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Uniformity of Chemical Graphics

When trying to learn about a new chemical I find that contrasting a graphical representation of the chemical in question with one another one really aids my understanding, however a lot of chemicals are illustrated in different styles, making this visual comparison difficult. It would be good to standardize the graphics that appear on the top right. For example I wanted to see the difference between Fructose and Glucose, so I opened two browser tabs for comparison and flicking between them it was hard to see the exact difference between the chemical structures, because the graphic styles were so different. Is there a way we could take a vote on the graphics formats and positions so that this is made easier? If all the articles have the graphics in similar styles and position then people will understand them better. If we can agree on the illustration style then we would have to diligently enforce consistency. First prize would be a way to generate the graphics from the Systematic Name specified in IUPAC Nomenclature. I realize that generating graphics for chemical classes like Ester would be hard since there are unspecified functional placeholder chemicals, but it should be possible. If this is already a discussion somewhere please add that link here. Profhof (talk) 17:40, 11 May 2013 (UTC)

Structure drawing recommendations are presented in our manual of style, Wikipedia:Manual of Style/Chemistry/Structure drawing. Consistent settings would be desirable but is not even achieved in top journals much less in Wikipedia. "Enforcing" drawing styles is not feasible since the graphics files are not editable. Perhaps you will decide to join several of us editors who regularly take on drawing and re-drawing tasks. --Smokefoot (talk) 19:38, 11 May 2013 (UTC)

Is there a guideline on what kind should be used to illustrate infoboxes, in particular? I notice that in the glucose & fructose example there is one pair of comparable drawings, despite the differing choices made for the others (additional drawings preceding versus a solid rendering following).—Odysseus1479 (talk) 02:03, 12 May 2013 (UTC)

OK, great, thanks for the reference link. What software do you prefer or which software do you think is currently the most widely used? Do you think we could achieve the lesser goal of just mentioning the preference of one particular brand of software on the Wikipedia:Manual_of_Style/Chemistry/Structure_drawing page or is this the sort of thing that will start a fight? Is this even a real problem or is it just me? It's not consistency for it's own sake that I'm worried about, it's really about comparing similar structures easily. Do you think there's any real chance of this going into the Wikipedia:Village_pump_(idea_lab) where a collaborative software effort could solve this problem without any hand editing or should I just get better at chemistry? Profhof (talk) 09:53, 13 May 2013 (UTC)

A major factor in this is Wikipedia’s great diversity - we're open to everyone, everywhere and have been running for some time. This inevitably means that virtually every version of every chemical drawing package has been used at some point. Factor in that all images are pooled via Wikimedia - so we're also using images produced by the various foreign language versions of wikiproject-chem - and you're left with a bit of a mess. However, another factor is that new editors often don't read all of the rules before they start editing and frankly, I think the fault for that lies with us. Our current manual of style is 13 pages long (more if you’re including wikiproject-chemicals) and none of these pages are short or make for light reading; they're also not prominently displayed.

I think that one idea for the future might be to have some sort of template ‘welcome’ message. When we notice a new editor making a number of edits to chemistry pages the message can be posted in their talk page. It can contain directions to here as well as project-chemicals and importantly a link to a basic guidelines page. That should be short and deal with the core stuff (schemes in ACS format, please don’t cite web-elements as a source, etc). The rest they can figure out as they go on, like most of us did, but it might head-off common problem with new editors. Random graphics being the least of it. Project Osprey (talk) 10:54, 13 May 2013 (UTC)

I agree, include in 'core stuff' a list of allowed sources for Chembox substance names (PIN, IUPACName, SystematicName, and OtherNames). I am very interested to see what that list includes, because I cannot for the life of me figure that out, even after enquiring from the Project itself. Plasmic Physics (talk) 11:01, 13 May 2013 (UTC)

A clearer intro would probably help, but humans in general don't really like to read documentation. I wonder if it might be better not to rely on the human factor and have a way of generating the graphics in software or at least have an easy way for someone to come in and do so after the fact. Does anyone have any idea of how hard this would be? Profhof (talk) 06:50, 14 May 2013 (UTC)

Do you mean some sort of software embedded into Wikipedia itself, which could automatically generate structures for pages? — Preceding unsigned comment added by Project Osprey (talk • contribs) 09:50, 14 May 2013 (UTC)

Any program can be used, and any program should be allowed. Mandating a single program is against the ideals of the project. Even "professional" publishers do not limit authors in regards to their choice of chemical editing program. Wikipedia:Manual_of_Style/Chemistry/Structure_drawing recommends ACS settings, which all modern programs can replicate.

Jmol may be able to display structures in a 3D manner, simply using the SMILES. It is already implemented in the Chemboxes (click the Jmol-3D images link, e.g. [1]. The project as a whole is more hesitant about implementing it, itself.

While I sympathise with your problem of trying to compare structures on two different pages, the important thing to remember is that each page is standalone in every way. Even varieties of English are allowed to differ between them. --Rifleman 82 (talk) 14:32, 14 May 2013 (UTC)

OK, thanks. I see this might be a lot of work. I do think however that this is one encyclopedia and it would be really good to have one standard. I do also agree that wikipedia's strength is openness and forcing people to do things in a specific way is not democratic. I might still try to think of a way of solving this. Thanks everyone for your input. Profhof (talk) 06:44, 15 May 2013 (UTC)

Coming back to your original problem, would aldohexose or pentose help? --Rifleman 82 (talk) 13:58, 15 May 2013 (UTC)

Plasma

Isn't it time that we remove plasma from the list of 'fundamental states of matter'? It is certainly not a distinct phase from solids, liquids, and gases. There are examples of solid plasmas termed 'dusty/grainy plasmas', there are liquid plasmas such as 'ionic liquids'. We're all familiar with the regular 'gaseous plasma'. It's even possible to create a 'supercritical plasma.' Plasmic Physics (talk) 00:17, 15 May 2013 (UTC)

AfC submission

Just a heads-up about this submission at AfC. Regards, FoCuSandLeArN (talk) 20:43, 19 May 2013 (UTC)

User:Andy Dingley

It seems like we have another problem editor. I encountered him while editting silicon related articles and categories. Recently he created a new category. Following the category style recomendations, I removed excess material from the top of the category that should go in an article, as it does not contribute to the clarification the subject of the category. I was immediately reverted without explanation. I reverted only twice thereafter, with the above reason given and an invitation to discuss. I also gave him goodfaith warning of the 3RR. Then I received the 3RR warning proper in return, posted on my talkpage.

I've also had troublesome encounters with him concerning the categorisation of other silicic articles, this user seems to be engaged in an uncooperative and passive POV style of editting. It would be nice if someone could keep an eye on him. Here is the history of the relevant category: [2]. Plasmic Physics (talk) 12:40, 23 May 2013 (UTC)

You object to your empty category Category:Silicon mixtures having the alloy content sub-catted to Silicon alloys. You have edit-warred since because (as seems to be a historical feature of your editing), it's "your way or the highway".

I'd also note that when forumshopping to bitch about other editors, it's considered polite, and a formal requirement across the WP:ALLCAPS world, to also notify the other editor. Andy Dingley (talk) 12:46, 23 May 2013 (UTC)

Note: 'complaining' is different from 'notifying', and this is not a formal process in any case, so your notification is not requisite. Plasmic Physics (talk) 13:04, 23 May 2013 (UTC)

A development: there is now a discussion with Andy taking place on my talkpage. Plasmic Physics (talk) 13:42, 23 May 2013 (UTC)

article title: 2-Pyridone or 2-pyridone

There is a requested move on the 2-Pyridone page. There are countless examples of 1-Methyl... or 2-Phenyl.... articles in wikipedia. Should all be moved to 1-methyl... or 2-phenyl....? --Stone (talk) 16:48, 26 May 2013 (UTC)

Fortunately our MOS covers this. For page titles the first letter is capitalised, as it would be at the start of a sentence. Frankly though, its not a major problem, as the search function isn't case sensitive. Project Osprey (talk) 18:51, 26 May 2013 (UTC)

Thanks.--Stone (talk) 20:41, 26 May 2013 (UTC)

Szilard–Chalmers effect

I wonder if this new article should be merged somewhere... FoCuSandLeArN (talk) 03:03, 28 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) 15:47, 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)

Charge transfer band vs Charge transfer complex

At Talk:Charge-transfer complex#Most of this article seems to be off-topic, a discussion is going on about the splitting of [transfer band] from charge transfer complex. Specifically the now reverted CT band article was to about optical transitions and the CT complex article was to be about salts. These topics are discussed pretty separately often, at least in the classroom, probably because CT bands are seen more commonly in compounds that would not be classified as CT salts, say [Ru(bipy)₃]²⁺ etc. Advice is welcome if you have some understanding of these phenomena.--Smokefoot (talk) 01:54, 3 June 2013 (UTC)

Catalytic oxidation

Comments are also welcome at Talk:Catalytic oxidation with regards to how we should handle this very large topic that seems to have been slightly neglected. --Smokefoot (talk) 13:43, 3 June 2013 (UTC)

Arsenic trioxide

Everyone learns that a chemical compound with no numerical prefix attached to the first element represents one atom. But arsenic trioxide has two arsenic atoms; yet it has a name that implies it has one (that is, its name implies AsO3, not As2O3, which would be diarsenic trioxide.) Any thoughts?? Georgia guy (talk) 17:17, 8 June 2013 (UTC)

