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This is an old revision of this page, as edited by Sebotic (talk | contribs) at 01:36, 7 February 2017 (→‎Comment on wikidata transclusion from the User:ProteinBoxBot team). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

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Discussion of the WikiProject Chemistry - Please add your comment and discussion here. Older discussions are archived.

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This discussion page is about the Chemistry project itself, for detailed, in-depth discussions about specific topics, you'd be best served at the talk page of the specific subject, e.g., Chemicals, Chemical infoboxes, etc. There is also an image request page which might be of interest to you.

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)[reply]

Its legislative history (including some opinions about it) are currently in Toxic Substances Control Act of 1976#2015. Should be easy enough to write a stub for it from that main article. DMacks (talk) 17:56, 25 July 2016 (UTC)[reply]
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)[reply]
Nobody? --Leyo 15:39, 10 October 2016 (UTC)[reply]

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

Big data improvement in Wikidata

Just to announce you than thanks to the work of @Sebotic:, 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)[reply]

Hi Snipre. Here at enwiki I am maintaining {{Chembox}} and {{Drugbox}} (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 {{Chem&Drug infobox}}es), tracking categories, postponed issues, technical limits ({{Chembox}} 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 {{Drugbox}}. 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)[reply]
Hello, DePiep. 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)[reply]
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 |CASNo=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)[reply]

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)[reply]

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)[reply]
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)[reply]
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)[reply]
I ran into this problem some time ago and ended up rolling all the versions together at Aluminium acetate. @Smokefoot: 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)[reply]
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)[reply]
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)[reply]

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 Wikipedia:Requests_for_undeletion#Template:PD-chem and invite comment from anyone with a view on it being restored or remaining deleted. EdChem (talk) 01:41, 23 November 2016 (UTC)[reply]

Fulvic acid at AFD

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

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 --Imminent77 (talk) 12:26, 18 November 2016 (UTC)[reply]

The article is certainly expanded, but the operative question is whether it was improved? Imminent77Wikipedia 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)[reply]
@Smokefoot: 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. --Imminent77 (talk) 13:51, 18 November 2016 (UTC)[reply]
Wikipedia: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 Wikipedia: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)[reply]
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)[reply]
Thank you DMacks for updating the class and thank you Izno 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. --Imminent77 (talk) 14:56, 18 November 2016 (UTC)[reply]
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)[reply]
But that is not WP:NOTJOURNAL's requirement. Its requirement is to make at least the introduction understandable to the lay-user. --Izno (talk) 16:52, 18 November 2016 (UTC)[reply]
Not sure why you are being so hostile Smokefoot, 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. --Imminent77 (talk) 17:45, 18 November 2016 (UTC)[reply]

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)[reply]

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 (Wikipedia: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)[reply]
@Project Osprey: 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)[reply]
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)[reply]
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)[reply]
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)[reply]
Secretion of creosote preservative into aquatic ecosystem can merge to creosote. Graeme Bartlett (talk) 23:20, 29 November 2016 (UTC)[reply]
A small part of Improper disposal of latex balloons and its environmental effects could be merged to Baloon#Safety and environmental concerns. Graeme Bartlett (talk) 23:27, 29 November 2016 (UTC)[reply]
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)[reply]
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)[reply]
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)[reply]
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)[reply]
Adsorbable organic halides looks OK as it is!! Graeme Bartlett (talk) 08:22, 30 November 2016 (UTC)[reply]
  • Comment: I came across some of these articles and then noticed some posts about them at User talk:Graeme Bartlett#Hello and User talk:Graeme Bartlett#Non-free images. While I think it's great that these students are using Wikipedia as part of their school projects, I also agree with Izno 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)[reply]

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 (Wikipedia: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.

