Wikipedia talk:WikiProject Chemistry/Archive 40

Nitration
Maybe I am missing something, but Wikipedia seems to have no or few categories relevant to nitration or related reactions. Or perhaps the categories favor compound types vs reaction types. --Smokefoot (talk) 16:06, 17 August 2016 (UTC)
 * Wikipedia has many more articles about chemical compounds than about chemical reactions, so more chemical categories than reaction categories are needed for reasonable organization. There are hundreds of articles in Category:Nitro compounds and its subcategories, but if Category:Nitration reactions were to be created, would there be anything to put in it aside from Nitration?  -- Ed (Edgar181) 16:42, 17 August 2016 (UTC)
 * Agree, that category type would remain rather empty V8rik (talk) 18:01, 17 August 2016 (UTC)
 * Yes, it would be a rather short list, but there are a few other things one could place in it. In addition to nitration (ionic), one could add free radical nitration, Menke nitration, Zincke nitration, reactive nitrogen species, and nitrotyrosine. Boghog (talk) 19:33, 17 August 2016 (UTC)
 * If someone ever adds a page for the Reverdin rearrangement (a.k.a. Reverdin reaction) that can also go in the new nitration reactions category, alongside the Wolffenstein–Böters reaction and some of the examples above. BiomolecularGraphics4All (talk) 10:28, 29 August 2016 (UTC)
 * Likewise, if Ponzio reaction was given its own page (split out from Oxime) it would also be in Category:Nitration reactions BiomolecularGraphics4All (talk) 10:21, 30 August 2016 (UTC)

Christopher J. Schofield
For a number of days the article Christopher J. Schofield is hanging around on the list "Articles With Multiple Dablinks". I have taken a look at it, but it is too much for me. Can somebody take a look at the article and solve the 5 links to disambiguation pages?

These are the culprits:
 * 1) Histone demethylase
 * 2) Hypoxia
 * 3) Inhibitor
 * 4) Kinetics
 * 5) Synthesis

Thanks in advance! The Banner talk 21:48, 31 August 2016 (UTC)
 * ✅ EdChem (talk) 06:49, 1 September 2016 (UTC)
 * Thank you very much! The Banner talk 09:09, 1 September 2016 (UTC)

Articles for deletion/Quasi-elemental
I wonder if any chemists might be willing to offer a view? Thanks! Josh Milburn (talk) 04:37, 3 September 2016 (UTC)
 * This article has nothing to do with chemistry. Sandbh (talk) 08:06, 3 September 2016 (UTC)
 * I think the question Josh is asking is, in the event that the AfD is closed as 'merge' (as seems reasonable at the moment), should the page quasi-elemental be a redirect to the merge target or be pointed at some chemical / scientific target? I agree with Sandbh that the current content has nothing to do with chemistry, but a google scholar search linked at the AfD suggests the term "quasi-elemental" is used in the scientific literature at times.  EdChem (talk) 09:39, 3 September 2016 (UTC)

Deuterium in the chemical formula
To enter a chemical formula in Infoboxes Chembox and Infobox drug, they have the option to use. (using Chem and straight HTML-text is possible too). An editor asks that the parameter D (Deuterium, or 2H) be added, to make possible C11H15D2NO3 (Beta-D) to be entered that way. (Additional advantage is that the molecular mass can be calculated from these individual entries).

We could add "D" as an element symbol. I'd like to learn if there are any pitfalls or errors when doing so. -DePiep (talk) 14:03, 27 June 2016 (UTC)
 * Thanks for posting it here. From what I've read on WP:MOSCHEM, D should be allowed just fine. No other element appears to have that same symbol, so there shouldn't be any complications. The very few deuterium containing compounds with articles on Wikipedia included "D" in their formulae for many years, the only difference this change would cause is making it possible to be used via the shortened input form that also calculates the molar mass. Aethyta (talk) 14:47, 27 June 2016 (UTC)
 * (quoting here:) CIAAW recommends 2.0141017781 for atomic mass.
 * And this: the formula uses Hill system: "when C is present, put any C, H in front". (ie, it is organic. Note that this is about the simple, empirical formula. When structure is in the formula, like groups, do not use this input form. Better use chem or HTML). Should we treat D alike, ie, in front with C? Why not? -DePiep (talk) 20:18, 27 June 2016 (UTC)
 * I think D and T should be sorted as though they were H. Notice that IUPAC specifically recommended 2H and 3H as symbols (though accepting D and T) to preserve sorting, so this seems the best option. I can't imagine myself writing "CClD3"; it feels so wrong. Double sharp (talk) 17:00, 3 September 2016 (UTC)

Addition of new Refrigerants to the list of refrigerants wiki.
Anyone here willing or capable of adding some of the new refrigerants to the list, The reason I am asking this is due to the new F-gas regulations in Europe and North America are making it a relevant topic Some of the new Refrigerants:

-R448 -R449

And other new HFO blends below 1500 GWP.

With best regards.

Curious Tech 83.150.90.40 (talk) 12:04, 7 September 2016 (UTC)

MSDS, data pages
Hi. An editor was going through chemical articles adding ELs to the MSDS and tech specs from a single company and I reverted them as spamming. They left a note on my talk page saying they were looking to do this across many many more chemical articles, and I referred them here. They found some old discussions; I looked too, and it isn't clear to me what you all are doing now. The user seems to have chickened out from asking you all, so here I am. I run into some of this on drug articles I work on.

I looked at Sodium chloride and its associated Sodium chloride (data page) and MOS:CHEM as well as WP:MOSCHEM/SAFE (and i just now saw the discussion of MSDS at the bottom of that page, here and i totally get what it says there - it was one thing bothering me about the edits I reverted)

MOSCHEM doesn't mention "data page" at all; is creating these still your current practice?

It seems that for each article, you fill out the Template:Chembox and fill out the associated data page (?) but it is not clear to me where that data is actually coming from... sources aren't cited for everything. Are you actually using MSDS' for that data?

I can kind of understand where that editor was coming from, as sources for data in the chembox aren't clear to me. Where is it coming from?

Thanks! Jytdog (talk) 01:07, 15 September 2016 (UTC)
 * Jytdog If you look at the bottom of the infobox for chemical, you can see "Infobox references". By clicking on it, you are redirected towards the references section.
 * For the data pages, it is an old feature which not more used and recommended. Mainly because there were no references and no structure.
 * Then, this is my personal opinion, we should move from the current structure towards a structure where each data in the infobox should be linked to its reference with a clear link.
 * Finally, I think Wikidata is the solution to your questions. People add there their data there and then you can extract the data you want by excluding MSDS data if you want. Snipre (talk) 07:56, 16 September 2016 (UTC)
 * Thanks for answering. Yes I reckon there is some syncing between WikiData and Chemboxes.   WikiData is, as far as I can see, a huge pile of unverified data.  I worry about it.
 * I struggle with the hand-wavy link to the references section, as a way to source all the data in any infobox.
 * as a nonmember of your project, i think it would be great if you all included some statements in your style guide about the defunct status of "Data pages"
 * Thanks again! Jytdog (talk) 17:03, 16 September 2016 (UTC)

Scifinder
looking for β-Hydroxyisovaleric acid(CAS # 625-08-1) information page on SciFinder but don't have access, this is for an FA article nominee, thank youOzzie10aaaa (talk) 12:53, 19 September 2016 (UTC)
 * 3-Hydroxy-3-methylbutanoic acid,3-Hydroxy-3-methylbutyric acid, 3-Hydroxyisovaleric acid, β-Hydroxy-β-methylbutyric acid, β-Hydroxyisovaleric acid
 * 1062 articles, patents, reports etc on this compound. 53 reviews.
 * Top cited reviews:

--Smokefoot (talk) 13:26, 19 September 2016 (UTC)
 * "Dietary supplements for body-weight reduction: a systematic review" By Pittler, Max H.; Ernst, Edzard American Journal of Clinical Nutrition (2003),  Volume Date2004, 79(4), 529-536.
 * "Nutritional role of the leucine metabolite β-hydroxy β-methylbutyrate (HMB)" By Nissen, Steven L.; Abumrad, Naji N. Journal of Nutritional Biochemistry (1997), 8(6), 300-311.