Not necessarily. However, I think that the article should be renamed to remove the ambiguity. Plasmic Physics (talk) 22:47, 8 June 2013 (UTC)

Well then, just propose a move at WP:RM. Georgia guy (talk) 22:55, 8 June 2013 (UTC)

First of all, the statement "Everyone learns that a chemical compound with no numerical prefix attached to the first element represents one atom" is untrue. I did not learn that and my experience is that such a guideline would be pretty pretty misleading. Second, my experience is that most people call As₂O₃ arsenic trioxide. Although your comments are very welcome and certainly well motivated, we need to remember that Wikipedia exists (IMHO) to help people seeking information, not to enforce perceptions of nomenclature rules. --Smokefoot (talk) 23:21, 8 June 2013 (UTC)

It's not about enforcing perceptions of nomenclature rules. It is to clear up ambiguity, arsenic trioxide could be a double oxide, like lead trioxide, or anything else. You don't know until you read the article. Plasmic Physics (talk) 23:35, 8 June 2013 (UTC)

What is a double oxide?? Is water an example?? Georgia guy (talk) 23:30, 8 June 2013 (UTC)

A double oxide, is where the non-oxygen component exist in a mixed formal oxidation state. Lead tetroxide is actually lead(II,IV) tetroxide.

(edit conflict) To leave it as it is, would require the reader to be esoterically familiar. Plasmic Physics (talk) 23:33, 8 June 2013 (UTC)

My impression was that names like "diarsenic trioxide" were never used unless there was a known compound AsO₃ (which there isn't!). Similar things occur with "phosphorus pentoxide" (a name I personally hate, since it's P4O10, but everyone calls it phosphorus pentoxide anyway), as well as phosphorus trioxide, antimony trioxide, etc.. As₂O₃ is generally called either arsenic trioxide or arsenic(III) oxide, so we should make one of those names the default. A quick look at common usage:

• Alfa and Aldrich use arsenic(III) oxide as the main name, with arsenic trioxide as the second name (Aldrich recognises diarsenic trioxide as a third name, but only for one specific grade!). Fisher uses only arsenic(III) oxide. I know in catalogues they like the Stock name as it means that similar things are listed together.
• A search in the ACS database gave 889 hits for arsenic trioxide, 28 for arsenic(III) oxide, but only 5 for diarsenic trioxide.
• A search in the RSC database gave 367 hits for arsenic trioxide, 21 for arsenic(III) oxide, but only 8 for diarsenic trioxide.

If those numbers were closer there might be a case to make, but I think this is pretty clear, we need to keep the name the same. Walkerma (talk) 00:13, 9 June 2013 (UTC)

According to the Project, using databases as a source of nomenclature, is not an acceptable practice. Plasmic Physics (talk) 00:31, 9 June 2013 (UTC)

Moreover, my concern made at 23:33 still remains unresolved by your reply. Plasmic Physics (talk) 00:34, 9 June 2013 (UTC)

As(I,III) trioxide can also be called arsenic trioxide, since it has the formula As
₄O
₃. Plasmic Physics (talk) 00:44, 9 June 2013 (UTC)

(edit conflict) AsO₃ is impossible unless there are O-O bonds, As₂O₃ is the "expected" formula based on the periodic table, As₃O₃ and As₄O₃ are perhaps theoretically possible as mixed valency oxides, though they would have to involve either As(I) or As-As bonds. Given that those are unknown or rare, it's not surprising that chemists consider arsenic trioxide to be clear enough to be the common name.

BTW, I just created a redirect for diarsenic trioxide, and I think that should address Georgia guy's concern, though I think the fact that the article's been around since at least 2005 without that redirect suggests that it's not commonly used. There is already a redirect for As2O3. Does that address your concern as well? Walkerma (talk) 01:03, 9 June 2013 (UTC)

I'll just say "yes", purely because I'm tired of this discussion, and it's more troublesome than it's worth. Though you said yourself that "...it's not surprising that chemists consider...", which just reinforces my concern. Plasmic Physics (talk) 01:33, 9 June 2013 (UTC)

Fun, isn't it. Look, Plasmic Physics, nomenclature is always a difficult topic (XTC, MDMA, LSD, tetraphosphorus, octasulfur .. do people always get to the technical correct name when they type the common name?). Yes, we don't allow databases as our references, and most naming, even as implied or instructed by IUPAC, is still ambiguous, or incomplete (following the rules to strict does sometimes result in wrong names). Naming of compounds is not a form of algebra. Our naming conventions are pretty clear, we use names that are the ones most commonly used, making the other ones redirects (possibly all). So acetic acid in stead of ethanoic acid. arsenic trioxide in stead of diarsenic trioxide. And as Odysseus already mentioned, nitric oxide and nitrous oxide are other ones. Those are the names used by the people and how they know stuff, the rest redirects there. After typing either of the names, they should go to the correct article, and the lede should then clearly explain what the compound is, in language clear for non-chemists, so that the occasional non-chemist who sees in popular science or in the news 'arsenic trioxide' pop up, can find the article and understands what it is. Don't you think that it is equally confusing when the general talk is about 'arsenic trioxide' and people going to Wikipedia are directed to 'diarsenic trioxide' - they might well think "but the article I saw on CNN said 'arsenic trioxide', this is not the same". We don't expect the reader to be, as you put it, esoterically familiar, we expect the reader to get to the article and be able to read the explanations. And that's why we are here, to serve the reader, who should be directed, preferably, to the article using the most commonly used name, even if that name is, technically, incorrect. We are writing an encyclopeda here, and we have the freedom to follow our rules in that. As a side note, if you want your restrictions to be lifted, Plasmic Physics, for me (at the least) 2 things would be: first drop complaining and making remarks about how your colleagues in this wikiproject are treating naming conventions, and secondly to stop to adhere so strictly to said naming conventions, there's no chemist who adheres to them that strong anyway. So indeed, Wikipedia is not about enforcing perceptions of nomenclature rules.

If there is another, very uncommon compound which would also correctly be named 'arsenic trioxide', then that would probably be needed to be named differently (maybe also at a technically incorrect name), and the lede of (the common) Arsenic trioxide could then point to the uncommon variety. Otherwise a disambiguation-type page would be needed. For now, most people know this compound, As2O3, as 'arsenic trioxide', so that should be the place of the article, and redirects should be in place for the rest. I hope this explains. --Dirk Beetstra ^{T C} 05:39, 9 June 2013 (UTC) (adapted --Dirk Beetstra ^{T C} 05:41, 9 June 2013 (UTC))

Beetstra is correct that nomenclature decisions need to be based on helping the reader. We have phosphorous pentoxide despite its actual molecular composition being P₄O₁₀. We have nitrogen(IV) oxide pointing to NO₂ despite the fact that N₂O₄ is an equally plausible target based purely on nomenclature rules. There is a redirect from diarsenic trioxide to the (common-even-if-inaccurately-named) arsenic trioxide and with no other plausible compound suggested for either name, we are left with arguing whether to have the article at A with a redirect from B or at B with a redirect from A. Anyone believing the article should be moved can start a request to move it at the relevant article talk page, and when it is shot down in flames for the reasons outlined above, we can all move on. Alternatively (and preferably), as this thread has ensured the appropriate redirects exist and achieved a broad consensus, we could move on without a doomed RM discussion. EdChem (talk) 07:13, 9 June 2013 (UTC)

(edit conflict) I've already folded, and am no longer arguing the matter. This seems to me like a case of beating the dead horse. If you insist, I'll respond in any case.

The IUPAC nomenclature system is an a way algebraic, since, by selecting a particular algorithm from an allowed set, generates a set of solutions that relates to the chosen variables. It falls under set theory, which requires algebra. The general person would not be confused if it was mentioned in the lede of a 'diarsenic trioxide', that the di- prefix is commonly omitted. I believe that there is a WP guideline that permits the ignoring of WP policy under special conditions - it is not always appropriate to use the most common name. I normally support the common name for the article title over the IUPAC name, but not at the cost of being correct. Although, as I said, it does not matter what is done.

The only reason why I am complaining and making remarks about how others in this Project are treating naming conventions, is because no one is taking the issue seriously. If users in general, are to stop adhering to IUPAC nomenclature for filling the corresponding infobox fields, why have them? Moreover, why am I expected to take everyone else at their word, when they say something is named such, but the courtesy is not returned? I'm expected to cite every name I add, and it is conspired against me to make it very much impossible, reminiscent of the lyrics of Scarborough Fair by Simon & Garfunkel. Plasmic Physics (talk) 07:53, 9 June 2013 (UTC)

My recollections will be somewhat dated, but it was usual practice to omit prefixes from the first element; where disambiguation was necessary suffixes were preferred, as in nitric oxide and nitrous oxide (but dinitrogen tetroxide). I believe IUPAC still calls for the Roman numerals indicating oxidation state: would it help clarify matters if the name arsenic (III) oxide appeared in the lead? I would also like to point out that WP articles should be given the subject’s most usual name in RSs, not necessarily the most logical or descriptive. (The latter are well enough served by redirects.)—Odysseus1479 03:29, 9 June 2013 (UTC)

I believe the means for resolving this already exists within the Chembox code. There are options for IUPACName, SystematicName, OtherNames and what may be considered general name (which would be the name that appears at the top of the box). I have edited the page to try and resolve this dispute to the satisfaction of all parties... Also, I've included a key for the structure, which is something I think we should all start doing.Project Osprey (talk) 10:53, 9 June 2013 (UTC)

Environmental Chemistry

I will be overhauling the Environmental Chemistry page over the next week or two, adding a good amount of what I hope will be high quality new material. I would love any and all input and/or suggestions... Aside from editing random sentences here and there on various pages this will be my first major input to an article. For reference and so everyone knows, I am a senior majoring in chemistry with an environmental concentration, at Texas A&M University Corpus Christi. No graduate degree obviously, but I am determined to make additions which will be welcomed by the wikiproject chemistry.

