"; we need to have some slack in the system to avoid excessive split/merge entropy.
I haven't checked the copper hydride split (let me recover my breath after the iron one...8-) but I doubt that there is as much material on CuH as there is on FeH...
All the best, --Jorge Stolfi (talk) 00:43, 19 February 2013 (UTC)

Hmm... seems like the overarching policy discussion is contaminated by specific discussions on copper hydrides. Let's agree on the overarching policy, so that we can write it into the MOS first. --Rifleman 82 (talk) 04:33, 20 February 2013 (UTC)

Let the statement be to the effect: We favor broader articles that aggregate several closely related compounds. This statement is especially refers to groups of compounds that are not especially notable, and to compounds that and/or of compounds that are poorly defined. As a direct consequence of this statement, we do not make unnecessary distinctions between compounds in gaseous phase and solid and solution phase.

Support

Support While strict categorization may be intellectually satisfying, we don't want to make information hard to find. An encompassing article is more helpful in this regard. -Rifleman 82 (talk) 04:33, 20 February 2013 (UTC)

Oppose

Oppose/Support Reserved, as "closely related" is a poorly defined qualifier, and it is not clear which articles would be considered as merger candidates. There are only a few TMHs which should qualify under the broadest of interpretations, seeing as how the TM-H alloys are exempt from the above criteria since - they are not compounds: (CrH, CrH₂); (FeH, FeH₂), (HgH, HgH₂). Plasmic Physics (talk) 06:50, 20 February 2013 (UTC)

I will not be able to comment until Monday, as I am shifting to a new address on Thursday, and so will not have access to Wikipedia during that time. Plasmic Physics (talk) 09:35, 20 February 2013 (UTC)

Both There is nothing wrong in having both an article on a family of closely related compounds and also separate articles on some (or all) of those individual compounds. There are plenty of good examples already among the chemistry pages. In some cases (such as liquid nitrogen or charcoal) even individual phases of a compound may deserve articles. The route proposed by Smokefoot is sensible (start with the joint article, and then perhaps split off sections if and when they become substantial enough. But we should not be upset if someone does it the other way. Actually I think it is important to not have any rules on this regard. Each additional rule costs a lot of energy and attriction as people try to enforce it; and ultimately a lot of frustration too, when one realizes that the Rule will never be enforced. I vote for just using common sense on a case by case basis. (And, although I am a sinner myself, I agree with Smokefoot that one should use restraint: Wikipedia is not meant to include every number from every paper, nor to replace professional reference works and databases.)

Jorge - I think most of us fellow sinners agree with you regarding use of common sense in article creation and article splitting. A key word in all of my suggested entries is "ordinarily." I envision that plans for splits would ordinarily be mentioned as a matter of course on the talk page of the parent article. Also, we are not really here discussing normal circumstances, we are discussing some constraints and fervent advice for Plasmic Physics.--Smokefoot (talk) 01:27, 21 February 2013 (UTC)

OTRS ticket 2013022010005232

Folks, we have received an e-mail asking for the hydrogen bromide article to be corrected as follows:

Please amend the density from 3.307 g/dm3 to 3.307 Kg/dm3 (Kg instead of g).

I have no idea whether this is correct, so would someone please look into it and reply here? I will inform the sender of the e-mail that we are reviewing it and send them a link to this page. Thanks very much.--ukexpat (talk) 17:05, 20 February 2013 (UTC)

Hydrogen bromide is a gas. As such, a density of 3.307 g/dm³ is reasonable. But 3.307 Kg/dm³ is much too dense for a gas and is more what you would expect for a liquid or solid. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

gives a value for density at 0 °C of 3.6452 kg/m³ which is the same as g/dm³ or g/L.  This is approximately the same as the value that is currently in the article (the difference may be a result of measurements at slightly different temperature/pressure).  So I don't think the OTRS suggestion is correct.  Since the information in the article is not referenced, I will update it with the 3.6452 kg/m³ value.  -- Ed (Edgar181) 18:11, 20 February 2013 (UTC)

N-Methyl-2-pyrrolidone

This compound has a red X next to its ChEBI link. But as far as I can tell, the ChEBI entry 7307 it links to is for the same compound - the CAS numbers match. Why then the red X? SJK (talk) 12:05, 21 February 2013 (UTC)

I think the bot that normally maintains the verification is not currently running. I have manually verified it and updated the chembox, which should be OK for now. -- Ed (Edgar181) 13:23, 21 February 2013 (UTC)

Template:GHS04

This template is used on several articles. Presumably, one of the templates in Category:GHS templates is the intended one. If anyone can figure out which one it should be, can you create a redirect to it? Thank you. ChemNerd (talk) 20:35, 21 February 2013 (UTC)

14-cinnamyl 3-acetyl oxymorphone

This article has been nominated for deletion. If anyone would like to contribute, the discussion is at Wikipedia:Articles for deletion/14-cinnamyl 3-acetyl oxymorphone. Other newly created articles from the same new editor could probably use some review by chemists. -- Ed (Edgar181) 18:55, 25 February 2013 (UTC)

Related: Wikipedia:Articles for deletion/Iododiphenhydramine. -- Ed (Edgar181) 20:01, 27 February 2013 (UTC)

Alcohol categorization

Hi David. I'm concerned that you are over-categorizing chemical compounds. Could you please discuss your categorization plans first at Wikipedia talk:WikiProject Chemicals? I think it would be best to get consensus before continuing. Thank you. -- Ed (Edgar181) 16:30, 5 March 2013 (UTC)

Well, look at my history and tell me if I'm doing wrong at my Talk page. The categories should be there in my opinion to make it easy for chemists to distinguish alcohols --David Hedlund (talk) 16:42, 5 March 2013 (UTC)

David, the categories you are creating are a huge mess. You are putting articles in categories that don't exist. You are putting subcategories in categories where they don't belong. You are putting parent categories in subcategories, creating a circular categorization. You are even putting category pages in their own category. None of this makes any sense. Please just revert all the categorization you have done. Removing it all will be the easiest way to fix it. ChemNerd (talk) 16:44, 5 March 2013 (UTC)

Since Category:Alcohols is quite highly populated (743 articles currently), it might make sense to introduce some subcategorization. However, it needs to be done in a rational way. The categories Category:Simple alcohols, Category:Higher alcohols, Category:Medium-chain alcohols, Category:Very long-chain alcohols, Category:Long-chain alcohols, Category:Short-chain alcohols, Category:Simple alcohols, and Category:0° alcohols are overlapping, ambiguous, unnecessary, and/or meaningless. I would recommend deleting them all. I'm fine with the new categories Category:Primary alcohols, Category:Secondary alcohols, and Category:Tertiary alcohols. They are reasonable, structure-based subcategorizations. -- Ed (Edgar181) 18:02, 5 March 2013 (UTC)

Support Category:Primary alcohols, Category:Secondary alcohols, and Category:Tertiary alcohols. --Smokefoot (talk) 18:16, 5 March 2013 (UTC)

Can I describe alcohols in their article text this way? Example: "1-Propanol is a short-chain-, simple-, primary alcohol" --David Hedlund (talk) 04:25, 6 March 2013 (UTC)

I agree with Edgar181 that simple structure-based analysis (1°/2°/3°) is fine, but more than that is too much judgement and/or not useful to readers. The short/medium/long is based on an ontology at a site that does not appear to have any verifiability. "Simple" appears to be a completely undefined term. I'm more concerned that even some of the structure-based analysis so far is incorrect. Multiple of the Category:Tertiary alcohols are not tertiary (including neither of your requests in the next section). Before doing any cats, it's critical to know what the cats mean. DMacks (talk) 05:43, 6 March 2013 (UTC)