Calls to non-existent templates
Template editors, please see this note about Template:Reactionbox. – Jonesey95 (talk) 18:42, 28 September 2016 (UTC)

There is a redirect discussion of which members of this project could help.
Redirects_for_discussion/Log/2016_October_2 is ongoing. We are not sure whether "misfold" is a purely biochemical term or if it could WP:SURPRISE people who were looking for info about folding blankets. Your input would be much appreciated.--Mr. Guye (talk) 19:54, 2 October 2016 (UTC)
 * There are now two (consecutive) discussions at RfD – Redirects for discussion/Log/2016 October 2 and Redirects for discussion/Log/2016 October 2 – covering 13 different redirects with variations on the term "misfold". I suggest contributors from here comment in both discussions.  EdChem (talk) 23:00, 2 October 2016 (UTC)

Concentrated electrolyte solutions activity coefficient
Hello wikifellows! Can someone take a look at Activity coefficient and access the full text of the mentioned cited source for the formula present in article for the statistical part of the activity coefficient in order to add further details of its derivation? Thanks!--82.137.13.168 (talk) 15:42, 5 October 2016 (UTC)

Also, this source Trans Faraday Soc could also be relevant to the mentioned topic.--82.137.13.168 (talk) 16:03, 5 October 2016 (UTC)

Early transition metal pincer complexes
What should be done with this page, which [//en.wikipedia.org/w/index.php?title=Wikipedia:Early_transition_metal_pincer_complexes&diff=614646872&oldid=614646815 seems to have been moved into the wrong namespace]? Is it worth moving it to the main namespace? Graham 87 02:34, 10 October 2016 (UTC)
 * .. it appears to be about "Early 'transition metal pincer complexes'" (and not about the pincer complexes of the early transition metals). I think that this would be a welcome addition to the contents of Pincer complex, so my !vote is to merge.  --Dirk Beetstra T  C 05:56, 10 October 2016 (UTC)
 * I'll merge it in a couple of days unless others have alternative suggestions. --Smokefoot (talk) 18:11, 10 October 2016 (UTC)

Lolitrem B needs "translation"
Hello. Can someone please "translate" the above article so normal readers can understand somewhat what the article is about? I've added a tag to the article with the reason parameter filled in. While you're at it, you may want to fill in the data on the talk page, specifically the quality scale and importance scale ratings. I've already added the template, but left the parameters blank.  — Gestrid  ( talk ) 21:53, 9 October 2016 (UTC)
 * I've had a stab at the lead but as this is about a neurotoxin you might have better luck with someone from WikiProject Pharmacology --Project Osprey (talk) 09:24, 10 October 2016 (UTC)
 * Alright, I'll post on their talk page.  — Gestrid  ( talk ) 18:17, 10 October 2016 (UTC)

Multiple articles on one chemical
Hello, I have a small problem with a chemical, octopamine: en:WP is the only Wikipedia which does the difference between the drug (Octopamine (drug)) and the neurotransmitter (Octopamine (neurotransmitter)), all three articles having their own item in WD. This is your choice. But for WD this splitting is a problem because we don't want to do the differences between the possible uses: this is a chemical so all data regarding this chemical should be located at the same place.

Is it a problem if I merge all data in the item linked to octopamine and recycle the 2 other items for R- and S-octopamine ? The consequence of this action is the lost of items dedicated for the drug and for the neurotransmitter with the possibility to link to articles in other Wikipedias (but currently only WP:en is doing the distinction). Snipre (talk) 09:56, 10 October 2016 (UTC)
 * It's a deficiency of WD if there is no way to cope with different *.wp having different levels of subarticles vs only higher-level ones available. That said, in this case, I can see reason to merge since it really is the same topic. But but, is the neurotransmitter (in vivo/enzymatically produced) really racemic? And is the drug, which appears to derive from natural extracts, also racemic? I would still support a unified article about the chemical, but "the chemical" might need to be better-defined in order to have the subsection about...biochemistry and/or drug-application also chemically correct. DMacks (talk) 15:56, 10 October 2016 (UTC)
 * There are other articles that are split into two articles about the use of an endogenous compound as a drug and the compound in general (e.g., Norepinephrine (drug) and Norepinephrine). The latter article is usually the parent article of the former. In this case, octopamine (neurotransmitter) should probably be moved to octopamine, with a subsection added on the use of octopamine as a drug/pharmaceutical and a  link to octopamine (drug) in that section. IIRC the main reason for creating separate articles in both of these cases was to address a dispute about the use of  vs  as the article's infobox.  Seppi  333  (Insert 2¢) 18:27, 10 October 2016 (UTC)
 * This is not a deficiency of WD: WD can do what WP is doing. The problem is in the difference between WPs and in the splitting of data. The splitting implies that all people agree and know the splitting and how the data are shared between the different parts. If people don't agree about the splitting no system can solve that problem.
 * WD currently deals with the mixture of stereoisomers and each pure form of stereoisomer. So for the case of octopamine we have 3 items: octopamine (mixture of stereoisomers), R-octopamine and S-octopamine. Why ? Because for each item we can have unique identifiers like isomeric SMILES, InChI, InChIKey, CAS number,... These identifiers are objectives because based on physical rules. The difference between drug and neurotransmitter is not objective: if you are in front of two molecules of octopamine, can you say which one is the neurotransmitter and which one is the drug ?
 * How en:WP want to split its articles is not my concern, I just want to create in WD a logical splitting based on objective rules. Then if WP:en wants to link its Octopamine (neurotransmitter) article to the octopamine item or to the R-octopamine item, it is the choice of WP:en based on its criteria. Snipre (talk) 21:50, 10 October 2016 (UTC)
 * Thanks to show that the current splitting is not based on rational reasons. But if this is the choice of WP:en, I don't want to put pressure to change it. I just want to change the items on WD. The only consequence is the lost of the Wikidata item link in the toolbox on the left side of the article. As there is no interwikis, this doesn't have any consequence. Snipre (talk) 21:56, 10 October 2016 (UTC)

Sulph- to Sulf-
The international standard nomenclature is sulfur, and -f- for all usages (established over twenty years ago). So it makes no sense that many pages still link to Sulphur and Sulphuric acid, and there is no good reason to (see editorial in Nature Chemistry. It would be a relatively trivial manner for somebody's bot to automatically replace all references. TehAnonymous (talk) 16:41, 17 October 2016 (UTC)
 * Since there is a redirect in place, there is no real need to do it. The non standard form can still be used in non chemical/stry project article pages, or in quotes, or journal article titles.  There are quite a few places we should not change it.  So I would not let a bot loose on the job. But for chemistry articles you could have a look to see how big the change would be. In my opinion it is better to write some more content than to alter spelling between forms that are both equally understood. Graeme Bartlett (talk) 02:32, 18 October 2016 (UTC)

How do I join?
How do I join WikiProject Chemistry? — Preceding unsigned comment added by Wretertert (talk • contribs) 00:39, 16 October 2016 (UTC)
 * You can add your user name on WikiProject Chemistry/Participants. But it is optional, I am not there, but I still participate in discussions here, and edit Chemistry articles. There also a related project at WikiProject Chemicals. Graeme Bartlett (talk) 02:38, 18 October 2016 (UTC)

Good Article Reassessment of Calcium chloride
Calcium chloride, 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. BlueMoonset (talk) 04:43, 19 August 2016 (UTC)
 * It was demoted. Graeme Bartlett (talk) 02:42, 18 October 2016 (UTC)