Article Editor Comment
Florida Amendment 2 (2016) User:Tkratzer Editor is adding to this pre-existing page, no obvious issues
N/A User:Abarber2 No significant edits as of yet
N/A User:Amclure No significant edits as of yet
The Impact of Cannabis in Colorado User:Egarcia36 New article
I straight-redirected to cannabis in Colorado. The professor-student pair can sort this out. --Izno (talk) 13:36, 30 November 2016 (UTC)[reply]
Deaf culture User:Kira2525 Editor is adding to this pre-existing page
The environments future User:Jsotelo3 New article. Fails WP:Crystalball
I've AFDed. Review at WP:Articles for deletion/The environments future. --Izno (talk) 13:39, 30 November 2016 (UTC)[reply]
Smoking Cigarettes User:Tklisby Already merged into Tobacco smoking under an WP:A10 (also major edits to Major religious groups )
Causes of Breast Cancer User:Caitlinsmitt Already merged into Risk factors for breast cancer under an WP:A10, however this page already has MEDRS issues
Psychiatric and Mental Health Nursing in the United States Army User:Abarber2 Large additions made to this pre-existing page, no evidence of copy editing by others.
N/A User:Gainesd2112 No significant edits as of yet
Women's rights in North Korea User:Mahmed1 New article but a valid one, has already attracted other editors
Agreed, looks good. --Izno (talk) 13:53, 30 November 2016 (UTC)[reply]
Technology Changes in Music Media User:Ngibb New article, not yet copyedited
Nominated for a merge with Timeline of audio formats. --Izno (talk) 13:53, 30 November 2016 (UTC)[reply]
N/A User:BARONBOGLE97 No new pages yet but has 'The Impact of Oil Drilling in Texas' in sandbox
N/A User:Chsleggett10 No new pages yet but has a sandboxed page on basketball player LeBron Raymone James
N/A User:Smanis No new pages yet but has a sandboxed page on Confucianism
Issues of the Evolution v.s. Creation Debate User:Gabriel Gonzalez19 Article has an ongoing merge discussion as a content fork of creation–evolution controversy
N/A User:Jsouden No significant edits as of yet
N/A User:Dlutz1 No new pages yet but has a sandboxed page on 'American Workplace Discrimination Continues To Be Prevalent In The Twenty-First Century'
N/A User:Chelseaw No new pages yet but has a sandboxed page on 'How a Tanning Bed Works'
Lecanorchis tabugawaensis User:HCCCJOHNKE New page. Needs polishing but is ok overall
N/A User:Ecampos81 Edits to Special education in the United States and a sandboxed article of bullying
  • 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, Ian (Wiki Ed), 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)[reply]

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. @Graeme Bartlett: I hope you don't mind but I've copied your comments in.

Page Editor Comment Result
N/A User:Acurra1 Large sandboxes article of pollution in the Danube AFC declined, editor has merged nothing as all content exists in other articles already
Draft:Meth Lab Waste Disposal User:Ashlynmcc I declined this at WP:AFC, and suggested a merge to clandestine chemistry
Effects of cobalt from lithium ion batteries User:Mbinns2 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. Wikipedia:Articles for deletion/Effects of cobalt from lithium ion batteries
Environmental concerns of headphone disposal User:Zzheng5 Has nothing worth merging as Polyvinyl chloride already covers the useful parts reasonably. Other content does not seem relevant. PROD
Environmental effect of curl activator User:KJenkin94 merge to Stearalkonium chloride? merged to Benzalkonium chloride#Degradation
Nitrate concentrations in the Mississippi River Basin User:Holivi5 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. moved to Nitrate in the Mississippi River Basin
Improper disposal of latex balloons and its environmental effects User:Jgrennel Elements could be merged to Baloon#Safety and environmental concerns. merged to Balloon#Safety and environmental concerns
Chemistry of wetland dredging User:Mleb111 we could do with an article on geochemistry of wetlands, so by cutting the bit about dredging this might be usefully renamed. leaving this as tpoic is stand alone enough
Urine patches in cattle pastures User:Abutte2 suggest renaming to Urine patches to make this a broader topic, as there is no good topic to merge to. Renamed to Cattle urine patches, as the main topic of writing on urine patch seems to be pet damage to lawns.
Secretion of creosote preservative into aquatic ecosystem ‎ User:Michael.p.hayes can merge to creosote. merged to Creosote#Release into environment
Adsorbable organic halides User:Ashweyron Ok! New article
Draft:Oilfield scale inhibition User:Eampiah Draft-space article AFC accepted as Oilfield scale inhibition
Environmental impacts of sterile food packaging User:LSUENCHEM16
UV filters User:Gabdal1 needs to be merged with UV filter, author and I are communicating. User ultimately updated UV filter and UV filters is a redirect.