Tert-Hexanol and Tert-Octanol are tertiary alcohols according to https://pubchem.ncbi.nlm.nih.gov/ Tert-Heptanol was found somewhere else. Can you please have a look and verify that I'm wrong? --David Hedlund (talk) 06:06, 6 March 2013 (UTC)

Verified wrong. As you wrote in the header of Category:Tertiary alcohols: "tertiary ones are RR'R"COH, where R, R', and R" stand for alkyl groups.", which is in agreement with Alcohol#Systematic_names ("based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl (OH) functional group"). The chemicals here are primary because the OH is on a CH₂ group (the end of a straight-chain part of the molecule). This is exactly the reason we use systematic nomenclature for all but the simplest of compounds, rather than trivial names that can be misleading and/or different in different areas of research. For example, here is another tert-hexyl alcohol, that is indeed a 3° alcohol, but here is tert-hexyl alcohol that is a 1° alcohol that has a 3° alkyl elsewhere in the chain. DMacks (talk) 06:40, 6 March 2013 (UTC)

I've never heard of "simple alcohol" and in terms of being short chain, the formula says it better than you or I could. So I recommend dialing back on adjectives.--Smokefoot (talk) 13:06, 6 March 2013 (UTC)

Cerevisterol

I just started this page on a fungal sterol. Could someone knowledgeable please check the chem box; in particular, I'm not sure if my usage of the "Other names" and "IUPAC name" parameters is correct (not sure what the "official IUPAC name is). Thanks, Sasata (talk) 18:12, 12 March 2013 (UTC)

I added an image and stereochemical information to the SMILES, but it looks good to me. -- Ed (Edgar181) 18:50, 12 March 2013 (UTC)

Thanks! Sasata (talk) 19:02, 12 March 2013 (UTC)

The systematic IUPAC name is: (1S,2R,5S,7R,8R,11R,14R,15R)-14-[(2R,3E,5R)-5,6-Dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadec-9-ene-5,7,8-triol. Plasmic Physics (talk) 23:12, 12 March 2013 (UTC)

That name is generated by MarvinSketch, I've checked the name by using text-to-structure translation, and it matches. That being said, I don't know what the prefered IUPAC name is. Plasmic Physics (talk) 23:16, 12 March 2013 (UTC)

Pictures for Titanium hydride

If I post a request for pictures in the talk page, it will most likely get no attention. So, can someone please find a good picture to upload of bulk titanium hydride, preferably of the δ-phase. Here is an example: [1], or [2]. They are from a journal article: [3]. I just need it uploaded, I'll insert it myself. Thanks in advance.

PS We can also use a better image of powdered δ-titanium hydride, the current one is too dark, when compared to other googled images. Plasmic Physics (talk) 12:24, 15 March 2013 (UTC)

Renaming Sulfanyl

I suggest that we rename Sulfanyl. IUPAC has highlighted some problems with systematic naming: take germanyl as an example, according to systematic naming, the molecules [GeH3][SiH2][GeH3] and [SiH3][GeH2][GeH3] produce the exact same name (digermanylsilane). Thus they propose naming the first member of the linear chain germyl instead of germanyl, the following members would not be affected by the change. As a result the two molecules would thus be named digermylsilane and digermanylsilane respectively. Of course they generalised, but here I used germanium as an example. The equivalent for sulfur would be Sulfyl, then Sulfanyl could redirect to a page generalised page on Sulfanes Polysulfanes in the same style as Alkyl redirects to alkane. I'm not suggesting that we rename Sulfanyl to Sulfyl, but some other name seems necessary, perhaps Thiyl? Plasmic Physics (talk) 10:43, 17 March 2013 (UTC)

Hydrosulfuryl? Plasmic Physics (talk) 10:58, 17 March 2013 (UTC)

What is SH called in the literature? Ben (talk) 15:53, 17 March 2013 (UTC)

All of the above and more. Plasmic Physics (talk) 05:35, 18 March 2013 (UTC)

Is one name more prevalent than the others? --Ben (talk) 18:04, 20 March 2013 (UTC)

The title attribute

Mouseover the second image

Names
IUPAC name example
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tracking categories (test):

• SizeSet

I've been putting a lot of images into chemboxes, and I can never be sure what to put into the ImageName parameter (AKA the title attribute), which displays when the user mouse-overs an image. Some people have just put the name of the compound, but that is redundant. A title attribute should elaborate on what's already there, which means it should say what the alt text doesn't.

Recently it occurred to me that I could use it to explain the color scheme for molecular models, since they are there in part to explain the structure to the non-chemist.

I should keep it concise, because many browsers only display the mouseover text for a few seconds. It should just be the symbol of each element, and the name of a color, with an equals sign in between them, separated by commas. For example: N=blue, or mouseover the example to the right. I'd start with the four elements C, H, O, and N in order of importance, followed by the rest in order of atomic number.

Does all this sound alright? If it does, please consider doing this as well.

As a side note for the alt text, I usually just write 'Skeletal formula' or 'Space-filling model'. If I went to the same length to describe the structure as this example (which I grabbed off the template documentation), my job would take about 5 times longer. But if someone wants to edit in alt texts that actually describe the chemical structure, be my guest. Jynto (talk) 10:19, 25 March 2013 (UTC)

"Yes, I would, if I could, I surely would." Plasmic Physics (talk) 12:29, 25 March 2013 (UTC)

Articles with topics of unclear notability from June 2006

All three of the articles at Category:Articles with topics of unclear notability from June 2006 relate to chemicals. It would be nice if somebody could provide a rationale for not deleting them, or simply remove the tags. GeorgeLouis (talk) 04:45, 28 March 2013 (UTC)

I have detagged the lot. Graeme Bartlett (talk) 11:47, 4 May 2013 (UTC)

Does the Chemicals manual of style encourage boring articles?

I have some major concerns that the manual of style used for chemical articles is encouraging boring articles that do not appeal to the lay audience. It, in fact, seems to blatantly contradict the normal standard to have accessible information first, and technical information last. The recommended content for the lead article is almost exclusively technical details that do not interest lay readers (who do not know what an organoarsenic compound is). The sections that laypeople would understand best (uses and history) are recommended for the end. Having "safety" as a standard section would also help make these articles more accessible.

To see what results from this, here is Dioxygen difluoride as I found it several days ago: [4] - while short, it generally complied with the MOS. It had no mention of its extreme explosiveness, it didn't clearly state that it's not found at room temperature. I gave it some much needed repair after learning about this chemical from xkcd. Note that I am not a scientist and have no chemistry training - but sometimes things need a layman's touch. Ego White Tray (talk) 01:34, 13 April 2013 (UTC)

• You make a valid point, however wikipedia is supposed to be an encyclopaedia, so our primary concern is that pages are accurate and of a high quality - we're not really seeking to excite people. As for accessibility to lay readers; this is a different issue entirely. The problem is that chemistry is complex, so technical content will naturally tend to dominate. The best we can do is ensure that pages detailing 'the basics' are written in a manner that anyone can follow. Dioxygen difluoride is not one of those pages, in fact it's probably one of the most exotic chemicals there are. Had xkcd not mentioned it I imagine many people would have gone their whole lives without ever hearing of it (before xkcd the page had about 50-80 hits a day, its now getting ~6000). That said, now that the page is seeing so many lay readers there's probably a case for trying to simplify the wording a little.Project Osprey (talk) 15:57, 13 April 2013 (UTC)
  • I'm not saying remove accurate and high quality technical details. However, WP:UPFRONT is rather explicit that the least technical information should go first, and get more technical from there. The current MOS guide basically does the opposite. Here's an alternative layout:
    • Lede section should give the basic formula and the chemical's appearance and most common applications. If hazardous, the common hazards should be listed
    • Occurrence and production - where it's found in nature and how it's produced
    • Applications/uses - describes in more detail the common uses for this chemical
    • Safety - describes any hazards involved with the chemical
    • History - its discovery and how its uses have changed over time
    • Properties - its classification as a chemical, functional groups, parent molecules, etc. Since this will usually be the most technical, it should be last.
    • See alsos/reference/etc
  • Ego White Tray (talk) 16:59, 13 April 2013 (UTC)

In my opinion, Wiki Chem has higher standards than most parts of Wikipedia so the idea that our MOS deviates is not a concern. Implicit in our approach is that we aim for factual if slightly dry (for nonchemical audience - thrilling for chemists). Most chemical substances are not of broad interest, so it would be unwise (IMHO) to strive too strongly for accessibility with the most of them. My guess (and hit rates confirm) that technical readers are grateful for our current approach.