Video downloads of chemical demo's
User: Kiril Simeonovski has added several videos of chemical reactions to articles. The aspect that worries me is that these videos download to my computer. So I wonder about infection of my machine. Kiril assures me that all is OK here, but reassurance from computationally adept editors would be welcome. Other aspects of these videos can be debated later.--Smokefoot (talk) 15:06, 20 October 2016 (UTC)
 * Hi Smokefoot, there's also a discussion about this at Village pump. Files provided by Commons should be perfectly safe for end users. As to the video automatically downloading, I'm not sure why exactly that would be the case. The videos in question play in the browser for me. I'd guess that your web browser doesn't know what to do with a WebM file, so it defaults to downloading it. If you use Firefox, this discussion may be of use. clpo13(talk) 17:35, 20 October 2016 (UTC)

Nomination for merging of Template:Acids
Template:Acids has been nominated for merging with Template:Acids and bases. You are invited to comment on the discussion at the template's entry on the Templates for discussion page. Thank you. Comfr (talk) 02:09, 24 October 2016 (UTC)

GA reassessment of Chalcogen
Chalcogen, 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. Double sharp (talk) 05:22, 25 October 2016 (UTC)

Nobel project: Chemistry - explainer video
Within the Nobel project we work on a script for an explainer video about the molecular machines. You're welcome to review the script and give us feedback. You can find the document here: https://commons.wikimedia.org/wiki/Simpleshow#Chemistry_-_2016-10-27 Thank you for your support! --Norma.jean (talk) 10:28, 25 October 2016 (UTC)

Free access to ECS digital library Oct 24-Oct 30
from my email: To promote Open Access Week 2016, from October 24 through October 30, ECS is taking down the paywall to the ECS Digital Library (http://ecsdl.org). Over 132,000 articles will be freely available to anyone who wants to read them. ECS is giving the world a preview of what complete open access will look like when we have completed our Free the Science (http://www.electrochem.org/free-the-science) campaign. A commendable effort! Let's help show ECS that full open access will be useful to Wikipedians :) -- phoebe / (talk to me) 13:42, 25 October 2016 (UTC)

RFCs on citations templates and the flagging free-to-read sources
See Headbomb {talk / contribs / physics / books} 16:13, 29 October 2016 (UTC)
 * Village pump (proposals)
 * Village pump (proposals)

RfC on the default display of group 3 in the periodic table
See Template talk:Periodic table (started by AzaToth). Double sharp (talk) 09:03, 30 October 2016 (UTC)

Energetically modified cement
Dear chemistry experts:

I came across this article which had been tagged for improvement. I have edited it extensively to make it more readable, add independent references, and to remove some opinion and peripheral material. However, I am not a chemist, so I am unable to deal with the section on the chemical reactions. Also, there appears to be some essay-like content which would be better culled by someone with a better understanding of the topic. Can someone here help?&mdash;Anne Delong (talk) 02:21, 31 October 2016 (UTC)
 * There are also some references which may be closely connected; however, I haven't been able to check them because the website (http://www.emccement.com) seems to be down right now, even though Google has indexed it.&mdash;Anne Delong (talk) 02:27, 31 October 2016 (UTC)

Infobox hydrogen at TFD again
is up for deletion again. Please discuss at Templates for discussion/Log/2016 October 30. -- Red rose64 (talk) 17:58, 31 October 2016 (UTC)

Frank R. Lautenberg Chemical Safety for the 21st Century Act
Are there any plans to create an article for the act that will replace the Toxic Substances Control Act of 1976? --Leyo 17:49, 25 July 2016 (UTC)
 * Its legislative history (including some opinions about it) are currently in Toxic Substances Control Act of 1976. Should be easy enough to write a stub for it from that main article. DMacks (talk) 17:56, 25 July 2016 (UTC)
 * Is the name stated above OK, i.e. not too long? I took it from the red link in Template:United States environmental law. --Leyo 20:37, 25 July 2016 (UTC)
 * Nobody? --Leyo 15:39, 10 October 2016 (UTC)

I created a stub. --Leyo 20:55, 14 November 2016 (UTC)

Fulvic acid at AFD
Please see Articles for deletion/Fulvic acid, about a class of organic chemicals. WhatamIdoing (talk) 18:28, 17 November 2016 (UTC)

Stub Expansion
Hello, recently I expanded the article Stöber process which was originally rated a stub class in quality. I believe it has been expanded significantly beyond a stub class, what is the proper way to get the article's quality re-rated on the projects quality scale? Thanks -- Imminent 77   (talk)  12:26, 18 November 2016 (UTC)
 * The article is certainly expanded, but the operative question is whether it was improved? Wikipedia is not a technical journal, it is an encyclopedia that provides overviews and introductions.  The venue does not aspire to compete with technical journals like Chemical Reviews or such, it operates at a far more general, almost cursory level. See WP:SECONDARY and WP:NOTJOURNAL.  --Smokefoot (talk) 13:20, 18 November 2016 (UTC)
 * I feel like the article has been improved, I expanded mostly on the sources that were already present in the article and added in the development on the two-step process. In addition to this there is not many secondary sources for the Stöber process, hence the reliance on the journals. This is my first major contribution to an article and I have nominated it for a peer review to try and improve it and get feedback. Would you have any recommendations for how the article could be improved? Also, with regards to my original question, how can someone get an article under the chemistry project reevaluated when it has been significantly changed, I can't find any information on that in the project. -- Imminent 77   (talk)  13:51, 18 November 2016 (UTC)
 * WikiProject Chemistry/Assessment would be the page for reassessment... if it were filled in with anything. Barring the use of that page, you can use the guidelines at Version 1.0 Editorial Team/Assessment. I have made some light edits here and there. It probably qualifies, at least, as a C-class article. --Izno (talk) 14:40, 18 November 2016 (UTC)
 * I flagged it as C. I agree with Smokefoot that it's too technical without non-technical content. That is, it's written almost entirely at a specialist/advanced level rather than being also/partially accessible to a wider audience. DMacks (talk) 14:46, 18 November 2016 (UTC)
 * Thank you for updating the class and thank you  for making some improvements to the article. It is a topic that I understand at an advanced level so it is hard to not write at that level. Thanks for the suggestions, I will look into adding some less technical content to make it more accessible to a wider audience. -- Imminent 77   (talk)  14:56, 18 November 2016 (UTC)
 * you see, I'm at a "advanced level". Right.  The goal is not to add less technical content, the goal is to remove overly technical content.  Jeesh.  --Smokefoot (talk) 16:46, 18 November 2016 (UTC)
 * But that is not WP:NOTJOURNAL's requirement. Its requirement is to make the introduction understandable to the lay-user. --Izno (talk) 16:52, 18 November 2016 (UTC)
 * Not sure why you are being so hostile, and I am not sure why you want to pass judgement on my understanding of the subject matter. I am just looking to contribute and get suggestions as to how to continue to improve the article. -- Imminent 77   (talk)  17:45, 18 November 2016 (UTC)

