# Wikipedia talk:WikiProject Chemistry

WikiProject Chemistry (Rated Project-class)
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## Request for information on WP1.0 web tool

Hello and greetings from the maintainers of the WP 1.0 Bot! As you may or may not know, we are currently involved in an overhaul of the bot, in order to make it more modern and maintainable. As part of this process, we will be rewriting the web tool that is part of the project. You might have noticed this tool if you click through the links on the project assessment summary tables.

We'd like to collect information on how the current tool is used by....you! How do you yourself and the other maintainers of your project use the web tool? Which of its features do you need? How frequently do you use these features? And what features is the tool missing that would be useful to you? We have collected all of these questions at this Google form where you can leave your response. Walkerma (talk) 04:24, 27 October 2019 (UTC)

## Shameful self promotion

Self promotion seems to be a big issue with plenty of computational chemistry articles. One only needs to look at various lists on articles like Molecular_dynamics#Examples_of_applications or Force_field_(chemistry)#Popular_force_fields. Now some of these genuinely represent notable advances or popular forcefields in the case of the second example, however a great deal do not... Most are based on primary literature. Should we delete lists like this replacing them with short paragraphs based on review articles? EvilxFish (talk) 16:44, 28 October 2019 (UTC)

You should see the self-promotion in the synthesis areas. About two cases per week, I reckon. Here is my approach:
1. ) if the self-promotor adds their ref to an article lacking citations, I leave the ref, even if the self-promoting ref is primary. The theory is something is better than nothing. Later, time-permitting, I try to find a secondary article to replace the promotor's article (I do not want self-promotors to feel rewarded).
2. ) if the self-promoting article already has a foundation of a decent refs, I revert self-promotors.
3. ) I check the history of self-promotors, and try to apply rules 1 and 2 above to their other edits.
• The overarching worry is that some of these self-promotors, if treated in a welcoming way, will become good contributors. (the concept: "don't bite newbies" or something like that) Almost never have I seen self-promotors do good. Self-promotors come here to promote themselves, period. It seems.
• One surprise is that self-promotion is also practiced by senior, established scientists.--Smokefoot (talk) 22:06, 28 October 2019 (UTC)
I disagree in part with Smokefoot. Even if the article lacks other citations you should still delete self-promotion. It can be difficult to spot and if you ignore it you may eventually forget about it. If you feel that refs are necessary but can't find/access any then just flag it here, I'm sure we'll act in those circumstances. Of more concern to me are whole articles that appear to be self-promotional such as Matthew Linford or Sean Ekins, it feels like we have more articles on living chemists than dead ones, and that can't possibly be right. --Project Osprey (talk) 07:16, 29 October 2019 (UTC)
I feel as if the entire lists are not necessary, genuine advances will/should be covered in the history section of the article and they are just opening the door to easy abuse (not exactly hard to add an element to a list with a brief summary of your own work). Should we just delete the entire section? As for the bios let's nominate them for deletion, I will certainly vote in favour. Honestly wikipedia is a tool all academics use (whilst hypocritically condemning it as unreliable) and seeing them abusing it like this is very frustrating. EvilxFish (talk) 09:53, 29 October 2019 (UTC)
In Molecular dynamics any genuinely important refs from "Examples of applications" could be added back in at "Areas of application" or maybe "History" and the section deleted. In Force field (chemistry) "Popular force fields" could be largely copied over to "Comparison of force field implementations", maybe leave a short paragraph to cover the basics. That's just my opinion though. --Project Osprey (talk) 11:31, 29 October 2019 (UTC)

### Example of the day

Here is a typical ref-spamming case from . This editor made these edits, today or in 2015:

Zeeman slower

[1][2][3] and a series of identical connected coils.[4]

Zeeman slower (2015) edit

The most common approach is to require that we have a magnetic field profile that varies in the ${\displaystyle z}$ direction such that the atoms experience a constant acceleration ${\displaystyle a=\eta a_{max}}$ as they fly along the axis of the slower. It has been recently shown however, that a different approach yields better results.[5]

Photofragment-ion imaging

One of the recent advancements in the field is the merger of velocity map imaging with ion[6], and atom traps (MOT-VMI[7]), enabling to study electron emission from trapped cluster anions , and cold reactive collisions.

Isotopic shift

One of the recent advancements in the field is the merger of velocity map imaging with ion[8], and atom traps (MOT-VMI[9]), enabling to study electron emission from trapped cluster anions , and cold reactive collisions.