In the next few days I will prepare a list of major changes I intend to make and post it on the talk page for discussion. In the mean time, I've edited the intro quite a bit so far, which I consider as 'under construction.' EzPz (talk) 17:15, 11 June 2013 (UTC)

puzzle

sodium diacetate
sodium sesquicarbonate
acid salt — Preceding unsigned comment added by 67.171.99.229 (talk) 18:26, 11 June 2013 (UTC)

Acid salt is a real thing, it's sometimes also called a 'half salt'. Say you have a molecule with two acidic groups (e.g. Malonic acid) and you neutralise one of them; what you're left with is part salt, part acid - hence an acid salt. The other two I do not like, they appear to just be a 1:1 mixtures that have been given special names. Project Osprey (talk) 19:05, 11 June 2013 (UTC)

Edit-a-thon Invitation

Please join the Chemical Heritage Foundation Edit-a-Thon, June 20, 2013. Build content relating to women in science, chemistry and the history of science. Use the hashtag #GlamCHF and write your favorite scientist or chemist into Wikipedian history!

We would love to have you join us in the Edit-a-Thon next week (remotely or in person). Mary Mark Ockerbloom (talk) 20:18, 13 June 2013 (UTC)

Homologous series vs. oligomeric series

Is there any clear definition on what a homologous series and an oligomeric series are? If we consider e.g. cyclic alkanes, cyclic dimethylsiloxanes or crown ethers of different ring sizes, what would be the more appropriate term? Thank you in advance, 129.132.225.23 (talk) 12:54, 21 June 2013 (UTC)

In my world, the contrast is made between oligomers and polymers, which describe families of compounds with very similar formulas. IUPAC offers a nice definition of an oligomer here http://goldbook.iupac.org/O04286.html. Unlike the case for a polymers, the removal of a monomer unit from an oligomer changes the properties of the material. A homologous series is different. The term describes several materials or compounds that are related in some manner.--Smokefoot (talk) 13:43, 21 June 2013 (UTC)

It seems to me that according to your statement, several examples under Homologous series#Examples are in fact oligomeric series, not homologous series. Or did I misinterpret your statement? If so would you mind giving a few examples for an oligomeric series? 129.132.225.23 (talk) 14:10, 21 June 2013 (UTC)

These concepts are completely distinct. A compound can be an oligomer. A series consists of several compounds. Several oligomers can form a homologous series. Probably we could move this conversation to Talk:Homologous series.--Smokefoot (talk) 14:16, 21 June 2013 (UTC)

For a series of e.g. hexachlorocyclopropane, octachlorocyclobutane, decachlorocyclopentane, dodecachlorocyclohexane, etc. which is the more appropriate term? This is still unclear to me. BTW: Google gives much less hits for "oligomeric series" compared to "homologous series". 129.132.225.23 (talk) 14:59, 21 June 2013 (UTC)

Hydrogen split

I think that it is a good idea to split Hydrogen into Hydrogen and Hydrogen (chemical). Any second opinions? Plasmic Physics (talk) 12:22, 19 June 2013 (UTC)

This gives the reader the ability to investigate hydrogen as an element, or alternatively, to investigate the chemistry of diatomic hydrogen specifically. It also frees up space/opportunity for more speciallised information on dihydrogen as a chemical. Plasmic Physics (talk) 12:33, 19 June 2013 (UTC)

Hydrogen can handle hydrogen as a component of other compounds, hydrogen-bonding, hydrogen physics, etc. While Hydrogen (chemical) can handle hydrogen uses, reactions that consume or produce dihydrogen, and its economic value, etc. Plasmic Physics (talk) 12:44, 19 June 2013 (UTC)

IMHO your editing is so strange, so unhelpful, and often so (unintentionally) mediocre, that my recommendation is that you contract your editing in the Wikipedia Chemistry space. Of course this is only my opinion. --Smokefoot (talk) 13:34, 19 June 2013 (UTC)

Can we please keep on topic? This is not a discussion about me, or my edit history. Plasmic Physics (talk) 13:57, 19 June 2013 (UTC)

Is there any element where we presently have one article on the element, and a different article on the substance? My hunch is that the answer is no, and that there is a good reason that that is the case. EdChem (talk) 14:02, 19 June 2013 (UTC)

We may not have done that for an element, but we have done it for water. So, please do tell - what is this good reason? Plasmic Physics (talk) 14:13, 19 June 2013 (UTC)

Not quite the answer you were looking for, but I do believe that we have both Hydrogen Chloride and Hydrochloric Acid.--Gilderien Chat|List of good deeds 14:17, 19 June 2013 (UTC)

Now that is an interesting situation. I don't actually agree with that split, there is too much overlap in its current form. I doubt that anything more than a splinter will remain if all significant overlap was removed from Hydrochloric acid. It seems as though it was created on a whim, rather than by reason. Plasmic Physics (talk) 14:24, 19 June 2013 (UTC)

• A brief search says no - but I haven't checked every element page. Hydrogen is the most searched for element (see toolserver) getting some 14.7K hits a day. I would expect most of these readers aren't chemists, so I don't think its fair of us to expect them to know if they what to learn about the element or the molecule. An overview of hydrogen-in-general serves our readers best and that is currently what we have. I don't see an advantage in splitting that apart to allow for niche editing opportunities.Project Osprey (talk) 14:56, 19 June 2013 (UTC)

I don't see any reason to split, this article gives a nice overview now, and is not too big. It was even featured in this form in the past. Perfect. --Dirk Beetstra ^{T C} 14:03, 19 June 2013 (UTC)

I just gave a reason. The WP:Splitting article say that as an article of ~75kB, it should probably be spilt, so it meets the size criteria for splitting. However, that is not why I brought it up. Like I said, it is about navigability. The current hydrogen article covers such a broad range, without sufficiently exploring every topic in depth; and not all readers are interested in content that is not related to dihydogen, and will find it difficult to extract relevant information due to its interspersion within the article. Moreover, like fashion, judgment of good standards comes and goes - what it takes to be a quality article yesterday, is not necessarily the same tomorrow. Plasmic Physics (talk) 14:13, 19 June 2013 (UTC)

no reason to split, if the article is too big we can look at duplicate content, some content on hydrogen production can be moved to the hydrogen production article. V8rik (talk) 18:46, 19 June 2013 (UTC)

As I'm saying, it is not about size. Plasmic Physics (talk) 22:27, 19 June 2013 (UTC)

Expanding on my earlier comments:

1. With regard to the water articles, there we have a term with relevance to a myriad of topics separate from the narrow water-as-chemical topic - its importance for living organisms, involvement in weather, cycles in the environment, the need to discuss fresh, salt water, soda and mineral waters, water pollution and associated politics, applications, etc. I do not think water and hydrogen are comparable in this regard.
2. On the separation of hydrogen chloride and hydrochloric acid, that's not a good idea as it is not a natural separation - the notion that concentrated hydrochloric acid is explained in article A but the white smoke evolving from the solution belongs in article B, and then that when that white smoke enters a person's nose and dissolves in mucous membranes it returns to article A is fairly ridiculous.
3. The reason I was alluding to was that the separation is not made for other elements is because it is artificial and somewhat arbitrary, as a start. Project Osprey has commented on the logic from an encyclopedic organisation perspective - some readers are likely to search for hydrogen seeking the element, some the substance, and expecting them to distinguish is unreasonable. At least with water, the main article covers the substance and basic properties as well as other characteristics with a section on properties that links to the related article.
4. Expanding the space just allows coverage of material that really does not belong on a main article on hydrogen. I could write a section on organometallic complexes of dihydrogen, link in the catalytic cycle of Wilkinson's catalyst, then lead into asymmetric hydrogenation and industrial production of L-DOPA. If I did, I would expect to be criticised (and rightly so) because those materials are not appropriate for the hydrogen article beyond a link to a relevant article. Make space and it will be filled. What you need to do is identify material that belongs in the articles and is missing to justify making space for its addition.
5. Unless I am missing something, I don't expect that you will get consensus for a split.

Regards, EdChem (talk) 01:28, 20 June 2013 (UTC)

OPPOSE We do not split general topic articles on WP, just because we can think of ways to do so-- see WP:SS. Water has been mentioned. And we have an article on Earth-- the planet. The article on United States of America is twice as long as the hydrogen article, yet the U.S. does not make up 75% of the known ordinary matter universe (despite some patriotic delusions by a few of its citizens), and yet we do not split this one. It is quite fitting that hydrogen is our longest element article.