Aluminium triacetate
Hi, I'm from it.wiki and I recently edited this stub here on en.wiki, basically just for create the corresponding element on wikidata. I'm not used with the template:chembox here on en.wiki, so I'm leaving the work to you (lazy me...) before making any mistake. I'm reporting this here in the talk page 'cos I ignore what's the proper page where to signal new pages about chemistry. Thanks everybody --Samuele Madini (talk) 14:45, 14 November 2016 (UTC)
 * Thanks for starting the article. I have added the chembox template to the article, with some basic data.  -- Ed (Edgar181) 15:51, 14 November 2016 (UTC)
 * Would be surprising if it exists. Al(III) is v similar to Fe(III), and ferric triacetate is dubious.  Iron(III) acetate.--Smokefoot (talk) 18:41, 14 November 2016 (UTC)
 * I checked SciFinder briefly - 2000+ hits to something called aluminium acetate (Al(OAc)3). The current article, as it applies to description of composition and structure, is unsupported by any literature I can find. It's just "stuff' that people use, name, draw structures for, but have no bloody idea of what they have.  Lots of stuff like that is important, dont get me wrong. --Smokefoot (talk) 19:08, 14 November 2016 (UTC)
 * I ran into this problem some time ago and ended up rolling all the versions together at Aluminium acetate. I suspect that a lot of your hits may be coming from Burow's solution. I agree that the real structure is probably some sort of oxyacetate cluster, analogous to Basic beryllium acetate or Basic zinc acetate but I can't find any XRD data to back that up--Project Osprey (talk) 22:12, 14 November 2016 (UTC)
 * We already have the article Aluminium diacetate, which is overlapping Aluminium triacetate. If it is really all the same kind of substance then Aluminium acetate can be the real article, and not a pseudo-dab. Graeme Bartlett (talk) 22:30, 14 November 2016 (UTC)
 * Nice find. I am going to suggest that the tri- and diacetate articles be merged into Aluminium acetate. --Smokefoot (talk) 00:44, 15 November 2016 (UTC)

I have uploaded File:CaAl(OH)(H2O)Az2 dihydrate.png as the hypothesised structure formed when aluminium triacetate acts as a mordant with alizarin. The image looks poor, so if someone would re-draw it as an .SVG file, that would be excellent. Also, I have found that I could not tag it with the usual PD-chem template as it has been deleted. I have requested it be restored at Requests_for_undeletion and invite comment from anyone with a view on it being restored or remaining deleted. EdChem (talk) 01:41, 23 November 2016 (UTC)

New element names are approved
See This

Please move Ununtrium to Nihonium, Ununpentium to Moscovium, Ununseptium to Tennessine, and Ununoctium to Oganesson.--Abelium (talk) 08:53, 30 November 2016 (UTC)
 * Was done by Anthony Appleyard. Graeme Bartlett (talk) 12:04, 30 November 2016 (UTC)
 * There will be dozens of periodic tables to update as well. Graeme Bartlett (talk) 12:05, 30 November 2016 (UTC)

Big data improvement in Wikidata
Just to announce you than thanks to the work of, Wikidata increases its coverage of chemicals with a total of ~98'000 chemicals having an item. All data were imported from PubChem and ChEBI and respect the rules about sources leading to a high improvement of the data quality. Right now an important step has to start to curate the data especially to merge duplicated items. You are welcome to take part to this action and you can get in touch with the Chemistry project in WD for details.

From that work additional importations can start in order to add more identifiers but please announce your intention of data import before any huge importation in order to coordinate the work of bots and of contributors curating the conflicts. Snipre (talk) 10:10, 12 October 2016 (UTC)
 * Hi . Here at enwiki I am maintaining and  (in tandem). I am about to use Wikidata input big time (one development step at the time).
 * This work will require a mapping scheme for the data models (d:data model for compounds, en:data model implicitly in both es ), tracking categories, postponed issues, technical limits ( still is a wikitable...). I also expect questions like: "I am editor at enwiki. What and how to edit with this Wikidata thing?"
 * My question is: shall I flesh out a design setup with you/d:WP Chemistry first, or write a proposal + demo at Wikipedia talk:Chemical infobox right away?
 * My plan so far: start with CAS registry number; track in meaningful categories; category "data conflict between local input and wd input" will require the attention & edits; add parameter QID to overwrite natural QID expensively. Maybe allow multiple QID's in this early step, to cover articles with multiple compounds. When this is working, I'll transport (copy) it to . When it is stable (feedback is processed, articles/items being edited), we can expand to other identifiers (PubChem CID, ChEBI, ...). What do you think? -DePiep (talk) 08:39, 1 December 2016 (UTC)
 * Hello, . WD should not be a constraint for your organization system. So the best is to start with you proposal here in en:WP and later if your project agrees to use WD data we can start to map both data models. My advice is to clearly state how does en:WP want to deal with stereoisomers and for drug which compound is considered (the salt, the cation/anion or the neutral organic form). Snipre (talk) 09:57, 1 December 2016 (UTC)
 * No, WD not be not a constraint but be an asset! Well, I already have, and need to have, a data model for Chembox articles in mind (infobox Chem+Drug = 16.600 articles today). Expect 80% being straight single compound articles (en:articletitle = d:item). Lowest hanging fruit, use the default item.
 * Basically, I take WD as leading. Any intentional local overruling/overwriting should be sourced.
 * We might encounter:
 * Data issue A: local input conflicts with WD input ("parameter 1234-56-7 =/= WD P231 value 9876-54-3"). Some edit is needed. First try: correct the WD value over there, or correct (remove) local value. Second option: set "use QID=Q98765" (when articletitle =/= compoundname), or keep using local value. Third option: some structural improvement at WD (dunno. Split 'compound' item?).
 * Data issue B: multiple compounds in one page (eg Linalool; ~500 articles). Solution: allow indexed QID (compound-0 = default item, compound-1 = use QID=Q9876, compound-2 use QID=667788).
 * Data issue C: miscellaneous. Drugs that are a mab, virus or a combination (600 articles). These may not fit the 'chemical compound' definition. Must be solved differently (postponed).
 * -DePiep (talk) 10:27, 1 December 2016 (UTC)

Caltech
Another group are creating articles for Wikipedia seen at Wiki Ed/Caltech/Organic Geochemistry (Fall). Live pages include Crocetane Sponge biomarkers Okenane  Dinosterane 	and Epibrassicasterol. So far every article I have seen is OK in scope and quality. There is also a page 24-isopropyl cholestane coming up presently in User:Prestonkemeny/sandbox, and perhaps Bisnorhopanes from User:Cschou/sandbox. Graeme Bartlett (talk) 04:27, 3 December 2016 (UTC)

Nonsense edits from User:Drbogdan
The user User:Drbogdan add to all the element articles this: additional an interactive PSE table. This is absolutely unnecessary, because we have in all our element articles an interactive PSE-table:. What now? We have now two interactive tables. For me = nonsense. --Alchemist-hp (talk) 09:22, 3 December 2016 (UTC)


 * It is PeriodicTable-ImageMap. Interaction does not work in moboile view. Note: the compact periodic table Alchemist mentions is below in the navbox - and therefor does not show at all in mobile view. More on WT:ELEMENTS. -DePiep (talk) 10:52, 3 December 2016 (UTC)

Self-published book used as a source in Alcohol
Hi. Sorry to trouble the WikiProject over something so minor, but there's a self-published booked cited in Alcohol near the end of the section. It's written by Nicolae Sfetcu, who self-published his book through Lulu.com. Normally, I'd look for a better citation myself, but I'm terrible at chemistry, and I doubt I'd be competent to rewrite any part of the sourced content that was incorrect. If someone who knows what they're talking about could take a look (and hopefully replace the self-published book with something better), I'd really appreciate it. Thanks. NinjaRobotPirate (talk) 22:50, 6 December 2016 (UTC)

SMILES of trans-Bicalicene
c1c/c/2c\3/c(c3)c4/c(c/5\c(c2c1)c5)/ccc4 is a SMILES of trans-Bicalicene. But, Jmol can't recognize c1c/c/2c\3/c(c3)c4/c(c/5\c(c2c1)c5)/ccc4 as an aromatic molecule. --Abelium (talk) 16:03, 6 December 2016 (UTC)
 * If you have a SMILES string that Jmol does show right, you can overwrite using &lt;working-SMILES-string>. Do I understand that the second SMILES string in the trans-infobox is a different compound? Or is that the one to use for Jmol? -DePiep (talk) 16:14, 6 December 2016 (UTC)
 * The third-party web app doesn't illustrate aromatics differently than alternating single/double bonds (for example, benzene as ), so you may as well write a SMILES that puts the = where you want them to be displayed. But it does sound like a bug in Jmol that it doesn't even know to make your "c" have any semblance of sp2 (neither geometry nor pi bond). DMacks (talk) 16:55, 6 December 2016 (UTC)
 * One could charitably say "18π e– isn't aromatic, so it refuses to represent this structure as such":) But even if you shift the electrons to be zwitterionic and have discrete aromatic rings (see abstract image) Jmol can't figure out how to delocalize a charge even in simple cases. Both   and   fail badly for cyclopropenyl cation. DMacks (talk) 17:10, 6 December 2016 (UTC)