With regards to the first suggestion above, our current lead section does follow the lines you recommend: classifies the compound, describes basic formula (the empirical formula is in the chembox so we do not repeat that often) gives the substances appearance, common apps, and main hazard when applicable. This part is rather acceessible. It would be strange to describe applications without first describing structure and properties since the core message of chemistry is that applications are linked to properties which in turn are linked to structure/bonding.

The other aspects of the list above have been thrashed around here a lot over the past several years. --Smokefoot (talk) 17:31, 13 April 2013 (UTC)

Actually, the current manual of style says to focus on technical properties first, and maybe mention applications later. Ego White Tray (talk) 18:16, 13 April 2013 (UTC)

Structure and properties is most fundamental to any compound, and should be introduced first. Afterall, it sets the stage for the compound's applications and reactivity. This approach is standard to any common textbook. --Rifleman 82 (talk) 04:39, 5 May 2013 (UTC)

Class project articles

The following new articles appear to be the product of a class project. I've done a bit of minor cleanup, but I will take a closer look shortly. Review by this WikiProject's chemists would probably be helpful considering the quality and accuracy issues that we have had with related articles in the past. Thanks. ChemNerd (talk) 12:50, 22 April 2013 (UTC)

• Imazaquin
• Bromopyrogallol red
• Mezerein

2 articles

Can someone assess these articles for me:

• Tellurium monoxide
• Triphosphorus pentanitride

Thanks. ^King Jakob _C2 11:43, 7 May 2013 (UTC)

The article on tellurium monoxide is complete garbage. Some sort of child's school essay. Axiosaurus said as much on the talk page. Eventually adults will upgrade this article on a obscure material, but in the meantime, a real embarrassment.--Smokefoot (talk) 12:07, 7 May 2013 (UTC)

Considering that one of Wikipedia's major problems is retaining new editors, I'm wondering if the project would be better off without you, Smokefoot. There's a right way and a wrong way to discuss articles, and guess which one you just chose. Ego White Tray (talk) 12:37, 7 May 2013 (UTC)

The one that favors technical accuracy. --Smokefoot (talk) 13:10, 7 May 2013 (UTC)

Smokefoot is not reknowned for his tact and diplomacy, but he is renowned for his accuracy. It is complete garbage - somebody seems to have performed some kind of internet search and then collated the results as an article. It is self-contradictory and largely incorrect. Chris (talk) 21:38, 7 May 2013 (UTC)

I think this is the worst Wikiproject I've ever encountered. This may be the first time that nasty uncivil language towards a new editor was not only defended, but endorsed. Ego White Tray (talk) 00:23, 8 May 2013 (UTC)

I agree that this not a very effective Project, but sadly this not the first time. I have had the displeasure of being at the receiving end of Smokefoot's insult on multiple occassions, and it was indeed defended and endorsed by members of this Project. I still am on occassion. Plasmic Physics (talk) 00:38, 8 May 2013 (UTC)

The Project and its parent are plagued by hypocrisy, bureaucracy, and sometimes, hypocritical bureaucracy. In fact, I still have a bone to pick about a certain ban revocation. Plasmic Physics (talk) 00:48, 8 May 2013 (UTC)

No need to be negative about the project, the project can take on all kinds of people, including critics, finicky people, sloppy people, university students, high school students, experts, gnomes and clueless enthusiasts. Some of us need to learn what comments to ignore, and what actually should have some kind of response. Since we are volunteers, please find out how to enjoy your time in the project. PS I have added a rating. (I should get around to adding C class some time) Graeme Bartlett (talk) 08:55, 8 May 2013 (UTC)

• This is harsh criticism at the expense of a new editor. Too often the enthusiasm exists but access to useful literature is lacking. Do not blame people for not having access to literature except when they are lazy. I would vote for constructive criticism like not use literature from google books older than 40 years. V8rik (talk) 17:00, 8 May 2013 (UTC)

Pethidine3Dan.gif

file:Pethidine3Dan.gif has been nominated for deletion. Does this qualify as {{PD-chem}} ? -- 65.94.76.126 (talk) 07:11, 22 May 2013 (UTC)

Probably a bit too complex for PD. We need Fuse809 to state the license granted. Just because the drawing package is GPL does not mean that anything drawn with it is public domain. If you are Fuse809, please log on to add your license to the image. Graeme Bartlett (talk) 08:02, 22 May 2013 (UTC)

I am not the uploader. Though, this would be autogeneration by systematic creation of a piece of software, wouldn't it be {{PD-ineligible}} in any case? (as how security camera footage is PD-ineligible, as no originality in creation was involved, since it was a pre-scripted routine) Or is there more originality (term of art) attached than I'm supposing in this case? -- 65.94.76.126 (talk) 05:56, 23 May 2013 (UTC)

C class

I have created the C class category, it has appeared now in the autogenerated lists of article quality. Wikipedia:WikiProject Chemicals/Qualityscale describes the quality, and if you have any Chemical specific text to add there that is welcome. Graeme Bartlett (talk) 22:00, 24 May 2013 (UTC)

Chalk

There seems to be some confusion about magnesium compounds and their uses at chalk (disambiguation), chalk (drying agent), talc and maybe magnesia. Any takers? Globbet (talk) 01:39, 29 May 2013 (UTC)

Twofold dioxirane?

Carbon tetroxide is stated to be a twofold dioxirane in both these articles. Since CO₄ has a four-membered ring, it is not a dioxiran per se, and I have some doubts if this term is meaningful at all. Can someone please explain me what it means? Thanks, Szaszicska (talk) 06:30, 25 May 2013 (UTC)

It seems to be a mistake, it's not 'twofold' of anything, or an oxirane for that matter. It is an oxetane (trioxetane), with the IUPAC name: 1,2,3-trioxetan-4-one. Plasmic Physics (talk) 03:01, 26 May 2013 (UTC)

I agree and simply removed the incorrect statement. -- Ed (Edgar181) 13:11, 30 May 2013 (UTC)

Perhaps the editor was thinking about twofold-lactones, also known as cyclic carbonate esters, when they wrote the sentence, and just forgot what they were writting mid-sentence? I guess you could call it oxygen carbonate if you're that way inclined or even lactone of hydroperoxy hydrogen carbonate. Plasmic Physics (talk) 13:55, 30 May 2013 (UTC)

Plasmic: Flicking through the revision history I see that 'twofold dioxirane' is mentioned before the image is included. So I suspect whoever wrote it thought the structure was 1,2,4,5-tetraoxa-spiro[2.2]pentane, which is CO₄ arrainged as a twofold dioxirane. Project Osprey (talk) 14:33, 30 May 2013 (UTC)