We have resisted splitting articles on many elements into articles on the free element vs. everything else. We already have hydrogen atom and I expect there is room for a similar hydrogen molecule (now redirects to hydrogen) if you want to discuss the quantum mechanics of it. There may even be room for an article on hydrogen chemistry (as we have organic chemistry for carbon!), but leaving a summary behind in hydrogen, not splitting it out. We cover a lot of production stuff and use of the element in hydrogen fuel, yet a summary remains behind in hydrogen. In short, I think this a bad idea. Write the subarticles and summarize them in hydrogen. There is no limit to this, as you see in the examples above, from water to fire to Earth to air. So I vote no. SBHarris 02:01, 20 June 2013 (UTC)

In spite of the opposition, I approve of this sort of unbiased discussion. Rather than saying 'no' because I say so, pros and cons are compared. I wish we had more users here with that approach. Plasmic Physics (talk) 02:17, 20 June 2013 (UTC)

The usual experience is getting bigotedly steamrolled. Plasmic Physics (talk) 02:20, 20 June 2013 (UTC)

Plasmic Physics, please do not imply that other editors are bigots or practising bigotry towards you, without substantial evidence and justification. The discussions both here and at talk:Methyl radical may not support your views but that does not make those who disagree with you are steamrolling you and motivated by bigotry. I object to the insinuation of bigotry. EdChem (talk) 04:26, 20 June 2013 (UTC)

I did not say everyone else does this, nor did I name any specific user(s). Plasmic Physics (talk) 04:43, 20 June 2013 (UTC)

True, you just made a general smear that says that bigotry and steamrollering are "usual". EdChem (talk) 04:59, 20 June 2013 (UTC)

Yes, and observation can't be wrong - that being the usual is just what I observe. Don't take it so personally. Plasmic Physics (talk) 05:10, 20 June 2013 (UTC)

no, basically what you say is that any opposition you encounter is based on bigotry. Your bigotry statement is directed at anyone who has ever opposed you. The damage is done and there is no need to name a specific user. If Wikipedia would have any believable procedure in place to ban people I would have banned you for a week. If on the other hand you would quickly apologize we could move on. V8rik (talk) 20:07, 20 June 2013 (UTC)

When did I say that? You're putting words in my mouth. I don't like being misquoted. Plasmic Physics (talk) 22:36, 20 June 2013 (UTC)

There was a very short discussion on the splitting of the oxygen article. Number 33 in the index Talk:Oxygen/Archive_1 Split O2 to its own article.--Stone (talk) 09:23, 20 June 2013 (UTC)

Well, it does actually have its own article(s): Triplet oxygen and Singlet oxygen, which is another example of a bad idea. I would support a single article for Oxygen (chemical), but one for every state is overkill. This pair is within the same group as the Hydrochloric acid and Hydrogen chloride pair stated above. Plasmic Physics (talk) 11:24, 20 June 2013 (UTC)

Still missing my point. Per wp:ss there is no overkill so long as you can come up with enough WP:RS sources to write one. The work is infinitely expandable. We can write singlet oxygen in photosynthesis, if we like. Or singlet oxygen in hot tub sanitation. Whatever you like, as WP is never done. WP:NOTFINISHED. But don't kill or split summary articles to make subarticles. Leave summary articles as summary articles to avoid content forking at the same level of detail. At each level of summation and review, summary peices have their own place, their own function and charm. And their construction and balancing is the very essence of what WP does. Please absorb this. SBHarris 23:07, 20 June 2013 (UTC)

That is not what I meant by overkill, I was referring to EdChem's comment on HCl acid v.s. HCL: "2.On the separation of hydrogen chloride and hydrochloric acid, that's not a good idea as it is not a natural separation - the notion that concentrated hydrochloric acid is explained in article A but the white smoke evolving from the solution belongs in article B, and then that when that white smoke enters a person's nose and dissolves in mucous membranes it returns to article A is fairly ridiculous." Plasmic Physics (talk) 23:18, 20 June 2013 (UTC)

So? If you leave your dynamite sitting around it will soon begin to drip liquid nitroglycerin (separate article). If you manage to collect this and dissolve it again in diatomaceous earth without blowing yourself up, you will get dynamite again, and now you're back to what you call article A. This is not a reason to have just one article (in fact we have three, as there's yet another on the pharmacology of nitroglycerin: glyceryl trinitrate (pharmacology). In cases where a combination of two things has different properties than the things on their own (e.g. aqua regia) that's plenty of reason to split them. Simply having too much information on one or the other (as in the example of the pharmacology of nitroglycerin) is reason enough split them, while leaving a summary behind. And indeed, hydrochloric acid (the HCl+water mix) does contain material on hydrogen chloride, and vice versa, but the focus of each article is different.

In this case, neither one can be said to be the master article, so perfect nested outline form is sometimes not possible on Wikipedia. In other cases, it is. As I said in TALK:alcohol to somebody who wanted to shoehorn in a long section on alcohol and cortisol, that article is long enough to stand alone, and per WP:SS should have been a "main article" for an adrenal or cortisol effects subsection in the already existent Long term effects of alcohol which in turn is a subarticle for alcoholism which in turn is a subarticle for ethanol which is in turn a subarticle for alcohol which (in the case of that article) refered to a general chemical class of R-OH compounds, of which ethanol is (of course) only one. You see the point? SBHarris 00:51, 21 June 2013 (UTC)

There seems to be some sort of misunderstanding, as of my comment at 02:17, 20 June 2013 (UTC), I am no longer pushing for a split. So you're really just arguing an idea that's already dead, into the grave. This new thread is simply a response to Stone's comment. Plasmic Physics (talk) 01:36, 21 June 2013 (UTC)

Sorry! I did not want to start another discussion.--Stone (talk) 09:51, 26 June 2013 (UTC)

There is no need to apologise, it does not seem as though you intended any malignant consequences. All that followed was others' doing, whether for good or bad. Plasmic Physics (talk) 10:57, 26 June 2013 (UTC)

Volatile sulfur compounds ?

Hello,

I was trying to find a destination to wikilink Volatile sulfur compounds and found no ideal target. We have Organosulfur compounds, volatile organic compounds and Volatility (chemistry) ... but as I understand it not all VSC are organic, e.g. H2S, and presumably not all organosulfur compounds are volatile.

Does Wikipedia need a VSC article? If no what article(s) should I link VSC to please?

Thanks,

Lesion (talk) 18:37, 5 July 2013 (UTC)

We do not seem to have such an article, but we do have Volatile organic compound. Guessing that you are interested in the smelly variety, the problem with the topic of "volatile sulfur compounds" is that many have only faint or even sweet odors, so such an article would possibly not satisfy your interests. The best link is Thiol#Odor in my opinion. --Smokefoot (talk) 00:17, 6 July 2013 (UTC)

• Looking through your edit history, I'm guessing this is to do with the Halitosis page. Of the 4 sulphur compound listed there 2 are thioethers and 2 are thiols. Chemically these are fairly similar so I'd go with Smokefoot's recommendation as that page has a better description of their odours.Project Osprey (talk) 07:40, 6 July 2013 (UTC)

• • I see the problem, but the issue is how to classify them as 'volatile sulfur compound'. Due to the strong smell of these compounds, even the ones that we would classify a not being a volatile according to the definitions in Volatile organic compound would probably be volatile enough to smell (Elemental sulfur smells ..). I agree with Smokefoot and Project Osprey, that a link to a section in a general sulfur-compound-article about their smell (like Thiol#Odor, I don't know if Thioether#Odor exists?) would be the best. --Dirk Beetstra ^{T C} 07:50, 6 July 2013 (UTC)

Thanks for advice. Thiol#Odor and Thioether#Odor do seem to be the most relevant pages for this. Yes it was for the halitosis page which I'm currently working on. I have limited understanding of chemistry, so I ask can the 3 main VSC that keep getting mentioned in sources: H2S, CH3SH and CH3SCH3; all be called both thioethers and thiols? Per the thioether page, R-S-R would mean yes, but the lead says that it is C-S-C, which would mean that the first 2 are not thioethers? Conversely, the first 2 could be called thiols, but not sure if dimethylsulfide is a thiol since there is no H directly bonded to the Sulfur? Sorry to be a pain, but still confused. Lesion (talk) 09:53, 6 July 2013 (UTC)

• Not to worry, it's best that these things are written up correctly. allyl methyl sulfide and dimethyl sulfide are thioethers, methyl mercaptan is a thiol. Hydrogen sulfide is, inconveniently, not an organosulfur compound, as it does not contain carbon (sorry to generate confusion here, I was thinking of it as a thiol before but that's not really an accurate description). I sense that you would prefer to have single chemical name to cover all of these compounds, which is a bit of a push, but I suppose sulfides is broadly accurate.

• OK great. How about this =

... [[Volatility (chemistry)|volatile]] [[sulfur]] [[Chemical compound|compounds]] such as [[hydrogen sulfide]], [[methyl mercaptan]], [[dimethyl sulfide]], and [[allyl methyl sulfide]]. All these [[sulfide]]s are classed as [[organosulfur compound]]s apart from hydrogen sulfide, which does not contain carbon.