 * Again, what's when showing the second SMILES string already there? If OK, we can add Jmol legally. -DePiep (talk) 08:50, 7 December 2016 (UTC)

2016 Community Wishlist Survey Proposal to Revive Popular Pages
Greetings Members!

This is a one-time-only message to inform you about a technical proposal to revive your Popular Pages list in the 2016 Community Wishlist Survey that I think you may be interested in reviewing and perhaps even voting for:


 * Fix and improve Mr.Z-bot's popular pages report

If the above proposal gets in the Top 10 based on the votes, there is a high likelihood of this bot being restored so your project will again see monthly updates of popular pages.

Further, there are over 260 proposals in all to review and vote for, across many aspects of wikis.

Thank you for your consideration. Please note that voting for proposals continues through December 12, 2016.

Best regards, — Delivered: 17:56, 7 December 2016 (UTC)

Please help evaluate a draft at AFC
Please evaluate Draft:The Chemical Probes Portal for notability. If you don't wish to, or are not qualified to, do a full AFC review please post your comments to the Draft's Talk page. Thanks Roger (Dodger67) (talk) 09:13, 8 December 2016 (UTC)
 * ✅ After copyedit, accepted. Boghog (talk) 19:42, 9 December 2016 (UTC)

Hydroxyl group
Could some expert please look at the lead paragraph at Hydroxy group? It makes no sense. Details at Talk:Hydroxy group. Kendall-K1 (talk) 22:36, 14 December 2016 (UTC)
 * I didnt think that it was that bad. A common problem is that some introductions cram in a lot of adjectives and links and factoids. For example, the lede pushed the fact that O and H are bonded covalently, which is distracting and not a very important.--Smokefoot (talk) 00:17, 15 December 2016 (UTC)

Wikipedia talk:WikiProject Medicine
I have started a discussion at Wikipedia_talk:WikiProject_Medicine about two articles which may be of interest to members of this Wikiproject. ChemNerd (talk) 20:44, 19 December 2016 (UTC)

Essays for a class project
A number of new articles have shown up with chemistry-related themes. They appear to be essays written by students for a class project. My opinion is that many of the are very narrowly focused and not appropriate encyclopedia topics. Any thoughts about what to do with these? ChemNerd (talk) 20:28, 29 November 2016 (UTC)
 * Effects of cobalt from lithium ion batteries
 * Environmental Concerns of Headphone Disposal
 * Environmental effect of curl activator
 * Nitrate concentrations in the Mississippi River Basin
 * Secretion of Creosote Preservative into Aquatic Ecosystem
 * The environments future
 * Improper disposal of latex balloons and its environmental effects
 * Chemistry of Wetland Dredging


 * I think perhaps that the future of the environment article would require a crystal ball... almost all of them fail one sort of WP or another. According to the course page (Wiki Ed/FSW State College/ENC 1102 (Fall 2016)) these articles wont be needed after the 6th Dec. I say wait till then and quietly delete them afterwards. --Project Osprey (talk) 21:51, 29 November 2016 (UTC)
 * School articles don't get special treatment (one way or the other). Most of these seem like viable articles, if somewhat specialist in nature (but WP:N does not require something to be non-specialist). Probably the one article which must go regardless would be The environments future. I'd either prod or AFD that article quite quickly. --Izno (talk) 21:54, 29 November 2016 (UTC)
 * Not so much special treatment, more practicality. People who think their school grades might be effected by a deletion tend to fight it tooth and nail. Their are 24 students on this course, fighting through changes to most of those pages might take a lot of effort now, or very little in a week. --Project Osprey (talk) 22:08, 29 November 2016 (UTC)
 * Most of these probably deserve to be merged to parent articles under an "Environmental Effects" heading if the content is usable. shoy (reactions) 21:56, 29 November 2016 (UTC)
 * Some content could be merged, eg Environmental effect of curl activator merge to Stearalkonium chloride. Most of the topics sound too specialised and should therefore have content merged if it is any good and perhaps renamed if there is no broader or suitable topic yet. Also some content appears to original research, and so not suitable. Some other is WP:Undue suggesting problems, where this is none, or where the problem is grossly overstated. Graeme Bartlett (talk) 22:02, 29 November 2016 (UTC)
 * Secretion of creosote preservative into aquatic ecosystem can merge to creosote. Graeme Bartlett (talk) 23:20, 29 November 2016 (UTC)
 * A small part of Improper disposal of latex balloons and its environmental effects could be merged to Baloon. Graeme Bartlett (talk) 23:27, 29 November 2016 (UTC)
 * Effects of cobalt from lithium ion batteries overall could be original research, but the environmental effect part can be merged to Cobalt poisoning, other parts are already covered in Lithium-ion battery and Lithium cobalt oxide. Though perhaps Lithium cobalt oxide could take some additions too. Graeme Bartlett (talk) 23:43, 29 November 2016 (UTC)
 * Environmental concerns of headphone disposal has nothing worth merging as Polyvinyl chloride already covers the useful parts reasonably. Other content does not seem relevant. Graeme Bartlett (talk) 23:58, 29 November 2016 (UTC)
 * Chemistry of Wetland Dredging we could do with an article on geochemistry of wetlands, so by cutting the bit about dredging this might be usefully renamed. Graeme Bartlett (talk) 23:58, 29 November 2016 (UTC)
 * Nitrate concentrations in the Mississippi River Basin has nothing much worth merging anywhere else. Based on the references Nitrate in the Mississippi River Basin looks like a notable topic, but this article is almost all background material. Graeme Bartlett (talk) 23:58, 29 November 2016 (UTC)
 * Adsorbable organic halides looks OK as it is!! Graeme Bartlett (talk) 08:22, 30 November 2016 (UTC)


 * Comment: I came across some of these articles and then noticed some posts about them at User talk:Graeme Bartlett and User talk:Graeme Bartlett. While I think it's great that these students are using Wikipedia as part of their school projects, I also agree with that they should not really be given special treatment. Perhaps the part of the problem might be that some of the instructors of these students misunderstand what Wikipedia is about and have not done a good job explaining how it works? In addition, the fact that some of these kids are only concerned with getting a good grade than following relevant policies and guidelines sort of implies a not here approach that may be fine for them, but not really all that great for Wikipedia. I'm all for encouraging them and helping them out; however, if their grades depend upon anything they add to the mainspace, then they might be better off keeping their work as userspace drafts until their instructors can review their work. As experienced editors well know, anything added to the mainspace can be edited by anyone so there's no guarantee that what these students create will be what their instructors actually see. Moreover, some of the new talk pages of these articles seem to be being used more like a forum to post personal reviews of an article, which might be mistaken by some as granting some kind of ownership over article content to the article's creator. These are all things that would probably be OK with respect to a userspace draft, but are in my opinion asking for trouble in the mainspace. -- Marchjuly (talk) 04:48, 8 December 2016 (UTC)

FSW State College
On closer inspection these are coming from 2 different courses; one from FSW State College and the other from Louisiana State University.

The FSW State College has a course page (Wiki Ed/FSW State College/ENC 1102 (Fall 2016)) and is run by User:Norobello, most of the pages coming out of it don't apply to us but it might to woth flagging them to someone. Here's an overview of the students activities.