@Samantha (Wiki Ed): 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)[reply]

@Izno: 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)[reply]
I am adding more comments Graeme Bartlett (talk) 05:27, 3 December 2016 (UTC)[reply]

Others that may be part of the same course:

Page Editor Comment Result
Disposal of CDs and DVDs - Environmental Impact User:Remilawal suggest merging to Polycarbonate merged to Polycarbonate#Environmental impact
Microwave Popcorn Bag User:Cdong7 is mostly about perfluorinated compounds in the environment Wikipedia:Articles for deletion/Microwave Popcorn Bag closed as merge to Microwave popcorn#Safety issue
Nail Polish Remover's Impact on Environment User:Melissaplam suggest that a tiny amount could be merged to acetone#Environmental effects Wikipedia:Articles for deletion/Environmental impact of nail polish remover closed as merge to Environmental impact of pharmaceuticals and personal care products.
User:Nfalgo3/sandbox User:Nfalgo3 plans to edit bagasse AFC submission was declined, and user did not proceed with a merge as suggested.
Environmental impact of menstrual cups User:ValérieR some diagrams like File:Degradation Si.png may be worth merging to topic of silicone See Wikipedia:Articles for deletion/Environmental impact of menstrual cups

Discussion of what happened

A discussion has been started at Wikipedia:Education noticeboard/Archive 16#Articles being created as class projects which includes at least one of the courses mentioned above. Input and thoughts from all welcome. EdChem (talk) 08:10, 9 December 2016 (UTC)[reply]

OK it is now time to clean up the results. Graeme Bartlett (talk) 11:48, 6 January 2017 (UTC)[reply]

Caltech

Another group are creating articles for Wikipedia seen at Wikipedia: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)[reply]

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)[reply]

Was done by Anthony Appleyard. Graeme Bartlett (talk) 12:04, 30 November 2016 (UTC)[reply]
There will be dozens of periodic tables to update as well. Graeme Bartlett (talk) 12:05, 30 November 2016 (UTC)[reply]

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: {{compact periodic table}}. What now? We have now two interactive tables. For me = nonsense. --Alchemist-hp (talk) 09:22, 3 December 2016 (UTC)[reply]

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)[reply]

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.[1] --Abelium (talk) 16:03, 6 December 2016 (UTC)[reply]

If you have a SMILES string that Jmol does show right, you can overwrite using |Jmol=<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)[reply]
The third-party web app doesn't illustrate aromatics differently than alternating single/double bonds (for example, benzene as c1ccccc1), 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)[reply]
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 doi:10.1039/C2CP43426A abstract image) Jmol can't figure out how to delocalize a charge even in simple cases. Both c1cc1 and c1[c+]c1 fail badly for cyclopropenyl cation. DMacks (talk) 17:10, 6 December 2016 (UTC)[reply]

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#Physical and chemical properties 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)[reply]

Greetings WikiProject Chemistry 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:

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, Stevietheman — Delivered: 17:56, 7 December 2016 (UTC)[reply]

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)[reply]

 Done After copyedit, accepted. Boghog (talk) 19:42, 9 December 2016 (UTC)[reply]

Hydroxyl group

Could some expert please look at the lead paragraph at Hydroxy group? It makes no sense. Details at Talk:Hydroxy group#What a horrible article. Kendall-K1 (talk) 22:36, 14 December 2016 (UTC)[reply]

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)[reply]

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)[reply]

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)[reply]
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)[reply]
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)[reply]

Wikipedia talk:WikiProject Medicine#Acadesine and AICA ribonucleotide

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

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)[reply]

This article is largely redundant as the reference is cited and a selection of values is shown in a table at buffer solution#"Universal" buffer mixtures. I suggest speedy deletion. Petergans (talk) 13:38, 20 January 2017 (UTC)[reply]