That makes much more sense. It means it comes down to erroneous OR. Plasmic Physics (talk) 22:39, 30 May 2013 (UTC)

Talk:Organic_semiconductor#Organic_semiconductor.23Merger_proposal

There is an ongoing discussion at Talk:Organic_semiconductor#Organic_semiconductor.23Merger_proposal over merging organic electronics into organic semiconductor. I thought that it may be of interest to your WikiProject. --Rifleman 82 (talk) 15:48, 30 May 2013 (UTC)

FAR

I have nominated Acetic acid for a featured article review here. Please join the discussion on whether this article meets featured article criteria. Articles are typically reviewed for two weeks. If substantial concerns are not addressed during the review period, the article will be moved to the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Delist" the article's featured status. The instructions for the review process are here. FutureTrillionaire (talk) 19:57, 30 May 2013 (UTC)

New article request

It would be useful to have an article on Oxidanium tetrahydroxyborate. It is the active component in solutions of Boric acid, yet it is only touched on in the Boric acid article. I'm unsure whether this chemical compound is isolable, but that is hardly a factor; I have seen many articles on such compounds that have only been encountered in solution. Plasmic Physics (talk) 00:20, 29 May 2013 (UTC)

(https://en.wiki.x.io/w/index.php?title=Wikipedia_talk:WikiProject_Chemicals&diff=557509124&oldid=557267434) !--122.109.117.224 (talk) 11:49, 1 June 2013 (UTC)

(edit conflict) My mistake, I got confused when I checked the edit history. All is restored now to its original state. We could call it oxonium. Oxidanium is however the current IUPAC name, but I know that Wikipedia is not keen on following standards, and is more like a stew of popular opinion. In any case, what we name it, is secondary to the suggestion. Firstly, I need to establish whether such an article, whatever it is called, is in fact useful. I posted it for a second opinion. Plasmic Physics (talk) 12:05, 1 June 2013 (UTC)

Hydroxonium tetrahydroxyborate?--122.109.117.224 (talk) 08:33, 2 June 2013 (UTC)

Trihydridooxygen(1+) tetrahydroxidoborate(1-)? Plasmic Physics (talk) 08:37, 2 June 2013 (UTC)

Or even aquahydrogen(1+)...? Plasmic Physics (talk) 08:40, 2 June 2013 (UTC)

Trihydroxidanium tetrahydroxyborate?--122.109.117.224 (talk) 10:41, 2 June 2013 (UTC)

That would be superfluous - unsubstituted oxidanium has three hydrogens attached. It would be like saying tetrahydromethane instead of methane. 'Oxonium' is the pre-2005 substitutive algorithmic IUPAC name, so an element under a domain. 'Trihydrooxygen' and 'aquahydrogen' are the pre-2005 additive names, and elements under the same domain. 'Tetrahydroxyborate' is an element of the intersection of the two domains. So under pre-2005 nomenclature algorithms, only the terms 'oxonium tetrahydroxyborate', 'trihydrooxygen tetrahydroxyborate', and aquahydrogen tetrahydroxyborate are viable solutions. Under post-2005 algorithms the following three solutions exist: 'oxidanium tetrahydroxyboranuide' (substitutive), 'trihydridooxygen(1+) tetrahydroxidoborate' (additive) and 'aquahydrogen tetrahydroxidoborate' (also additive). There is yet another post-2005 additive solution, but it is too unconventional: 'μ₃-oxidotrihydrogen(1+) tetrahydroxidoborate'. Plasmic Physics (talk) 12:07, 2 June 2013 (UTC)

Trihydroxonium tetrahydroxyborate? 122.109.117.224 (talk) 12:32, 2 June 2013 (UTC)

Same problem as with the one above, superfluously added hydros. Plasmic Physics (talk) 22:58, 4 June 2013 (UTC)

No 122.109.117.224 (talk) 05:32, 5 June 2013 (UTC)

'No' to what? 'nd why yell? Plasmic Physics (talk) 11:18, 5 June 2013 (UTC)

Deuterium vs Hydrogen? = Distinguish — Preceding unsigned comment added by 122.111.251.68 (talk) 16:33, 7 June 2013 (UTC)

So normally you would be about 99.98% correct 122.111.251.68 (talk) 17:22, 7 June 2013 (UTC)

Is there anything to say about it that is different from what one would say about boric acid, or is it just the technically correct way of identifying its solvated form? DMacks (talk) 09:54, 2 June 2013 (UTC)

Sorry DMacks :-( --122.109.117.224 (talk) 11:05, 2 June 2013 (UTC)

It is chemically distinct from boric acid - boric acid is highly insoluble in water, only solvating by forming a weak adduct (BH
₃O
₃H
₂O) under extraordinary conditions. However, as a Lewis acid, it is moderately reactive with water, to produce the distinct chemical species BH
₄O⁻
₄, and the H
₃O⁺
ion. Apparently, it is possible to coprecipitate H
₃OBH
₄O
₄ at cryogenic temperatures. Plasmic Physics (talk) 11:07, 2 June 2013 (UTC)

Short answer = NO 122.109.117.224 (talk) 11:32, 2 June 2013 (UTC)

What do you mean "No"? It's more than a technicality, it's not a matter of solvation. Plasmic Physics (talk) 12:13, 2 June 2013 (UTC)

Purification of Boric Acid = Recrystallize from Dihydrogenoxide 122.109.117.224 (talk) 12:47, 2 June 2013 (UTC)

No need to be snide. Chemical equilibrium does not imply solvation. Plasmic Physics (talk) 12:52, 2 June 2013 (UTC)

Bradykinin#Physiological Role (Function)

Can someone please check the validity of the statement "Bradykinin is a potent endothelium-dependent vasodilator, causes dilation of non-vascular smooth muscle" I'm dealing with an OTRS query that it causes contraction not dilation of non-vascular smooth muscle. Thanks. NtheP (talk) 17:11, 4 June 2013 (UTC)

Fixed. Why not ask at WT:PHARM in the first place? ;-) --ἀνυπόδητος (talk) 08:01, 8 June 2013 (UTC)

Request diagram of cubic fluorine

Could I please get a diagram made of cubic fluorine? The reference from ~1970 (I think by Pauling) has a nice one, but I presumably can't just cut and paste. Not sure what perspective to use and if you want to show the molecules "wiggle" like he did. But in any case...please draw me something. Will go in the subarticle, "Phases of fluorine", and perhaps in the fluorine article itself (less likely though).TCO (talk) 15:20, 11 June 2013 (UTC)

File:Beta-fluorine.png. Materialscientist (talk) 00:27, 12 June 2013 (UTC)

XKCD again...