 * There is a discussion of another article related to the FSW State course at Talk:Issues of the Evolution v.s. Creation Debate (added above), and I have pinged the Wikipedia course ambassador, , because I think the goals of the course on critical thinking through argumentation are not necessarily consistent with producing a neutral article. In the creation / evolution case, the result is a content fork that is a debate (and we have a template on this specific topic).  The article's author uses a "compare/contrast approach in comparing either side of the debate" which risks WP:FALSEBALANCE, which could be a problem when salvaging content from articles which are not kept.  Ian, can WikiProjects that are likely to be affected by courses like this get a notification much earlier in the course?  This situation would have been less problematic if there had been an early intervention to point out unsuitable topics and duplication.  EdChem (talk) 21:31, 3 December 2016 (UTC)

Louisiana State University
The second is part of a Louisiana State University, Baton Rouge, LA. There is no course page and I can't identify any user in charge which is frustrating as the pages do apply to us. I've only been able to identify 12 students, there may well be more, here's an overview of their activities. I hope you don't mind but I've copied your comments in.

Can you help with this case of LSU? I think you're the right person to let know about an 'unofficial' program since you're listed as the outreach person at m:Wiki Education Foundation. --Izno (talk) 13:57, 30 November 2016 (UTC)
 * My colleague User:Helaine (Wiki Ed) has reached out to the instructor. Early in the term we made a few attempts to reach out the instructor to offer our support, to no avail. Hopefully this time we succeed as we'd like to provide our resources if possible! Thanks for the heads up, - Samantha (Wiki Ed) (talk) 23:34, 30 November 2016 (UTC)


 * I am adding more comments Graeme Bartlett (talk) 05:27, 3 December 2016 (UTC)

Others that may be part of the same course:

Discussion of what happened
A discussion has been started at Education noticeboard/Archive 16 which includes at least one of the courses mentioned above. Input and thoughts from all welcome. EdChem (talk) 08:10, 9 December 2016 (UTC)
 * OK it is now time to clean up the results. Graeme Bartlett (talk) 11:48, 6 January 2017 (UTC)

Missing topics list
My list of missing topics about chemistry and related subjects is updated - Skysmith (talk) 13:20, 8 January 2017 (UTC)

Little help please?
Hi chemists. I'm slowly going through checking old articles that were translated from foreign languages and I've come across McIlvaine buffer. Please could someone with relevant expertise review it and give their opinion? Thanks and all the best— S Marshall T/C 21:48, 5 January 2017 (UTC)
 * This article is largely redundant as the reference is cited and a selection of values is shown in a table at buffer solution. I suggest speedy deletion. Petergans (talk) 13:38, 20 January 2017 (UTC)

WikiJournal of Science promotion
T.Shafee(Evo &#38; Evo)talk 10:39, 24 January 2017 (UTC)

Hydrotennessic acid
Hey everybody, I am proposing a new article on an acid based on the recently discovered element, Tennessine. I wrote an article a few months ago on it called hydrotennessic acid, but it was deleted. I was wondering if anyone would be willing to write an article on it. — Preceding unsigned comment added by Larenmclane (talk • contribs) 02:04, 29 January 2017 (UTC)
 * Why would any reader be interested in hydrotennessic acid? I think that is the first question to ask before writing such an article.  See WP:NOTABILITY. --Smokefoot (talk) 03:10, 29 January 2017 (UTC)
 * Not to mention the fact that given that Ts is expected to be a metal, it would surely dissociate as H−Ts+ instead of H+Ts− (with Ts having lower electronegativity than H) – and that's assuming you could actually get enough to experiment on, which you can't? Double sharp (talk) 06:09, 29 January 2017 (UTC)
 * Also worth remembering is that most of the chemical information at tennessine is predictions and expectations and even assuming you could make HTs(aq), the half-life is so short that you wouldn't have it for long enough to really study, so it is doubtful that such an article could say much... in fact, having a WP:RS-compliant source attesting to its existence would be appropriate before considering starting an article. EdChem (talk) 06:18, 29 January 2017 (UTC)
 * I proposed this for deletion before because it was entirely original research. The highlight, quoting the article "With current technology, Hydrotennessic Acid is extremely difficult to make." Because it was a prod, you can contest it and have it restored. However an article should be based on previous publications, and not on calculations and predictions of a Wikipedian. Graeme Bartlett (talk) 11:07, 29 January 2017 (UTC)
 * There are a few published predictions about the TsH molecule (one two), but nothing about what bulk TsH (aq) would be like. Double sharp (talk) 14:16, 29 January 2017 (UTC)
 * Given the short half-life of elements such as this, it is highly unlikely that enough material could be synthesized to enable a measurement to be undertaken. A purely theoretical value has no place in any article other than one dealing with predictions, where the basis of the prediction can be laid out. Petergans (talk) 14:42, 29 January 2017 (UTC)

Looking for comparison method for dataset matching
I am looking for a method to compare datasets from different origins and to define if the datasets are about the same topic. I provide an example in the table below:

From the example above we can define with a high confidence that Dataset from DB1 and Dataset from DB3 are the same and can be linked together. For Dataset from DB2 we have a medium confidence compared to Dataset from DB1 and for Dataset from DB4 a low confidence. Snipre (talk) 11:11, 27 January 2017 (UTC)
 * One can start with Regression analysis, and ask WP:MATH people? -DePiep (talk) 18:59, 29 January 2017 (UTC)

Incorrect formulas and symbols on basic chemistry pages
As a high school chemistry teacher, I know many students jump to Wikipedia for answers and examples of various concepts. I took a look at the single replacement reaction page, and noticed many errors. Formulas such as ZnCl (Zn has a +2 charge, not a +1), hydrogen written as H, not H2, down arrows on gases evoloved like hydrogen (which is used to denote precipitates, whereas up arrows denote gases produced), and erroneous reactions such as Na + BrCl3 --> NaCl + Br. I am well aware that this is volunteer driven to correct and update the pages, so I will do my best to correct errors as I find them (hoping editing subscripts and superscripts are intuitive). I would ask others to make a concerted effort to look at the basic chemistry pages to make sure that material is correct since so many students use them as a go to source for information.108.217.142.106 (talk) 04:21, 3 February 2017 (UTC)
 * Could you give the name of that article? -DePiep (talk) 08:43, 3 February 2017 (UTC)
 * single displacement reaction. -- Daniel Mietchen (talk) 08:58, 3 February 2017 (UTC)
 * Of course, how could I miss that. ;-) -DePiep (talk) 09:35, 3 February 2017 (UTC)


 * Reply: yes, that is how improvements happen on Wikipedia, but the 'concerted' part is a more difficult route. This idea: knowing how Wikipedia works, why not stimulate your students in improving WP? Like, rewarding them (1) for finding errors, (2) edit-improve them, and (3) advise them to go into chemistry? Sure that would be a good chemistry student :-). -DePiep (talk) 09:35, 3 February 2017 (UTC)

Comment on wikidata transclusion from the User:ProteinBoxBot team
I just realized that I posted this message over on WT:CHEMS, when probably it would have been better here. Apologies for cross posting, but just want to be sure the right people see it. For continuity, I suggest any followup discussion be continued there... Cheers, Andrew Su (talk) 00:43, 26 January 2017 (UTC)

I updated our analysis/comparison of Wikidata and Wikipedia PubChem CID}. Sebotic (talk) 01:36, 7 February 2017 (UTC)