Organosulfur compound also looks like a parent article for thiols and thioethers etc. Lesion (talk) 11:42, 7 July 2013 (UTC)

Transformed the redirect Irreducible representation into an article

Even just looking at the edit history, and more importantly after a discussion on my talk page, this is a desperately needed article and would help fill gaps in WP on group theory in theoretical physics and chemistry. I thought that at least something of a definition with some links and sources (to be moved inline) is far better than the annoying redirect to simple module, and decided put the draft in mainspace so others with expertise/interests in group theory can see and/or edit it. Needs a lot of work which I'll hopefully get to finish (recently busy...). M∧Ŝc²ħεИ_τlk 21:49, 7 July 2013 (UTC)

ChemWeb

Hello. I have created an article on ChemWeb which now resides on one of my personal sandbox pages. I am wondering if this is considered a notable topic and there is a discussion taking place at WikiProject Academics, here. And so, it was suggested that I also solicit comments from members of this project. I thought this was a good idea. Therefore, your comments and suggestions over at WP Academic Journals would be much appreciated. ---- Steve Quinn (talk) 23:44, 7 July 2013 (UTC)

Wikidata

Hi, I need your feedback about the properties used to describe a chemical in Wikidata: do we need more properties ? If yes, which ones ? Please have a look atWikidata and give me an answer here or there. Thanks Snipre (talk) 07:28, 12 July 2013 (UTC)

GAR

Radon, an article that you or your project may be interested in, has been nominated for an individual good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article.--FutureTrillionaire (talk) 01:18, 17 July 2013 (UTC)

Patchy particles

Dear chemistry experts: There is an article at Afc right now, Wikipedia talk:Articles for creation/Patchy Particle which is difficult to review because the submitter has limited skill at writing in English. It could use some attention from someone who has a clue what patchy particles are, and can copyedit the text without incorporating errors. Am I asking in the right place? —Anne Delong (talk) 09:23, 18 July 2013 (UTC)

What are layered quantum dots called again? Whatever they're called, I think the user is referring to them. Plasmic Physics (talk) 11:43, 18 July 2013 (UTC)

I found what I was looking for: Core–shell semiconductor nanocrystal. Plasmic Physics (talk) 12:35, 18 July 2013 (UTC)

On second thought, although related they are not the same. Anisotropic quantum dots (patchy particles) are not radially differentiated, but are laterally differentiated, meaning they different compositions at at least two points, which are at the same radius. Plasmic Physics (talk) 12:47, 18 July 2013 (UTC)

Variable Hybridization

Do I understand correctly that this 19-hours-old article is an illegitimate content fork of orbital hybridisation? Incnis Mrsi (talk) 16:07, 19 July 2013 (UTC)

• not to me? looks like a specialist topic within the realm of orbital hybridization V8rik (talk) 21:07, 19 July 2013 (UTC)

Chembox

Hi All, I recently did an readout of all chembox properties templates and I found and fixed a lot of wrong written parameters, which prevented the values from being displayed. I also documented some parameters which are implemented but were not documented. I found that the following implemented parameters are only used a single time and could be discontinued to reduce complexity, because they are much to specific:

• CriticalRelativeHumidity
• Bulk Conductivity
• Sheet Resistance
• Methacrylate Equiv Wt
• AveragePoreSize
• PoreVolume
• SpecificSurfaceArea

Instead I suggest we support the following parameters which were used by authors several times assuming they work:

• Young's Modulus
• HeatofSolution
• Heat of Vaporization
• CriticalPt
• SurfaceTension
• Solubility equilibrium

Another thing is that the Parameter: Dipole is used and implemented in both this section and the structur section this should be consolidated. But where? --Saehrimnir (talk) 05:45, 22 July 2013 (UTC)

First, thanks for that hard work, that is a good thing what you did!

Are those first ones implemented? .. many are way too specialised, or 'aspecific'. PoreVolume .. does that not depend on how you prepare a material, or is it for zeolites with a specific preparation. Could you with those list where they are used?

The others are nice, and could easily be implemented. I'll try to find time for that. Proper names for the parameters should be created - without spaces and diacritics etc.

One other question, I noticed you changed odor <-> odour. How many parameters do we have that have possible spelling differences between flavours of English? For those, I would suggest that both are activated as working (I think that does the trick nicely in the appropriate template. --Dirk Beetstra ^{T C} 06:42, 22 July 2013 (UTC)

I'd like to repeat a comment I made on Template_talk:Chembox back in January: Why isn't Gibbs free energy of formation included, when enthalpy of formation is? It's an important number for checking feasibility of reactions and estimating the temperature at which the Gibbs free energy of a reaction changes sign (using ΔH/ΔS which equals 298.15K×ΔH/(ΔH−ΔG), see Ellingham diagram). Eric Kvaalen (talk) 07:27, 22 July 2013 (UTC)

Yes the first once are implemented:

• AveragePoreSize, PoreVolume, SpecificSurfaceArea are use only in Poly(2,6-diphenylphenylene oxide)

*Bulk Conductivity, Sheet Resistance, Methacrylate Equiv Wt are only used in PEDOT-TMA not implemented but documented?!?

• Ammonium sulfate is the single use for CriticalRelativeHumidity.

As for the names for the new parameters I would suggest:

• Chembox properties
  • YoungModulus
  • CriticalPt
  • SurfaceTension
  • pKSolution
• Chembox Thermochemistry
  • DeltaGf
  • SolutionEthalpy
  • VaporizationEnthalpy
  • MeltingEnthalpy

I think the only other spelling difference would be vapor and vapour. In VaporPressure and if implemented in VaporizationEnthalpy. --Saehrimnir (talk) 21:22, 22 July 2013 (UTC)

Periodicvideos

I got a very encouraging response from dr brady of the periodicvideos youtubechannel saying we may be able to use some screenshots if we provide them with sufficient credit. Are there any gaps on here where certain of their videos might illustrate something interesting? --عبد المؤمن (talk) 01:01, 23 July 2013 (UTC)

GAR

Lithium, an article that you or your project may be interested in, has been nominated for an individual good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article.--FutureTrillionaire (talk) 00:02, 27 July 2013 (UTC)

(H₂N(CO)NH₂) and mercaptans

Could someone, preferably with some knowledge of biochemistry, please take a quick look at this talk page query? If the user is correct, the article needs to be reworded, but this is way outside my sphere of competence. Rivertorch (talk) 18:57, 29 July 2013 (UTC)

OK I reworded it.--Livermorium (talk) 03:25, 30 July 2013 (UTC)

Thanks to you and to the others who followed. Rivertorch (talk) 05:20, 30 July 2013 (UTC)

Lycopodium stuff

Can someone look at 10-Hydroxy Lycopodium Alkaloids and File:10-Hydroxylycopodine, Deacetylpaniculine and Paniculine.jpeg ? These are out of shape (and the permission required for the file is missing) -- 76.65.128.222 (talk) 01:18, 12 August 2013 (UTC)

Someone with experience in copyright is needed here. The structures are PD-chem but the image itself includes the retrosynthetic analysis used to support the synthesis and appears lifted direct from the journal website. Perhaps it would be easiest to re-draw it as an .SVG? EdChem (talk) 14:39, 12 August 2013 (UTC)

AfC submission

Please have a look at this submission. Regards, FoCuSandLeArN (talk) 17:41, 12 August 2013 (UTC)

• looked at it, offered suggestions, needs work V8rik (talk) 20:47, 12 August 2013 (UTC)
• Another option is to put the content in cerium(IV) oxide. --Kkmurray (talk) 14:25, 13 August 2013 (UTC)

Classroom project

Hello WikiProject Chemistry. User:UMChemProfessor was requesting a course instructor user right at WP:ENB. Have people been happy with the progress of their student's work? (See the user page.) Just checking. Thanks. Biosthmors (talk) 21:01, 14 August 2013 (UTC)

I've seen some good results (in terms of content and on-wiki collaboration). DMacks (talk) 09:41, 15 August 2013 (UTC)

Spelling of decene

This word is ridiculous! In decane, the c is pronounced like a k the way we would expect. If decene is pronounced this way, it should be spelled dekene. C before e is soft. Georgia guy (talk) 18:42, 15 August 2013 (UTC)

That's two pretty big assumptions there! If decene is pronounced that way, and if words were either always pronounced the way they are spelled or were systematic based on pronunciation). I've often heard it pronounced with a soft c, and hard and soft C notes many exceptions to "C before e is soft". IUPAC (and others) usually are systematic by spelling (written form)--otherwise we wouldn't still have the names fluorene and fluorine as two different chemicals. DMacks (talk) 19:02, 15 August 2013 (UTC)

Category:Chemical compounds found in animals

Just to let you know: I nominated the above category for deletion. In addition, there in an ongoing CfD on Category:Phenolic compounds found in castoreum. --Leyo 13:23, 15 August 2013 (UTC)

Since there was consensus on deletion on these two categories, I think we may move forward and have a closer look at other categories in Category:Biomolecules by type of organism, which have similar issues. What about Category:Chemical compounds found in Eukaryotes‎ and Category:Chemical compounds found in Prokaryotes‎, incl. their subcategories? --Leyo 07:20, 22 August 2013 (UTC)

Also subcategories of Category:Chemical compounds found in food. There trick will be to group them appropriately. --Kkmurray (talk) 21:00, 22 August 2013 (UTC)