The latest XKCD: what if strip has highlighted the fascinating yet obscure chemistry of furanocoumarins. There's been a predictable surge in visitors to that page and baring in mind that there were a lot of edits to dioxygen difluoride was that was mentioned it may be an idea to keep an eye of that page for the next few days. — Preceding unsigned comment added by Project Osprey (talk • contribs) 19:27, 13 June 2013 (UTC)

Deoxyinosine monophosphate

Would somebody please check this out? It was speedy-tagged as {{db-talk}} because it was submitted on the talk page by IP 137.205.171.220 (talk · contribs · WHOIS), but I have moved it to be an article as it looks OK. The IP is registered to Warwick University. I will suggest that they register an account. JohnCD (talk) 14:46, 21 June 2013 (UTC)

It's now a reasonable stub, wikilinks included, etc. EdChem (talk) 15:08, 21 June 2013 (UTC)

New article: Baralyme

Published to main namespace from AfC. Feel free to improve it; it could use the addition of more refined categories, if available. Northamerica1000^(talk) 09:32, 22 June 2013 (UTC)

Another new article: Atraric Acid

From AfC. Feel free to improve it. Northamerica1000^(talk) 09:54, 22 June 2013 (UTC)

I've added the systematic name, which is methyl 2,4-dihydroxy-3,6-dimethylbenzoate. It's a fairly straight-forward structure to draw for someone with the appropriate software. EdChem (talk) 11:22, 22 June 2013 (UTC)

There was already a diagram of it in several formats on commons (found by searching for its name there), so I added it to the article along with some other basic infobox items. Although someone with some svg knowledge might want to clean it up (or redraw it from scratch)--the bonds are a bit uneven and the lack of margin makes it appear cut off in some places. DMacks (talk) 15:00, 22 June 2013 (UTC)

Thanks, I should have thought to look on Commons. EdChem (talk) 00:38, 23 June 2013 (UTC)

d:Wikidata:Property proposal/Term#Chemistry / Chemie / Chimie

I think it would be good if also members of this project would contribute in this discussion/poll on Wikidata since it indirectly also affects the articles here. --Leyo 12:13, 24 June 2013 (UTC)

Deletion discussion

The new article Hongdoushans has been nominated for deletion. Please consider contributing to the discussion at Wikipedia:Articles for deletion/Hongdoushans. -- Ed (Edgar181) 14:26, 26 June 2013 (UTC)

"Unacceptable Levels" (film)

Someone may wish to start a Wikipedia article "Unacceptable Levels" about the documentary film of the same name.

• Unacceptable Levels - Pollution just got personal: a new movie | Jennifer Sass's Blog | Switchboard, from NRDC (June 18, 2013)
• About | Unacceptable Levels
• Unacceptable Levels

—Wavelength (talk) 04:53, 6 July 2013 (UTC)

Cluster.jpg

image:Cluster.jpg has been nominated for deletion. The 2007 version of the file is a selenite crystal. -- 76.65.128.222 (talk) 04:33, 9 July 2013 (UTC)

Thanks. As a quick fix, I have transferred the original selenite upload to File:USFWS selenite.jpg, declined speedy, and moved this file to File:Galaxy cluster Abell 2218 gravitaitonal lens.jpg. Materialscientist (talk) 04:56, 9 July 2013 (UTC)

Residue (chemistry)

should be splitted into Residue (chemistry) and residue (molecular biology) since everything after "In biochemistry and molecular biology, a residue ..." is definitely totally different from the rest!.--141.58.45.38 (talk) 11:59, 7 August 2013 (UTC)

You raise an interesting point, but it doesn't really fall within the WP:PHYSICS realm of interest. I would suggest starting a discussion on Talk:Residue (chemistry) and then asking participants in WP:CHEMS and WP:BIOLOGY to comment. Personally I agree that the two definitions are essentially separate, but I don't think there is enough out there talking specifically about biochemical/molecular bio residues to warrant its own article - a simple definition would be in violation of WP:DICDEF. It seems, on the other hand, that there is enough material for an article on chemical residues. Corvus coronoides _talk 13:08, 7 August 2013 (UTC)

Moved here from WikiProject Physics --141.58.45.38 (talk) 15:22, 7 August 2013 (UTC)

Theaflavin digallate

There are some questions at Talk:Theaflavin digallate about the chemical structure and ChemBox data in Theaflavin digallate. Input from other chemists would be appreciated. Thank you. -- Ed (Edgar181) 15:27, 9 August 2013 (UTC)

Fetish categorizers are at it again

Do we really sanction the creation of so many new highly specialized categories. Example: "removed Category:Acridines; added Category:Quinoacridines" --Smokefoot (talk) 12:38, 12 August 2013 (UTC)

This reminds me... Salicylaldehyde was recently added to 'Category:Phenolic compounds found in castoreum', which is itself a sub-subsection of 'Category:Chemical compounds found in castoreum'. I'd of done something about it sooner - expect I saw it on my way to bed and then forgot all about it. Project Osprey (talk) 13:27, 12 August 2013 (UTC)

That's funny, because I notified the Chemistry Project a while ago about these highly specific categories, and no one so much as breathed my way. Plasmic Physics (talk) 14:00, 12 August 2013 (UTC)

It's a recurring problem, so I guess sometimes people get tired of dealing with it. -- Ed (Edgar181) 19:40, 12 August 2013 (UTC)

I've left a warning for User:حسن علي البط ‎ who has been blocked in the past over this issue. -- Ed (Edgar181) 19:40, 12 August 2013 (UTC)

Fluorodeoxyglucose vs Fludeoxyglucose - WP:MEDMOS vs WP:COMMONNAME

Please consider commenting over there. -- Scray (talk) 06:53, 15 August 2013 (UTC)

New pages everywhere

Someone might want to keep an eye on Special:Contributions/Jatlas who seems to be creating new pages by the boat-load. I'm not sure if they're wrong or against the rules per se but they are all stub-class (if that) with minimal to non-existant referencing. Project Osprey (talk) 12:33, 16 August 2013 (UTC)

Well you might invite or encourage him to disclose his plans and tell him that experienced editors can offer advice. And, dare I say, encourage him to follow WP:SECONDARY. This guideline is invaluable in these cases (frenetic generation of content) as it induces such editors to establish impact, salience, or even mild notability. --Smokefoot (talk) 13:04, 16 August 2013 (UTC)

Incorrect structural formulae in Novobiocin

User:Stefanobiondi notified me of incorrect formulae in the article Novobiocin. In figures 1 and 4, the allyl chain is missing one CH₂ unit. The error has been in the article for 5 years. Could someone who is skilled in reaction mechanisms check these figures for additional errors and correct them? --Leyo 20:39, 18 August 2013 (UTC)

RfC: Should Roundup (herbicide) be un-merged from glyphosate?

See Talk:Roundup (herbicide)#RfC: Un-merge from Glyphosate?

Thank you. Binksternet (talk) 23:13, 20 August 2013 (UTC)

Period 1 electron distribution

• image:Electrons distribution of Helium(He).png
• image:Electrons distribution of Hydrogen(H).png

have been nominated for deletion (these will not appear on article alerts, since they are not FFD nominations) -- 76.65.128.222 (talk) 08:47, 26 August 2013 (UTC)

Category:Chemical structures

I moved all chemical structures in this category to Commons except of the four orphaned ones. What shall be done with those? Is there a use for them? Or may they be nominated for deletion? --Leyo 17:22, 6 September 2013 (UTC)

I think you can move them in Commons:Category:Chemical reactions or other related categories. --Daniele Pugliesi (talk) 22:38, 16 September 2013 (UTC)

I know I can, but there must be a reason why they are orphaned. If they are incorrect, they should get deleted, not moved to Commons. --Leyo 08:04, 17 September 2013 (UTC)

I don't know neither. Try to ask on Wikipedia talk:WikiProject Molecular and Cellular Biology also. --Daniele Pugliesi (talk) 12:31, 17 September 2013 (UTC)

If I remember correctly, the editor that uploaded those images was adding text with significant copyright violations to articles along with these images. So the entire edits were removed, causing the images to be orphaned. I don't think there is anything wrong with the images themselves, though - they look fine to me. -- Ed (Edgar181) 18:03, 17 September 2013 (UTC)

I have now moved the remaining images to Commons. IMO the category can get deleted. There is only one subcategory and one article in it. --Leyo 12:31, 26 September 2013 (UTC)

New articles

As in the past, I will be working with young chemists to create new articles in Wikipedia, and hopefully allow them to learn some basic chem. The focus is on content, not on formatting for Wikipedia. So my proposal is to spare them the hassle of registering and the vetting that comes with a new editor's first article. Instead, I propose to create short articles (almost empty chembox, ref section, some categories). The students would then edit/expand these articles, soon after their creation. The articles we will create will be thinner than we have done in the past. But later in the year we hope to tackle more complex projects including article improvement. Please let me know if you see problems. Thanks, --Smokefoot (talk) 17:21, 17 September 2013 (UTC) Here we go:

• Phanephos (esoteric but nifty structure), isovaleraldehyde (biodegradation of leucine), Bis(dinitrogen)bis(dppe)molybdenum(0) (first Mo N₂ complex), Chromium(III) iodide (one of the last stable binary halide left), Tetrabutylammonium hexafluorophosphate (important to echem, I wish this article were stronger), Hexachlorodisilane (reagent for deoxygenation of phosphine oxides), Co4(CO)12 (nearly complete on major binary carbonyls), TiSe2, MoSe2, silicotungstate (improve slightly), 1,1,1-Tris(aminomethyl)ethane (another tripod ligand),

I'm glad that you are doing this with your students. I think it is good to have young chemists introduced to the way that Wikipedia articles are written. I can't remember if you have done this in the past, but I would suggest creating new articles first as drafts in userspace and have the students work on them there. Then when you and the students are satisfied with the articles, they can be moved to proper titles in article space. -- Ed (Edgar181) 17:57, 17 September 2013 (UTC)

Mercury nitride

Is the chemical structure correct? I would guess that N–Hg–N is linear. --Leyo 20:41, 27 September 2013 (UTC)

This article was revised to reflect my best understanding of the topic, which is barely notable. --Smokefoot (talk) 22:14, 5 October 2013 (UTC)

class article

Request stub started for the class of silicon fluorides.71.127.137.171 (talk) 00:07, 6 October 2013 (UTC)

Never mind, there is one on polysilicon halides. Good enough.98.117.75.177 (talk) 16:44, 12 October 2013 (UTC)

Amphetamine verified drugbox fields

I'm not entirely familiar with the identifier verification system, so I was wondering if anyone from this wikiproject would be able to validate the links in this article, as they seem to go to the correct place. I intend to nominate the article for FA status very soon, and I have a feeling a bunch of N marks in the drugbox won't help my cause in the review process.
Thanks in advance, Seppi333 (talk) 02:00, 14 October 2013 (UTC)

RFC on Elements infobox

Hi chemists, please stop by this RFC on modifying the icon images in the Elements Infobox: [5]

208.44.87.91 (talk) 01:01, 15 October 2013 (UTC)

Wikipedia:Categories for discussion/Log/2013 October 31#Category:Persistent pollutants

FYI: I nominated this new category that is not well defined for deletion. --Leyo 10:32, 31 October 2013 (UTC)

Periodates

Hi all, I'm concidering doing some work on the periodate pages but before I start I'd like to get some opinions on the page layout. Periodates exist in two forms: metaperiodate IO₄⁻ and orthoperiodate IO₆⁵⁻. Currently these two forms are grouped together on each page, which creates something of a confict in terms of Chemboxes (currently they just consider the meta form) and makes the content a little tricky to organise. The simplest solution is just to leave the layout as it is; the other option would be to page-slip to give meta and ortho pages for each common name. Splitting would make sence if we ever have pages on compounds that only exist in the one form (e.g. sodium hydrogen periodate, Na₃H₂IO₆) but will obviously lead to a lot of disambiguation pages. Does anyone have any thoughts/opinions about all this? Project Osprey (talk) 12:53, 1 November 2013 (UTC)

Great idea to tackle this complicated theme. Since you are collecting suggestions, one approach would be to upgrade the current article to present bare facts on the various forms ranging from IO6 to IO5 to IO4 and perhaps some condensed species (as listed in Greenwood and Earnshaw). With those basic facts under control. my approach would be to focus on articles on the single most important compounds, not anions, illustrating the various classes. We did that with bis(triphenylphosphine)iminium chloride and tetraphenylphosphonium chloride, instead of articles on the cations bis(triphenylphosphine)iminium and tetraphenylphosphonium. Sodium periodate for example needs help. Good luck. --Smokefoot (talk) 13:16, 1 November 2013 (UTC)

Just checked Chem Abs for "periodate": 23000 references, including 190 items classified as reviews and books (most are not or have never been cited). It appears that the main app is in carbohydrate chem for scission of diols, e.g., "Periodate oxidation of polysaccharides for modification of chemical and physical properties" Kristiansen, Kare A.; Potthast, Antje; Christensen, Bjorn E. Carbohydrate Research doi:10.1016/j.carres.2010.02.011. Checking Encyclopedia of Reagents for Organic Synthesis, six periodates are listed, but only sodium periodate seems to be widely used. --Smokefoot (talk) 17:58, 1 November 2013 (UTC)

A few discussions you might want to take part in

There are a few periodic table-related discussion being held at WT:ELEMENTS. You might find them interesting.

one -- how to color elements that can be considered a part of more than one categories: should those cases be shown on a table, should we change nonmetal categories, etc.

two -- what table use in an infobox of a chemical element: 32-column one (we have now) or 18-column one (we might switch to).

three -- should we switch to rare earth metals category instead of lanthanides we have today?

Please take part--R8R Gtrs (talk) 17:44, 19 November 2013 (UTC)

A few discussions you might want to take part in

There are a few periodic table-related discussion being held at WT:ELEMENTS. You might find them interesting.

one -- how to color elements that can be considered a part of more than one categories: should those cases be shown on a table, should we change nonmetal categories, etc.

two -- what table use in an infobox of a chemical element: 32-column one (we have now) or 18-column one (we might switch to).

three -- should we switch to rare earth metals category instead of lanthanides we have today?

Please take part--R8R Gtrs (talk) 17:45, 19 November 2013 (UTC)

Methylene (compound)

Someone might care to take a look at methylene (compound)- it has been heavily edited since March 2013. It contains an amphotericity statement that is very similar to sections in gallane, mercury(II) hydride and iron(II) hydrideAxiosaurus (talk) 08:35, 31 October 2013 (UTC)Sorry I hit a disambig. link with methylene, I have corrected this post to methylene (compound), it refers to CH₂.Axiosaurus (talk) 09:35, 31 October 2013 (UTC)

Correct me if I'm wrong, but if its amphoteric it can accept or donate a pair of electrons; carbenes on the other hand accept and donate pairs of electrons, normally simultaneously and to/from the same subtrate. This to me is subtly different. I've seen carbenes described as double radicals or as having both a + and - charge, but never this. Seems like WP:SYN to me. Project Osprey (talk) 08:55, 31 October 2013 (UTC)

Another example of the damaging influence of Plasmic Physics. Really unfortunate.--Smokefoot (talk) 13:26, 31 October 2013 (UTC)

None of the sources I checked for Hg or Fe hydrides were saying they were amphoteric, so. It's original research or possibly a synthesis bu Plasmic. The refs were talking about complexed stable derivatives of the hydrides, but the sections tried to make out the statements applied to the pure hydrides. I would delete the whole section, or else make it reflect what the refs say with no extrapolation or synthesis. Graeme Bartlett (talk) 10:57, 1 November 2013 (UTC)

now after checking the ref given for methylene, it is really about diazomethane, a different molecule, so lets remove that section. Gallane amphotericity is totally unreferenced, so likely wrong too. Graeme Bartlett (talk) 11:39, 1 November 2013 (UTC)

Due to lack of any support for the text here, I have removed it. Graeme Bartlett (talk) 11:36, 22 November 2013 (UTC)