Re-write of Jahn-Teller effect
Several members of the International Steering Committee of the Symposia on the Jahn-Teller effect have made large edits to (surprise!) Jahn-Teller effect. The additions are well written and well referenced but expansive and highly technical. So technical in fact that the effects that I've always associated with JT-effect like high-spin low-spin distortions simply aren't discussed. These changes were also made as one massive edit (+43,242)‎. It would seem a shame to remove expert understanding from the article but I think we may need to reinstate parts of the original page to make it more accessible... maybe under some sort of 'overview' heading? There is a discussion at the talk page. --Project Osprey (talk) 23:02, 16 December 2016 (UTC)
 * One approach - some might think too drastic - is to revert their entire edit. And ask/demand/cajole them to make changes incrementally, lower the technical level (its impossible now), and - get this -- actually explain or justify their edits. I will do this and wait to see if and how they respond.  If they dont, then some of us bring in the parts that are intelligible. If fellow editors think that I am being rash, then re-revert.  No hurt feelings.--Smokefoot (talk) 23:38, 16 December 2016 (UTC)
 * I think it's safe to assume good faith in all this. The re-write was done as a draft (Draft:Jahn-Teller effect), it's transclusion as one massive edit seems to be due to a procedural error - they wrote the draft and submitted for review, but were told that as the topic already exists they should edit there directly, so they did. Incremental changes can be seen at the Draft history, although there are no edit summaries; work started in September. Considering the effort that must have gone into it I imagine they'll want a positive outcome. --Project Osprey (talk) 00:39, 17 December 2016 (UTC)
 * Absolutely I assume good faith. But one can act with good faith and still do something ill-advisedly.  My thinking is that we current editors have little ability for making the article better, and just maybe we'll get them to do it as the price to rescue their work.  The downside is that, what, 4-6 people in the world who want to know the intracacies of the J-T effect in the next few weeks will be inconvenienced. It is also instructive to look at the German version.--Smokefoot (talk) 04:18, 17 December 2016 (UTC)
 * ,, I propose the content introduced by Janette Dunn at Nottingham be moved into a Talk entry (using collapsed markup), and that the issues of its sourcing, its gradual introduction, and its level of expertise and language be addressed from there. It is great material, and certain to improve the article in the long run (as it is expert both in scope and detail). But it would be a serious error, in my opinion, to begin to allow large blocks of unsourced material, even from experts, as I have stated to Janette, and to Smoke, at their respective Talk pages. Moving it to a collapsed section in Talk and leaving the earlier article will restore a stable, if marginally expert and marginally sourced article. But it will allow moves of material from the Talk archive as source, into the article main space, a section at a time, where we can, over time, ensure sourcing and proper level of newly introduced material. This accomplishes all purposes—use of the expert material, improvement of the article, submission to WP guidelines, etc.—with minimal work. Meanwhile, I am going to engage JD offline, and ask if a couple of their students can be assigned to provide good secondary sources for the material already posted. Cheers. Le PRof Leprof 7272 (talk) 04:47, 22 February 2017 (UTC)

Pyrithione
I recently wrote an article on pyrithione which exists as a pair of tautomers (at right). Based on this source published by the University of Barcelona, I put pKa values of "&minus;1.95 and +4.6 (thiol proton)" in the article. I can find sources supporting the 4.6 value, but not for the &minus;1.95 value. has challenged it on the article talk page, but he cannot access the book source on google (I can view it from Australia, so access depends on the location of your IP address). The reference the book provides supporting the claim is no. 40, which should appear on page 356, here, but I cannot see that page to look to the source's source. My initial interpretation was the two values are for the two tautomers, as it seems reasonable to me that the thiol tautomer would be a weaker acid than the thione, and the greater ionisation of the thione would account for it being the major tautomeric form (despite the aromaticity of the thiol). However, the difference in values is very large and Petergans is correct that &minus;1.95 is into the strong acid range. Can anyone explain why there are two values, as the quoted source suggests? Alternatively, should we remove the second value and just list +4.6. If so, should we make some note / comment about it? Thanks to all. :) EdChem (talk) 00:23, 19 January 2017 (UTC)
 * I can't access the book. Scifinder has no pka info for the thione form but gives 4.49 for the thiol with this source . The page states that the thione form dominates, that's a big surprise to me (surely aromaticity always beats cross-congregation?) but the ref is for the solid state and that's its own weird area, any idea if that holds true in solution? --Project Osprey (talk) 10:03, 19 January 2017 (UTC)


 * Ref 40 is "". This indeed supports 2 values (-1.95 and 4.67; both averages of 6 independent values, both sigma of 0.03).  If I read it correctly, the -1.95 is measured at high dilution (0.5 . 10^-4 M) using sulfuric acid or phosphate buffers with a spectroscopic method, the second is a potentiometrically determined value at high concentration (239 . 10^-4 M).  Please have a proper look at the reference before using it, the interpretations of these pKa measurements are outside of my confidence zone.  --Dirk Beetstra T  C 10:57, 19 January 2017 (UTC)
 * I have seen the page where a pK value of -1.95 is cited, though it is described as pK1 rather than pKa. A value of pKa of -1.95 is to be associated with a rather strong acid. Does the protonated form of the compound [C5H4N(OH)(SH)]+ form at pH 0 and less? Petergans (talk) 11:57, 19 January 2017 (UTC)
 * This is an area where I have some experimental and theoretical expertise. Call on me somehow, if you cannot settle on a good course here. Cheers. Le Prof Leprof 7272 (talk) 04:54, 22 February 2017 (UTC)

new article "Glaring Chemical Errors Persist for Years on Wikipedia"
I just got alerted by @WikiResearch about a paper looking into the quality of chemistry on Wikipedia (http://pubs.acs.org/doi/abs/10.1021/acs.jchemed.6b00478). I don't have access to the paper yet, emailed the author, and am looking forward to reading it. --Egon Willighagen (talk) 08:50, 1 February 2017 (UTC)
 * It gives 3 examples, all structural errors in images. The author did correct the errors he found; however despite encouraging more people to edit in the paper he hasn't returned since making those 3 fixes in September. Bit of a cheap shot really. --Project Osprey (talk) 10:59, 1 February 2017 (UTC)
 * It's not just that he didn't keep up his good work after fixing these three articles on en.wp. His fix was to redraw the images and replace them in the articles on en.wp. Good! But in the JChemEd article, he also noted that one of the images was tagged on commons as having a mistake. He didn't even tag the other ones likewise, leaving those images themselves (and the other WP sites that use them) just as likely to misinform readers as before. Can't fault someone for not doing volunteer work, but it's a weak position to leave a problem present that you know how to fix (or at least alert others to fix) and then loudly complain that there are problems that someone should fix. For the record, I fixed two of the images on commons. This set of changes I don't have time to work on right now. DMacks (talk) 16:04, 1 February 2017 (UTC)
 * The issue with Tryptamine I'll except, but the others are pretty obscure examples. The Pfitzner–Moffatt oxidation is defunct in favor of the Swern oxidation) and Novobiocin was taken off the market some years back (image issue is from after that time).--Project Osprey (talk) 17:11, 1 February 2017 (UTC)
 * The problem is not that mistakes persist for many years but that it takes many years before someone notices the error. I can give several examples where the peer review took between 7 and 10 years. Latest instance for example here: https://en.wikipedia.org/wiki/Talk:Directed_ortho_metalation (11 years). We simply need more reviewers. V8rik (talk) 17:49, 1 February 2017 (UTC)
 * V8rik is exactly right. Many of us do more editing in a week than Mandern expended in a lifetime on Wikipedia, and we dont try to get some %$*ing publication for our efforts.  Now that I have that off my chest, I will point out that I see many high level chemists consulting Wikipedia all the time.  And increasingly images from Wikipedia are creeping into lectures, sometimes even with attribution.--Smokefoot (talk) 20:46, 1 February 2017 (UTC)
 * From the abstract: "Even when these mistakes are discovered and reported, articles are sometimes subsequently left uncorrected."
 * This goes without saying, though? We're all volunteers here. I fixed images here and there, and it often took hours. You check the reference of the image, you redraw the image (and often make it clearer for undergraduates, also with colors), you upload it, you put some explanation, etc.
 * It's sad that Michael Mandler looked for a shortcut to his 15 minutes of fame by belittling a community he knows nothing about. In Donald Trump's style of tweet: VERY SAD!
 * Georginho (talk) 21:13, 1 February 2017 (UTC)
 * Thank you (seriously) for your critical comments on this page. I only recently got into Wikipedia editing and I have tremendous respect for you all. I'm not great at Wikipedia software, but I will continue to make edits on chemistry articles as soon as I find them. I agree wholeheartedly with Georginho; fixing images takes hours. If you have Chemdraw, obviously this task is much easier, but I assume most people may not have this software. However, I do want to point out to Georginho that I did not mean to belittle the Wikipedia community at ALL.Mandlerm (talk) 16:58, 5 February 2017 (UTC)
 * I see you did not cite a source for the "upset guy" who is looking at the Pfitzner–Moffatt oxidation mistake in the abstract-image. Did you draw it yourself? DMacks (talk) 16:23, 14 February 2017 (UTC)