I am not sure if I understand what you mean by grouping. For a follow-up CfD? Or in a new category? --Leyo 22:31, 22 August 2013 (UTC)

Do you want to nominate all X compounds found in Y or split by Chemical compounds found in Y, Phenolic compounds found in Y, etc? --Kkmurray (talk) 03:56, 23 August 2013 (UTC)

{{Science}}

FYI, there's a note at WT:PHYSICS about a discussion at template talk:Science concerning Template:Science (edit | talk | history | links | watch | logs) -- 76.65.128.222 (talk) 06:07, 23 August 2013 (UTC)

Template:Hydrocarbons

I modified this template translating from Italian. Is that fine? --Daniele Pugliesi (talk) 08:35, 26 August 2013 (UTC)

Seems unwieldy and hard to maintain because it contains every specific chemical rather than just the categories/types (contrary to recommendations (Wikipedia:Navigation templates#Navigation templates provide navigation within Wikipedia says to keep small, focused, and directly related, not comprehensive; is against #3 and #4 of WP:NAVBOX guideline). As an example of the problem, it's already missing multiple entries. Navboxes shouldn't try to replicate the entire Categories structure-tree for chemical entitites. DMacks (talk) 09:16, 26 August 2013 (UTC)

Plural names for classes of compounds

In the Italian WikiProject Chemistry we agree to use the plural form for all the classes of organic chemical compounds, because in this case the subject of the page is referred to all the compounds of the class as a whole, instead of a single compound only.
Moreover, the introduction of these type of pages in general contains the plural form (e.g. the introduction of Polycyclic aromatic hydrocarbon is "Polycyclic aromatic hydrocarbons (PAHs), also known as poly-aromatic hydrocarbons ...").
If you agree and you want to follow this criteria in en.wikipedia also, the following pages for example need to be moved:

• Aliphatic compound --> Aliphatic compounds
• Aromatic hydrocarbon --> Aromatic hydrocarbons
• Unsaturated hydrocarbon --> Unsaturated hydrocarbons
• Polycyclic aromatic hydrocarbon --> Polycyclic aromatic hydrocarbons

To facilitate the renaming procedure, in it.wikipedia we created a category called "Classi di composti organici" (that means "Classes of organic compounds"), so we know that all the pages inside that category need to have the title with the plural. --Daniele Pugliesi (talk) 08:55, 26 August 2013 (UTC)

The chemistry standard is Wikipedia:Manual of Style/Chemistry/Compound classes. Although it gives examples of classes as plural-compounds, points to actual articles that are singular. The wider standard is Wikipedia:Naming conventions (plurals), which recommends plurals for classes of things when writing about the class as a whole as an exception to the universal WP guideline of using singular. To play devil's advocate, couldn't we just as easily fix it by saying A polycyclic aromatic hydrocarbon (PAH), also known as a poly-aromatic hydrocarbon ...? DMacks (talk) 09:06, 26 August 2013 (UTC)

(edit conflict)The previous trend was to use appropriate descriptors in brackets following the singular in ambiguous cases such as in Silane (class). The new trend is to use the plural Silanes vs. Silane, but this is only in ambiguous cases, in non-ambiguous cases the singular is preferred. Plasmic Physics (talk) 09:08, 26 August 2013 (UTC)

Good point about chemicals vs classes. Some articles cover both together, so "plural class" would contradict "singular specific entity".2,5-Diketopiperazine for example. In chemistry, this seems like one of the natural article-growth patterns (have a chemical, then start making derivatives). Keeping the class singular by default (until there is ambiguity due to splitting the class and parent-entity to separate articles) is easier to handle. DMacks (talk) 09:24, 26 August 2013 (UTC)

I have always disliked mishmash articles, where it is unclear if the main subject is the individual compound or the class. There may be information on the class in an article about an individual compound, but this needs to be stated as such (e.g. in a specific section).

In de-WP, articles on classes are consistently plural. --Leyo 09:57, 26 August 2013 (UTC)

Chemical compounds found in animals subcategories

I nominated the subcategories of the recently deleted Category:Chemical compounds found in animals for deletion at Wikipedia:Categories for discussion/Log/2013 September 1. --Kkmurray (talk) 04:10, 1 September 2013 (UTC)

Standard enthalpy change of combustion

Standard enthalpy change of combustion duplicates Heat of combustion. I suggest that these articles are to be merged. As heat of combustion is still a much more common term, standard enthalpy change of combustion could be redirected to it. --Fedor Babkin (talk) 05:14, 3 September 2013 (UTC)

AfC submission

Care to have a look? Wikipedia talk:Articles for creation/Paramenthane Hydroperoxide. Regards, FoCuSandLeArN (talk) 16:31, 9 September 2013 (UTC)

Images of radioactive materials

file:Polonium.jpg and File:Radon.jpg are up for non-free content review. As this revolves around issues of radioactivity, this may impact on images used by this project. -- 70.24.244.158 (talk) 13:27, 11 September 2013 (UTC)

Chemical element and simple substance

Although the terms "chemical element" and "simple substance" are often used as synonymous, they aren't!
In fact a "simple substance" is a chemical substance formed by atoms of the same chemical element. In other words, the "chemical elements" are not atoms neither materials. They are instead the names that define a "typology" of atoms.
Chemical element are simply the abstract classes of atoms defined by the periodic table, while the chemical substances are real aggregates of matter.
For this reasons, for simplicity we can use "chemical element" as a synonymous of "simple substance", but I suggest to clarify this difference between the meanings of these two terms at least in the pages Chemical substance and Chemical element. --Daniele Pugliesi (talk) 13:39, 12 September 2013 (UTC)

Zn, Cd and Hg poor metal

There is the discussion at the Wikiprojects Elements to make the elements zinc, cadmium and mercury poor metals, for me this looks strange. I could not find any of my chemistry text books (German) doing so. Is this only for me strange or is this referencable from anywhere? --Stone (talk) 09:10, 14 September 2013 (UTC)

Deletion of categories Chemical compounds found in foo and Phenolic compounds found in bar

Category:Chemical compounds found in Acanthaceae and related categories of the form Chemical compounds found in foo and Phenolic compounds found in bar have been nominated for possible deletion. If you would like to participate in the discussion, you are invited to add your comments at the category's entry on the Categories for discussion page. These are the plant, food, etc. categories similar to the Chemical compounds found in animals categories that were recently deleted.[3] --Kkmurray (talk) 17:04, 21 September 2013 (UTC)

The originating editor of this silliness, User:NotWith, should be warned for un-constructive editing. --Smokefoot (talk) 19:36, 21 September 2013 (UTC)

Wikimedian-in-Residence at the Royal Society

The Royal Society, the UK's science academy, is recruiting a Wikimedian-in-Residence to help them work more closely with Wikipedia. The position is part-time (one day per week) for a fixed term of 6 months. See here for more information and details of how to apply. For additional information please contact me at francis.bacon [AT] royalsociety.org Andeggs (talk) 14:12, 23 September 2013 (UTC)

CPhos

I am writing my first wiki page: https://wiki.riteme.site/wiki/User:Stevesnee/CPhos

However I can't seem to upload a decent quality molecular structure. Can anybody please explain how to do it using accelrys and any other standard / free software?

I have read the following guide: https://wiki.riteme.site/wiki/Wikipedia:Manual_of_Style/Chemistry/Structure_drawing

This seems to suggest that the diagram must created, printed and then scanned back into the computer. Can this be correct?

Any help would be much appreciated, Stevesnee (talk) 18:03, 24 September 2013 (UTC)

The article looks fine to me. Nice to see a new article be short and sweet for a change. My advice is to please spare us "decent quality molecular structure." The ChemDraw is sufficient. Congratulations on a nice start. --Smokefoot (talk) 22:54, 24 September 2013 (UTC)

Borane new article

The introduction of a new article borane on the monomeric BH₃ compound has meant that the previous article borane (a family article giving an overview of polyhedral boron compounds) has been renamed to boranes. It has dropped from google (why?) so I think a new name is in order, any ideas? Axiosaurus (talk) 11:26, 26 September 2013 (UTC)

I recommend reverting to boranes, and acknowledging that BH3 monomer is an esoteric entity, hence this species being subordinated into the larger one. Creation of borane is a case where one editor's well intentioned but misguided hair-splitting interferes with our mission of making chemistry acceessible.--Smokefoot (talk) 13:05, 26 September 2013 (UTC)

It's certainly an interesting chemical and the approximate key reactant in other complexes that themselves have articles. Could centralize any redundant commentary a bit. But the article-naming change is even worse than WP:PRIMARYTOPIC ideas. There are over a hundred inbound links to "Borane", which have existed since when the article was about the class and a spot-check finds many do want the class. I guess that's always the problem when splitting a unified topic into two separate ones. Will need to check and update them as necessary once it's decided which article gets which title. DMacks (talk) 14:48, 26 September 2013 (UTC)

What about moving boranes to boron hydrides and correcting all the links? boron hydrides redirects to diborane which makes no sense. --Bduke (Discussion) 20:58, 26 September 2013 (UTC)

'Boranes' gets more than triple the Google search result, than does 'boron hydrides'. Plasmic Physics (talk) 01:51, 27 September 2013 (UTC)