Missing topics list

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

Pyrithione

Pyrithione tautomerisation

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 "−1.95 and +4.6 (thiol proton)" in the article. I can find sources supporting the 4.6 value, but not for the −1.95 value. Petergans 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 −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)[reply]

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 doi:10.1016/j.jinorgbio.2006.05.003. 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)[reply]
Ref 40 is "R. Alan Jones; A. R. Katritzky (1960). "N-oxides and related compounds. Part XVII. The tautomerism of mercapto- and acylamino-pyridine 1-oxides". J. Chem. Soc.: 2937–2942. doi:10.1039/JR9600002937.". 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)[reply]
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)[reply]

WikiJournal of Science promotion

The WikiJournal of Science is a start-up academic journal which aims to provide a new mechanism for ensuring the accuracy of Wikipedia's scientific content. It is part of a WikiJournal User Group that includes the flagship WikiJournal of Medicine.[1][2]. Like Wiki.J.Med, it intends to bridge the academia-Wikipedia gap by encouraging contributions by non-Wikipedians, and by putting content through peer review before integrating it into Wikipedia.

Since it is just starting out, it is looking for contributors in two main areas:

Editors

  • See submissions through external academic peer review
  • Format accepted articles
  • Promote the journal

Authors

  • Original articles on topics that don't yet have a Wikipedia page, or only a stub/start
  • Wikipedia articles that you are willing to see through external peer review (either solo or as in a group, process analagous to GA / FA review)
  • Image articles, based around an important medical image or summary diagram

If you're interested, please come and discuss the project on the journal's talk page, or the general discussion page for the WikiJournal User group.

  1. ^ Shafee, T; Das, D; Masukume, G; Häggström, M (2017). "WikiJournal of Medicine, the first Wikipedia-integrated academic journal". WikiJournal of Medicine. 4. doi:10.15347/wjm/2017.001.
  2. ^ "Wikiversity Journal: A new user group". The Signpost. 2016-06-15.

T.Shafee(Evo&Evo)talk 10:39, 24 January 2017 (UTC)[reply]

Comment on wikidata transclusion from the User:ProteinBoxBot team

I just realized that I posted this message over on WT:CHEM, 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)[reply]

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

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:

Header text Dataset from DB1 Dataset from DB2 Dataset from DB3 Dataset from DB4
Parameter 1 AA AA AA -
Parameter 2 BB - BB BB
Parameter 3 CC DD CC FF
Parameter 4 EE EE - GG

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)[reply]

One can start with Regression analysis, and ask WP:MATH people? -DePiep (talk) 18:59, 29 January 2017 (UTC)[reply]

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)[reply]

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)[reply]
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)[reply]
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)[reply]
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)[reply]
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)[reply]
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)[reply]

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)[reply]

It gives 3 examples, all structural errors in images. The author (@Mandlerm:) 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)[reply]
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)[reply]
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)[reply]
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)[reply]
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)[reply]
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)[reply]
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)[reply]

Please look at the section "Wiki Howlers" on my personal page. Petergans (talk) 10:30, 2 February 2017 (UTC)[reply]

  • 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 {{Chembox}}, {{Drugbox}}). 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)[reply]
That talk is here, and actually is a fork/continuation of #Big_data_improvement_in_Wikidata here ;-).
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)[reply]
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)[reply]
Thanks for pointing to this article! Very uplifting and energizing. V8rik (talk) 20:57, 5 February 2017 (UTC)[reply]
Thanks for pointing to this article! -DePiep (talk) 23:43, 5 February 2017 (UTC)[reply]
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)[reply]

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)[reply]

Could you give the name of that article? -DePiep (talk) 08:43, 3 February 2017 (UTC)[reply]
@DePiep: single displacement reaction. -- Daniel Mietchen (talk) 08:58, 3 February 2017 (UTC)[reply]
Of course, how could I miss that. ;-) -DePiep (talk) 09:35, 3 February 2017 (UTC)[reply]
  • 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)[reply]
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