Wikidata

I know that your project is working on chemicals data since a long time now, but I just want to say that Wikidata is starting to import data at large scale in order to offer chemical data to all wikipedias. If you have comment, ideas or want to take part at this action please visit d:Wikidata:WikiProject_Chemistry and d:Wikidata:WikiProject_Chemistry/ChemID. Snipre (talk) 09:47, 8 December 2013 (UTC)

MSDS links

http://physchem.ox.ac.uk/MSDS was a website collection of MSDS pages. It no longer exists (just a notice that the whole site was taken down in December 2011). We have lots of links to it that need to be replaced or scrapped. I'll hopefully have time in the next few days to scrap them (we have "External MSDS" or similar infobox items), so this is sort of a reminder to myself here. But also a central notice about what the situation is. DMacks (talk) 02:01, 22 November 2013 (UTC)

A good source for MSDS is probably in many cases (where it exists) the corresponding article in de.wikipedia. Some of the templates used there to link to the MSDS (de:Kategorie:Vorlage:Datenbanklink Chemie) also exists here (e.g. Template:GESTIS). --Leyo 08:10, 22 November 2013 (UTC)

Is anyone able to create a list of the articles in question of which a de-WP article exists? Or maybe even to restrict the list to articles where the de-WP article has {{GESTIS}} transcluded? --Leyo 13:30, 12 December 2013 (UTC)

Wikipedia talk:Articles for creation/DTTO (Chemical)

Hello, I'm from WP:AfC with a quickie couple of questions. The first is, should this article be listed under the title it's at now or at Ditetrazinetetroxide? Appropriate redirects would be created. The second is, is this a fringe thing? Googling it turns up discussion on forums and a freemade site that is heavily referenced in the article, but the papers I found seem to be lacking - only one seems substantial. I'm unfamiliar with chemicals and chemistry a la Wikipedia in general so I figured I'd ask before I made an ass of myself. --TKK! bark with me! 23:58, 17 December 2013 (UTC)

Looking at the article and its references, I don't think this should be moved into article space. I haven't looked to see if there are sources in the scientific literature, but as it stands the article definitely does not have sufficient backing from reliable sources. Consequently, I have declined the submission. -- Ed (Edgar181) 13:11, 18 December 2013 (UTC)

Perchloromethyl mercaptan

Perchloromethyl mercaptan is showing "Boiling point [Convert: Invalid number]" in the infobox because the infobox contains "BoilingPtC = 147-148", which pases "147-148" as the input number for the conversion. Is there some way to fix this? Johnuniq (talk) 09:10, 18 December 2013 (UTC)

@DePiep: could this be related to the changes you have been making? EdChem (talk) 09:14, 18 December 2013 (UTC)

Fixed it. Thx for the tip. Input now as it should be:

|   BoilingPtC = 147
|   BoilingPtCH = 148

- Could have been in error before we switched to {{convert}} formats this week; don't know how it showed back then. Usage of _CH, |BoilingPtCH=, to show a range of temps is not new in the chembox.

- I only just saved the documentation update Template:Chembox Properties/doc this minute.

- That superscript tag link is added by {{convert}} since one week, to detect bad input. Such pages are nicely listed in maintenance Category:Convert invalid options.

Changes discussed above in #Temperatures_in_Chembox. -DePiep (talk) 09:32, 18 December 2013 (UTC)

From curiosity, I looked at a Google cache of Perchloromethyl mercaptan and it apparently used to say:

Boiling point 147-148 °C, 272 K, -87 °F

It now says:

Boiling point 147 to 148 °C; 297 to 298 °F; 420 to 421 K

I wonder if the infobox really did have the first line above. Johnuniq (talk) 01:25, 19 December 2013 (UTC)

OK, I take the bait. Previous input was: |BoilingPtC= 147-148 (That is _C where single number expected). First, basic trigger |BoilingPt= was empty, so no Boiling value (-tablerow) was shown at all as Juniq noted. Were it triggered, the text shown would be as Juniq says: "Boiling point 147-148 °C, 272 K, -87 °F". That is, C passes the plaintext, F and K calculated from "-1 °C").

Same conclusions: not a {convert} error at all (just bad input for convert), and it came to light because of the template changes intended to calculate the temperatures where possible. Maybe a dozen others popped up this way (in the convert track categories). I've tracked the template elsewhere too for anomalies. -DePiep (talk) 07:58, 19 December 2013 (UTC)

Temperatures in Chembox

 It's live now. Testcases and demos are not current any more. -DePiep (talk) 15:11, 26 December 2013 (UTC) | Melting point |

|-

Ethanol (old)

Identifiers
Properties
Melting point	−114 °C (−173 °F; 159 K)
Boiling point	78.37 °C (173.07 °F; 351.52 K)
Acidity (pKa)	15.9
Hazards
Flash point	9 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ethanol (new)

Identifiers
Properties
Melting point	−114 °C (−173 °F; 159 K)
Boiling point	78.37 °C (173.07 °F; 351.52 K)
Acidity (pKa)	15.9
Hazards
Flash point	9 °C 9 °C (48 °F; 282 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

{{Chembox}} uses temperature calculations in Melting point and Boiling point. I have prepared a proposal (demo) to improve their presentation. Changes:

• Use {{convert}} calculations & formatting. See below for background.
• For negative: use − sign (−) not the keyboard hyphen for output (is still OK for input).
• Use same rounding in all three values (same number of decimals). Follows input.
• In a temperature range, use "to" not "–" (–) to prevent visual confusion.
• Separator is ";" not ",".
• Do not add an extra row in the infobox (whitespace).

Background. Old style presentation flaws are addressed.

{{Convert}} just yesterday switched to module (Lua) code, with very nice and consistent options. Most changes are factual corrections I guess.

The range indicator is "to", not a dash. Because any dash/hyphen would confuse with negative values. This will be applied for all values (also when no negative is in play).

Separator ";". Semicolon is the default for {convert}, so this is used wiki-wide (enwiki). And a comma is used too as a thousands-indicator like in 10,070.45. (Also, changing it to comma would require much more complicated calculations; if possible at all).

Rounding precision (number of decimals) is set by the input. (Old style: the two calculated values are rounded to 0 decimals). More testcases are here.

Check: you can check your favorite substance by previewing this demo. In the article, add the /sandbox and do preview not save:

{{Chembox
...
| Section2 = {{Chembox Properties/sandbox <!-- use /sandbox to test -->
|  MeltingPtC = −114}}
...
}}

Any comments? User DMacks asked me to look at this. -DePiep (talk) 09:10, 12 December 2013 (UTC)

I would suggest that you propose new code for {{Chembox BoilingPt}} and {{Chembox MeltingPt}} (e.g. by making the /Sandboxes for it). Those are the ones that control the data. Someone can than just copy them over. Note, that in the current chembox, editors have a choice between supplying the temperature in C, K or F. --Dirk Beetstra ^{T C} 12:36, 12 December 2013 (UTC)

Good idea! How did I not think of that!?!?! BTW, where do you think the demo's come from? Why "somebody" else? And, more to the point: why don't you write what you think of the proposal? -DePiep (talk) 13:09, 12 December 2013 (UTC)

(-:. Sorry, that was not clear from the original that that was what you did. What I think of the proposal? I think that should be clear from 'Someone can than just copy them over.' :-) .. --Dirk Beetstra ^{T C} 13:18, 12 December 2013 (UTC)

I just want to hear from WPCHEM editors the chem opinion. That is why I came to WT:CHEMS. -DePiep (talk) 14:54, 12 December 2013 (UTC)

Beetstra. As you have read, I was pissed of by your earlier contribution. I'd like all WPCHEM editors, including you, to take a good look at the proposal & make comments as deemed helpful. That could also be questions about code. I suggest you take a good deep look at the testcases suite I mentioned & linked to. In general, I'd expect chem editors to pop up ideas like: "couldn't we do this for selfinflamation temps too?". Or "Why not change the sequence into C-F-K?" There is enough to explore in this. -DePiep (talk) 15:23, 12 December 2013 (UTC)

@DePiep:, I was simply agreeing with this change of using the Lua - the current solution was .. unsatisfactory (though it worked).