So? That Google test is useless anyway. Revert please and merge any data into the original. --Dirk Beetstra ^{T C} 11:46, 27 September 2013 (UTC)

Why? As far as I know, contentious mergers require consensus, and there appears to be a lack of it here. FYI, 'Borane' was never split from 'boranes', it was created from scratch. Plasmic Physics (talk) 13:35, 27 September 2013 (UTC)

Please revert recent changes. Many articles exist describing derivatives in the context of the parent compound. Far reaching edits should be discussed first. In addition I understand the internal linking has been handled in a sloppy way. V8rik (talk) 16:07, 27 September 2013 (UTC)

Hmm, not sure I agree with reversion at this stage. Yes, molecular BH₃ has only a transient existence, but it has been detected in the gas phase, and B-H bond length determined experimentally. It is believed to be an intermediate in the pyrolysis of diborane to form higher boranes, and kinetic studies indicate it to be an intermediate in hydroboration reactions. Where an article could be useful would be in collecting BH₃ adduct and reaction intermediate chemistry. The current borane article is still in its infancy, I am having a friendly debate there with user:Plasmic Physics about content. I believe it needs to evolve before it is considered for merge, and that begs the question "merged with what?" Diborane? optimistically rated as B class in my view and anyway adducts do not always involve diborane as a starting point or as an intermediate, but that said it would be a better choice than boranes, which would be a strange mix in my view as that article struggles to deal with the plethora of higher boranes as it is, and doesn't need diluting.Axiosaurus (talk) 11:07, 29 September 2013 (UTC)

Pun intended (borane is only used in dilution)? Plasmic Physics (talk) 12:44, 29 September 2013 (UTC)

Axiosaurus, you can try if you wish. My sense is that Plasmics understanding of chemistry is often weak or just weird. Fortunately, he has mainly edited on fringe topics like copper hydride (even that was a headache), but borane is more core material that impacts on wider readership. One gets this kind of eye-rolling edit: "Gaseous borane, diborane(6), is a hydrophilic (non-polar) aprotic solute... This dissolution property of borane makes it a widely used laboratory chemical ..." The dissolution property is the reason that BH3 is useful? Really? It is useful because it dissolves? BH3 is nonpolar in THF? If you can serve as mediator/mentor/warden, we could look forward to smoother relations and better edits. To push my luck, one suggestion would be to pre-announce major revision projects. --Smokefoot (talk) 13:44, 29 September 2013 (UTC)

I concur with Smokefoot, if Axiosaurus sees merit in this venture who am I to complain V8rik (talk) 19:43, 29 September 2013 (UTC)

Yes, really, if borane was not readily soluble, it cannot be stabilised, and that would mean it would be chemically useless, based on its fleeting existence in an unsolvated state. Plasmic Physics (talk) 22:07, 29 September 2013 (UTC)

Aromatic SMILES

A claim (see User talk:Dvwynn) has been made that lowercase aromatic symbols in the SMILES specification (1) has been deprecated and (2) does not work in several chemical GUIs (Reaxys, SciFinder). While changing aromatic to Kekulé SMILES is probably harmless, before making large number of changes to SMILES strings in articles, it would be wise to first obtain consensus. Are there any opinions on what the preferred SMILES format should be? Boghog (talk) 20:29, 30 September 2013 (UTC)

I don't know about the GUIs, but the lowercase alternative for indicating aromaticity in the OpenSMILES specification doesn't say anything about deprecation and recommends that the lowercase alternative is preferred for output, because there is no ambiguity in the single and double bond assignments. --Mark viking (talk) 20:50, 30 September 2013 (UTC)

Boghog noted on User talk:Dvwynn that Reaxys does seem to accept the lower-case notation. I just tried "Cc1c(C)cccc1" in SciFinder's drawing module, and it drew o-xylene. It gave me alternating single/double bonds because that's how SciFinder's entries seem to be, but at least "the SciFinder GUI works" for it, and I don't see any way to search more directly using the SMILES string. DMacks (talk) 11:28, 6 October 2013 (UTC)

Thanks DMacks for verifying that the lower-case notation works in the SciFinder GUI. Hence it appears that the justification for these changes is faulty (as far as I can tell, the lower-case notation is not deprecated and the lower-case notation does work with Reaxys and SciFinder). Boghog (talk) 15:53, 6 October 2013 (UTC)

Chem box (again!)

I am still concerned about the intrusive nature of some of the large Chem boxes. If nothing else, they can interfere with the layout, particularly with the showing of images. See, for example, ascorbic acid. Besides, there is no need to show all this data up front.

The chembox documentation suggests moving some of the information on to a data page. I have tried out a variation on this theme with the topic ethanol for which ethanol (data page) already exists. I simply copied the whole of the existing chembox on to the data page. Then, I removed all but a few items from the chembox on the article page. This results in a chem box on the article page of reasonable size, with all the original data being only one click away on the supplementary data page. The same process can be applied to other boxes like elementbox (vanadium), drugbox (aspirin). Others?

The choice of what to retain is obviously a matter for which consensus should be reached. I suggest we delay that process and concentrate initially on whether or not this change is a good idea, or not. Petergans (talk) 14:52, 6 October 2013 (UTC)

What should be displayed in a infobox in a given article is somewhat subjective and I think needs to be considered on a case by case basis. Just because a field exists in an infobox doesn't mean it must be used in every article. In the ascorbic acid example, IMHO listing the solubility in different solvents is excessive. Displaying the solubility in one solvent (water) should be more than sufficient. The rest could be moved to a separate data page. In addition, the value of a 3D display of one arbitrary conformation of a flexible molecule is questionable and IMHO amounts to little more than eye candy. Boghog (talk) 15:48, 6 October 2013 (UTC)

I agree about the 3-D display, but there is a problem - there is no visible entry that can be edited out of the chembox. In fact, the only way to remove it is to remove the SMILES item. I can't edit the template itself (the page is permanently protected), so I don't know where this problem comes from. Worse still, it does not work! When I click on the image1 link I get the error message "ERROR opening http://cactvs.nci.nih.gov/chemical/structure/CCO/file?format=sdf&get3d=True -- CCO could not be loaded." Petergans (talk) 09:55, 7 October 2013 (UTC)

A US government website not working this week is most likely a problem with the Republicans having turned it off. Not something that WP can fix. Andy Dingley (talk) 10:43, 7 October 2013 (UTC)

COI editing

I have noticed an upsurge in edits by infrequent editors who seem only to come to Wikipedia to insert citations to their own work or at least work by one team of researchers. In the past, I have left a message at their talk pages as follows:

==Welcome, but be careful==

Welcome to Wikipedia. Here are suggested readings: [[WP:SECONDARY]] and [[WP:COI]]. The gist of these guidelines are:

• Wikipedia prefers citations to reviews and books, ''not'' primary journal references (tens of thousands appear annually). Citing secondary sources is the encyclopedic style.
• Do not cite yourself or your colleagues. It's called conflict of interest. Many new editors cite themselves mainly. That behavior is inappropriate.

Editors like me are wary when we observe a new editor such as yourself citing repeatedly work by one team, it seems to be likely COI. If you have questions, many editors can offer advice. Happy editing.--~~~~

We are supposed to be welcoming to new editors, and I strive to follow that guideline, but this self-citation behavior seems usually, not always, to be inappropriate. But maybe the community does not agree with my actions in which case I welcome discussion. I fear however that articles will become filled with the latest "vanity citations". On the other hand, content is content, which gives me pause. A recent example of the behavior that I am referring to are the recent chem entries here.--Smokefoot (talk) 04:26, 8 October 2013 (UTC)

RFC on Elements infobox

Hi chemists, please stop by this RFC on modifying the icon images in the Elements Infobox: [4]

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

"Molecular mass"

Could someone help clean up this article? It's quite sad that something as essential as molecular weight has such a poor quality article to describe it. My immediate concerns are summarized on the article talk page. Thanks. (+)H₃N-Protein\Chemist-CO₂(-) 10:49, 29 August 2013 (UTC)

Guess no one shares my concerns? (+)H₃N-Protein\Chemist-CO₂(-) 10:41, 16 October 2013 (UTC)

Chalcogen assigned to Chemistry Project

I have added the article chalcogen to the Chemistry project, currently it is marked up as Project Elements and an enthusiastic group of editors is pushing it on. It has been rated as GA. The chemical compounds section lets it down. IMHO it requires either drastic improvement and enlargement in terms of detail or a complete rethink and rewite to highlight chemical trends. Of all the groups this must be one of the most difficult to tackle as O is so different from S, Se and Te and Po is different again, which is of course why most text books treat oxygen as a separate topic from the rest of the group.Axiosaurus (talk) 11:37, 19 September 2013 (UTC)

It is very difficult to write a decent article mixing O and S/Se/Te. Enthusiasm often trumps competence, unwittingly and with good intentions. --Smokefoot (talk) 13:34, 19 September 2013 (UTC)

I think that the page Chalcogen contains too much informations, because these elements do not show so much similarities, so it make no sense for example to write a section about the history or about the compounds of chalcogens putting into it the informations of each element and try to mixing everything together in an heterogeneous way. It looks to me like a patchwork! --Daniele Pugliesi (talk) 22:28, 19 September 2013 (UTC)