Please look at the section "Wiki Howlers" on my personal page. Petergans (talk) 10:30, 2 February 2017 (UTC)
 * Some good news. Over at WT:CHEMICALS there is an extensive discussion about data quality wrt exteranal databases (like PubChem DB). Over at Wikidata, smart bot operators have imported 170k(!) PubChem CID identifiers, names, and their properties. A task at hand now is to check the PubChem CID with the enwiki value (in ~17k, ). Now it appears that a serious number of PubChem database values are incorrect. We cannot blindly import the PubChem data into our infoboxes (from Wikidata). So there are errors in external database(s) too (for years?). The good news is that Wikipedians are mass-analysing that data to improve the quality. It's good for PubChem too. -DePiep (talk) 09:06, 3 February 2017 (UTC)
 * That talk is here, and actually is a fork/continuation of here ;-).
 * That is welcome news. Perhaps we should write a rebuttal? --Project Osprey (talk) 10:32, 3 February 2017 (UTC)
 * A rebuttal when there has been delivered? (could be 202x). I have no rub with Mandlerm or their publication. These opinions and judgements about WP happen often, and their core is not faulty. I'd say let's keep working on individual articles, and general setups like WD and infoboxes. JChemEd does have other WIkipedia publications too, I hope. -DePiep (talk) 11:12, 3 February 2017 (UTC)
 * Now having read the paper, and seeing the comments here, maybe it's good to balance this paper with this one, which shows how great work WikiProject Chemistry has done! https://jcheminf.springeropen.com/articles/10.1186/s13321-015-0061-y — Preceding unsigned comment added by Egon Willighagen (talk • contribs) 08:22, 5 February 2017 (UTC)
 * Thanks for pointing to this article! Very uplifting and energizing. V8rik (talk) 20:57, 5 February 2017 (UTC)
 * Thanks for pointing to this article! -DePiep (talk) 23:43, 5 February 2017 (UTC)
 * The paper is 2 years old. Are there any tasks left to improve Wikipedia chemicals? Or is this a welcome check/approval on the quality of SMILES in enwiki? -DePiep (talk) 14:38, 6 February 2017 (UTC)
 * Following up, I should mention that we had this article in J Chem Ed at the end of 2016, which aims to encourage responsible editing of chemistry on Wikipedia. Walkerma (talk) 03:43, 13 February 2017 (UTC)
 * ...which the article we're discussing cited, for the idea of reader-visible content validation in the chemboxes. DMacks (talk) 16:26, 14 February 2017 (UTC)
 * My advice, don't shoot the messenger, and be thankful that he did not contact anyone more seasoned at WP to provide observations to support his article. Any one of us, certainly, could share tens if not hundreds of further known issues within chemistry articles, where accurate representation via images is a clear leading area (because try as we might, we all all do not have ample time, every time we come upon an issue, to address it thoroughly, by going offline, and creating new, corrected images). But other areas of article shortcomings are just as real, the most egregious in my view being the non-authoritative scope of many articles, i.e., their not covering things they should, and covering things they need not (along with the article structural issues that follow from such omissions and insertions). No, I think this JCE writer does us a service, and I wish more academics would take even the time that he did. Truth is—and this is Le Prof the academic, speaking, now, and not Le Prof the editor—no organic chemist worth his salt would send anyone to WP to get their start on a subject. (With Clayden, Greeves & Warren available, why would we?) The material is simply not worth the time it takes for a supervising tutor or instructor to correct or fill in the inadequacies that exist in WP materials. (I say so just about this, in one of my principle areas of expertise.) And in the end, it does not matter why errors persist—with time to discover, lack of expert feedback, WP momentum, politics sometimes embroiling change, difficulty of accessing better images or authoritative resources, lack of expert editors to make the changes, etc.—it is simply true that substantive errors in scope and detail persist. Respect you all, Smoke, V8rik, Dmacks, Osprey. But this is my opinion. Cheers. Le Prof Leprof 7272 (talk) 05:04, 22 February 2017 (UTC)

Hoax at Henderson–Hasselbalch equation
There's been a long-running hoax at Henderson–Hasselbalch equation, see Talk:Henderson–Hasselbalch equation for an explanation. I've removed a false name for an equation and protected the page, but I think the rest of the content and maths needs properly verifying. Fences &amp;  Windows  20:30, 15 February 2017 (UTC)
 * thanks for bringing this to our attention. I was surprised to see the removal of the textbook by Zumdahl, though, it has long been used at tertiary levels and is reliable, as I understand it.  EdChem (talk) 12:06, 19 February 2017 (UTC)
 * EdChem, if there's a genuine textbook by Zumdahl it's not published by Content Technologies Inc. I found that "edition" on Google Books and without doubt it copies Wikipedia. See WP:PUS for more such books. CTI appears to lift ISBNs and author names to pretend to be presenting real textbooks. Fences  &amp;  Windows  07:10, 20 February 2017 (UTC)
 * , you are right that that link is clearly a copy of Wikipedia. Here is a link to the 9th edition to the actual textbook by Zumdahl and Zumdahl published by Cengage, and there is no if as to whether it is a well-established and genuine textbook.  I wasn't aware of this form of fakery, though, and it is annoying, wasting editors' time and I don't see the benefit to CTI of sticking such references into WP articles.  :(  EdChem (talk) 07:52, 20 February 2017 (UTC)
 * EdChem, my wording a bit throwaway, I didn't doubt there's a real textbook. Does it contain anything about the "Heylman equation"? I very much doubt it. CTI operate by selling "revision guides" and "textbook guides", capitalising on students who can't afford the real textbooks I assume. These references being used in Wikipedia is an unfortunate side effect - they're added by well-meaning but unwary Wikipedians, not CTI employees. Fences  &amp;  Windows  08:47, 20 February 2017 (UTC)
 * , I don't have a copy of Zumdahl to hand, but I have taught the H-H equation plenty of times and I don't recall hearing of the Heylman equation, nor do I see it in the couple of texts I checked. All the online sources I can find, including at Google Books, track back to copies of the WP article or to CTI, so I am very comfortable with your removal of the name.  Thanks for explaining that the damage to WP content is from well-meaning Wikipedians rather than CTI, but the CTI profiteering on WP content does irk me.  EdChem (talk) 12:28, 21 February 2017 (UTC)
 * Leaving Steve's book citation to others to sort, as expressed to F&W at the article Talk page, Mssrs Heylman and Lardinois are clearly two students at Wisconsin, with a reverting edit from IP clearly tracing there (and the students names both appearing in a 2016 commencement announcement). Relatively clear since this is not a case of a Smith-Jones. Bottom line, thanks for the persistent correction, and I'll send an email to these two to tell them to knock it off. Cheers. Le Prof Leprof 7272 (talk) 05:44, 22 February 2017 (UTC)