In principle, this could be applied to all data (pressure is an obvious one (kPa, Atm, psi?), maybe even weights (lb vs. kg.)/volumes, I am basically indifferent about it - part of WP:BOLD (prepare for implementation / ask for an edit request if it involves protected template) - if there are major issues or objections, someone will revert .. you've got my blessing. --Dirk Beetstra ^{T C} 07:27, 15 December 2013 (UTC)

All fine then. Your general line is clear & helpful. A bold do-and-they'll-reverse still would involve 7 interacting templates to change, or leave unnoticed errors on pages. Me better do a tough test, and ask here before. Also, I'm loyally available to revert myself when trouble would appear. -DePiep (talk) 09:25, 15 December 2013 (UTC)

• Changes for discussion:

Flash point, Autoignition temp now calculated too into C, F C, F, K.

Sequence: C-F-K changed from C-K-F; I'd say the scientific one not in the middle.- DePiep (talk) 16:16, 13 December 2013 (UTC)

I would say, all temperatures into all three (having Kelvins available at a glance makes sense for those who perform thermochemistry). Order is a difficult one - some countries are F-oriented, others are C-oriented. C is the more IUPAC-official, F is commonly used in a lot of countries, and K is for 'chemistry geeks' .. I think that was the reasons that the order was C-F-K (but I don't know for sure why that order was implemented and whether it was discussed). --Dirk Beetstra ^{T C} 07:27, 15 December 2013 (UTC)

All temps in all three four temps, done (flashpoint and autoignite will accept C-F-K values, but now work through a textual "value" only. I'll edit the pages for this effect).

Sequence: C-F-K then for all four, all pages. (No per-article option). Reminder: currently it is C-K-F which I personally find bad. -DePiep (talk) 09:25, 15 December 2013 (UTC)

Should the number of significant figures or decimal places be conserved? EdChem (talk) 08:11, 15 December 2013 (UTC)

Yes, they should be preserved, not rounded by the software. If I recall correctly, the boiling point of water is known up to 4 decimals. IMHO, it should reflect the precision of the measurement, not enforced down (or up!) by us. --Dirk Beetstra ^{T C} 08:19, 15 December 2013 (UTC)

I meant, which? 78.37 °C (173.07 °F; 351.52 K) conserves decimal places but increases significant figures, for example. EdChem (talk) 08:22, 15 December 2013 (UTC)

Yes, rounding is not by same sigfig but by same number of decimals (the {{convert}} default). Since order of magnitude is alike for C-F-K's, this is of invisible or minor effect. EdChem, do you want it researched? Will have to look for the options. Since today's demo already is more correct -in general- than the current round-to-integer calculations, the sigfigs should not be a blocking reason. -DePiep (talk) 09:25, 15 December 2013 (UTC)

I see it is set to same number of decimals. In general, my scientific instinct is that significant figures are what is typically conserved - for example, a synthesis which read 1.234 g (0.012 mol) would, in my view, be incorrect as the chemical amount should be given to four significant figures. However, with a straight unit conversion, I can see the argument for a same decimals approach. It would be dangerous with some conversions, like {{convert|12.345|Pa|mmHg}} produces 12.345 pascals (0.09260 mmHg) but conserving decimals would give 12.345 Pa (0.093 mmHg). Oddly, {{convert|12.345|kPa|mmHg}} produces 12.345 kilopascals (92.60 mmHg), which does not conserve decimals or significant figures. In any event, these sorts of problems seem unlikely to arise with typical temperatures. I am not asking for a change, just raising as an issue for consideration as to whether decimal places or significant figures should be conserved. EdChem (talk) 10:44, 15 December 2013 (UTC)

The Pascal peculiarities we might address when pressures format changes (todo). In most cases we could have options to force a setting per article (say chembox has parameter |BoilingPtSigfig=3 set on an article page). Convert inconsistencies, as your example shows, may need a different approach (or acceptance). I understand both are not present in the temperatures here.

I just found this: {convert|90|C|F K}} → 90 °C (194 °F; 363 K). Making that 190 deg F and 360 K for sigfig reason would look weird to me.

I'll leave it at "same number of decimals", as the demo's do. No sigfig option for temperatures. -DePiep (talk) 11:27, 15 December 2013 (UTC)

Other temperatures?

So I found four temperatures to handle. No more? And any special chemicals to check? Other units like pressure can be dealt with in a next round. -DePiep (talk) 09:25, 15 December 2013 (UTC)

• It's live now. Drop a message when something is awfully wrong.

See also Category:Chemboxes with conversion issues for trackings. -DePiep (talk) 18:03, 16 December 2013 (UTC)

• Will add an option to add a reference. Cannot have that in the same input as the temp value. -DePiep (talk) 04:13, 17 December 2013 (UTC)

I thought there was - 'BoilingPt_Comment' and 'MetlingPt_Comment'. --Dirk Beetstra ^{T C} 06:44, 17 December 2013 (UTC)

Yes, it's called |Melting_notes=. But that one adds brackets and adds a space after the "K", so it shows "K (^[1])". Mostly used to add like "...K (closed cup)", ok. I did not alter that behaviour. When I have a |Melting_ref= added, we can build a sequence "... K^[1] (closed cup)" correctly. We could also move the brackets to the input, giving editor control. Will have to look at current usage for that. Typing all in one parameter requires some switch to manage the space for ref/noref, like: editor must add "_"-trick. I don't think that would work well.

Same for |Boiling_notes=, and I will make parallels with FlashPt and Autoignition (they need the range option too, I saw). -DePiep (talk) 17:16, 17 December 2013 (UTC)

• Text in footer to change into "standard state (at 25 °C (77 °F), 100 kPa)", as per request here. Change will appear together with other changes. -DePiep (talk) 23:25, 17 December 2013 (UTC)

CheMoBot and this data

Related question - how does the data we have here now in these fields relate to what is stored on WikiData? The data there can have references, and I was considering at some point, when I have time (which I do not have; I haven't even considered yet how to do it) to have CheMoBot compare infobox-data with WikiData-data, and 'tag' accordingly (if it is the same (and referenced there), we consider it 'correct'; when they are dissimilar (and referenced there) we consider it 'changed' and then either we or they are wrong, or it has been vandalised (on either side); otherwise we mark it as 'questionable'). That would take away the need to have our indices, and CheMoBot could then easier be used on other infoboxes containing that type of data as well. --Dirk Beetstra ^{T C} 06:44, 17 December 2013 (UTC)

I was having exactly the same idea with {{infobox element}} (for ~126 elements). All the links to the same datapage or source. I talked with wikidata people, but I understood it is long term before we could actually get something from wikidata into an infobox ;-). I can serve some talk links if you want. A bit off-topic it is, because this thread only changes presentation of data, not their value, sourcing or validation. -DePiep (talk) 16:56, 17 December 2013 (UTC)

Not too off-topic - I asked this to know whether the way of storage in our ChemBoxes is 'compatible' with the data in WikiData, that is my main concern at this point. --Dirk Beetstra ^{T C} 12:22, 18 December 2013 (UTC)

In general I'd say that the more specific the parameter, the better the wikidata point. An "any plaintext goes" parameter (like |MeltingPt=) is semantically less clear than a |MeltingPtC= value. But that's as far as I can think. -DePiep (talk) 14:02, 24 December 2013 (UTC)