Considering that this is an article about group 16 elements, there is a glaring deficiency - the absence of any discussion of trends withing the group (periodic trends). I'm too busy at the moment to address this issue. A good starting point might be Greenwood & Earnshaw, p784 "Chemical reactivity and trends"[in group 16]].Petergans (talk) 10:03, 6 October 2013 (UTC)

This article is now up for FA review. OMG! It has not been changed since I highlighted it here. You might like to comment, Wikipedia:Featured_article_candidates/Chalcogen/archive1. How this ever got to GA defeats me.Axiosaurus (talk) 07:46, 18 October 2013 (UTC)

Kids will be kids. One needs to anticipate emerging or missing articles and write them in a way that orients future editors and aims to inform readers. Otherwise these topics get misoriented. --Smokefoot (talk) 12:18, 18 October 2013 (UTC)

Zinc and the common cold

The zinc article and the Zinc and the common cold article are edited by a person with a near identical user name to the added references. This might be COI or good work I can not find out in short. If somebody want to have a look or help?--Stone (talk) 20:11, 24 October 2013 (UTC)

aurum fulminans

Colleagues, currently Aurum fulminans redirects to Fulminate. However this redirect seems to be incorrect. Quoting from Peter Krehl's History of Shock Waves, Explosions and Impact, p. 200:

"In 1608 Oswald CROLL, a German physician and iatrochemist ... first describes the preparation of aurum fulminans (“fulminating gold”). More important than the function of aurum fulminans as a putative medicament was its usefulness when investigating the nature of combustion... Although aurum fulminans was derived from a nitrous agent, it was not clear what part the aqua fortis (“nitric acid”) played in its formation. It provided, therefore, an ideal control for experiments to test theories which purported to explain the explosion of gunpowder. Robert BOYLE found that its action differed significantly from that of gunpowder, in that it could be ignited in a vacuum by both a burning-glass and a hot iron.

Fulminating gold (ClAuNH2)2NH is prepared from gold chloride and aqueous ammonia. Note that fulminating gold is distinct from “gold fulminate.” Gold fulminate (gold hydrazide, AuN2H3) is a water-soluble olive-green powder and more explosive. Unlike conventional gunpowder, it explodes violently when dry and exposed to friction, shock and heat, and so is obviously the first very sensitive man-made high explosive (“exploding gold”). Gold fulminate is a salt of fulminic acid (C2H2N2O2) − in Germany appropriately called Knallsäure (“bang acid”) − which was discovered in 1824 by Justus VON LIEBIG." --Fedor Babkin (talk) 13:42, 15 October 2013 (UTC)

Your basic premise seems to be correct. If so, fulminating gold needs a separate article. However, there is a problem with trivial names. Fulminic acid , HCNO, is logically the acid from which the fulminate ion CNO^- is derived. Knallsäure, which you state has the formula C₂H₂N₂O₂ is a different acid, or is it? Does it have a trivial name in English? I have found this review: http://publik.tuwien.ac.at/files/PubDat_170506.pdf Petergans (talk) 08:21, 16 October 2013 (UTC)

Isn’t one of those the empirical formula, and the other the molecular formula of the dimer? ISTR nitric oxide being like that, variously given as either NO₂ or N₂O₄.—Odysseus1479 05:22, 25 October 2013 (UTC)

Proposed merge: Light-activated resin to Photopolymer.

Proposed merging Light-activated resin to Photopolymer. Same thing, but dentists and stereolithography people use different terminology. Both articles are brief, under-cited, and could use some attention. Please discuss at Talk:Photopolymer. Thanks. --John Nagle (talk) 20:46, 25 October 2013 (UTC)

It turns out there's also Photopolymerization, which is just a link to polymerization, cross-link, on how polymers cross-link, and Stereolithography#Technology. Amongst all these articles, nowhere is there a clear explanation of how ultraviolet light turns a gel into a solid. There should be, and then we can link everything else to there. I'm not a chemist; this needs someone who is. --John Nagle (talk) 19:40, 26 October 2013 (UTC)

AfC submission

Could you go over this submission and this one? Thanks! FoCuSandLeArN (talk) 17:45, 5 October 2013 (UTC)

• Another one for you. FoCuSandLeArN (talk) 11:38, 28 October 2013 (UTC)

Wikipedia talk:Articles for creation/P-hydroxynorephedrine

As requested, I am reporting a chemistry-related submission at Afc. Would someone here like to review it? We have a backlog of over 1400 submissions right now; any help would be appreciated. —Anne Delong (talk) 03:28, 25 October 2013 (UTC)

I just put up - I figured I'd do the AFC route since I'm not 100% sure I had conformed to chem MOS (ex. on article names and use of a dbox) - just for reference for whoever reviews it, I used P-hydroxyamphetamine as a template due to their relationship. Technically WP:Pharm/med-related too due to the fact that it's an Rx-drug metabolite. Regards, Seppi333 (talk) 03:55, 25 October 2013 (UTC)

One more: User:Seppi333/P-hydroxyphenylacetone. Thanks Seppi333 (talk) 17:37, 28 October 2013 (UTC)

Bent's rule rewritten

I have done a major rewrite of Bent's rule, an article that was previously a "C-Class" article of "High-importance" in this WikiProject. I am still actively working on it, but I would appreciate any feedback you might have. Thanks. B Levin13 (talk) 19:58, 3 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) 17:38, 19 November 2013 (UTC)

International Year of Crystallography 2014

UNESCO proclaimed the "International Year of Crystallography 2014". It can be an important opportunity for wikipedians to contribute in an international initiative, spreading the scientific knowledge, in particular about crystallography.
These are my proposals to participate to this event:

• to create the page International Year of Crystallography 2014 in all the Wikipedias
• to improve substantially during this year the page Crystallography, Crystal and other important pages about crystallography, in all the Wikipedias
• to create and translate pages related to crystallography
• to create a Portal:Crystallography
• to organize better the pictures in commons:Category:Crystallography and encourage the creation of new pictures
• to contact all the Wikipedias, other Wikimedia projects, Wikimedia Foundation and the organizing committee of the "International Year of Crystallography 2014" (here you can see their contacts) to communicate our adhesion to this initiative.

Do you have any other opinion or suggestion? --Daniele Pugliesi (talk) 10:12, 20 November 2013 (UTC)

Good suggestions! I'm not a crystallographer myself but do sometimes want to put structures into Wikipedia articles - see the discussion on #structures above. It would be useful to have a list of Wikipedia editors who have access to the Karlsruhe and Cambridge databases. Petergans (talk) 14:21, 20 November 2013 (UTC)

any interest on analytical reference data for chemicals?

I just want to ask if there is an interest to link analytical reference data such as reference spectra for gas chromatography - mass spectrometry (GC-MS) from the WikiPages of certain chemicals. For example: this spectrum for Alanine could be linked from the Wikipedia page for Alanine. I appreciate any comments on that! Best regards, Jan — Preceding unsigned comment added by Jahu54321 (talk • contribs) 09:56, 15 November 2013 (UTC)

Yes spectra would be welcome. Ultimately with assignments. Priorities might be various NMRs, followed by IR, then UV-vis, then EI-MS. Dreaming further, TGA and calorimetry. The list doesn't end. Ideally such spectra would not be linked to a company or such that distracts readers from content for the sake of content. --Smokefoot (talk) 14:00, 15 November 2013 (UTC)

• ideally, if you have spectra that are of interest to Wikipedia (they are!), upload them to wikimedia commons with proper attribution. V8rik (talk) 16:31, 15 November 2013 (UTC)
  

Smokefoot and V8rik, thank you very much for your reply. I write here in my function as lead developer of the Golm Metabolome Database (GMD, http://gmd.mpimp-golm.mpg.de) which is hosted at the Max Planck Institute of Molecular Plant Physiology. Of course I understand your wish that all spectra get uploaded to Wikimedia. But let me put it like this, according to the GMD terms and conditions there is no way to upload/display the spectra to/on Wikipedia pages as the re-distribution is explicitly excluded in the GMD terms and conditions. This spectra are as free as they can be, as long as they remain on the GMD website. There was a considerable investment in terms of money and time which must be attributed to the GMD. We also developed a set of tools which are essential to visualise spectra online. Ultimately, even further down your wish list you want to know the normal concentration values of your chemicals across body fluids or biological samples. You won’t integrate all this details into Wikipedia. I assume somewhere a break where you plainly need to out-link to specialised databases such as the GMD.

What I would like to propose is a system/arrangement where this spectra remain on the GMD web site and Wikipedia links-out to this single spectra pages as it does in many other cases too, i.e. for general references / publications. This way, a potential user would only need one click to come from the chemical information on Wikipedia to the reference spectrum on the GMD site. Of course this use-case would not be specific to GMD’s GC-MS reference spectra. There are many more specialised databases, i.e. the Human Metabolome Database having NMR spectra or MassBank providing mass spectra and many others databases to come. If you would have any idea what is worth to be improved on the GMD spectra pages I would appreciate this feedback very much.

Is there still some interest? Jahu54321 (talk) 22:50, 15 November 2013 (UTC)

understandable of course, I have added an external link to the mass spectrum of alanine on the analine page, that should do the trick, lets see what the community thinks about this edit. V8rik (talk) 22:05, 22 November 2013 (UTC)