Magneto-optical trap

Combined with velocity-map-imaging, a MOT was used to study the energetics of cold reactive collisions.[10]

Inductively coupled plasma (2015 edit)

Exciting a beam of noble gas to the metastable state.[11]

Lambert W-function (2015 edit)

The Lambert W function have been recently shown to be the optimal solution for the required magnetic field of a Zeeman slower.[12]

--Smokefoot (talk) 12:27, 29 October 2019 (UTC)

References

1. ^ Reinaudi, G.; Osborn, C. B.; Bega, K.; Zelevinsky, T. (2012-03-20). "Dynamically configurable and optimizable Zeeman slower using permanent magnets and servomotors". Journal of the Optical Society of America B. 29 (4): 729. doi:10.1364/josab.29.000729. ISSN 0740-3224.
2. ^ Lebedev, V; Weld, D M (2014-07-28). "Self-assembled Zeeman slower based on spherical permanent magnets". Journal of Physics B: Atomic, Molecular and Optical Physics. 47 (15): 155003. doi:10.1088/0953-4075/47/15/155003. ISSN 0953-4075.
3. ^ Krzyzewski, S. P.; Akin, T. G.; Dahal, Parshuram; Abraham, E. R. I. (2014-10). "A clip-on Zeeman slower using toroidal permanent magnets". Review of Scientific Instruments. 85 (10): 103104. doi:10.1063/1.4897151. ISSN 0034-6748. Check date values in: |date= (help)
4. ^ Ohayon, Ben; Ron, Guy (2015-10). "Investigation of different magnetic field configurations using an electrical, modular Zeeman slower". Review of Scientific Instruments. 86 (10): 103110. doi:10.1063/1.4934248. ISSN 0034-6748. Check date values in: |date= (help)
5. ^ B Ohayon., G Ron. (2013). "New approaches in designing a Zeeman Slower". Journal of Instrumentation. 8 (02): P02016. doi:10.1088/1748-0221/8/02/P02016.
6. ^ Saha, K; Prabhakaran, A; Rappaport, M L; Heber, O; Schwalm, D; Zajfman, D (2015-09-07). "A VMI setup to study prompt and delayed electron emission from trapped cluster anions". Journal of Physics: Conference Series. 635 (11): 112103. doi:10.1088/1742-6596/635/11/112103. ISSN 1742-6588.
7. ^ Ohayon, B.; Rahangdale, H.; Chocron, J.; Mishnayot, Y.; Kosloff, R.; Heber, O.; Ron, G. (2019-08-06). "Imaging Recoil Ions from Optical Collisions between Ultracold, Metastable Neon Isotopes". Physical Review Letters. 123 (6). doi:10.1103/physrevlett.123.063401. ISSN 0031-9007.
8. ^ Saha, K; Prabhakaran, A; Rappaport, M L; Heber, O; Schwalm, D; Zajfman, D (2015-09-07). "A VMI setup to study prompt and delayed electron emission from trapped cluster anions". Journal of Physics: Conference Series. 635 (11): 112103. doi:10.1088/1742-6596/635/11/112103. ISSN 1742-6588.
9. ^ Ohayon, B.; Rahangdale, H.; Chocron, J.; Mishnayot, Y.; Kosloff, R.; Heber, O.; Ron, G. (2019-08-06). "Imaging Recoil Ions from Optical Collisions between Ultracold, Metastable Neon Isotopes". Physical Review Letters. 123 (6). doi:10.1103/physrevlett.123.063401. ISSN 0031-9007.
10. ^ Ohayon, B.; Rahangdale, H.; Chocron, J.; Mishnayot, Y.; Kosloff, R.; Heber, O.; Ron, G. (2019-08-06). "Imaging Recoil Ions from Optical Collisions between Ultracold, Metastable Neon Isotopes". Physical Review Letters. 123 (6). doi:10.1103/physrevlett.123.063401. ISSN 0031-9007.
11. ^ Ben Ohayon, Erik Wahlin and Guy Ron (2015). "Characterization of a metastable neon beam extracted from a commercial RF ion source". 10 (03). Journal of Instrumentation, Cambridge: P03009. ISBN 1748-0221-10-03-P03009 Check |isbn= value: invalid character (help). Cite journal requires |journal= (help)
12. ^ {{cite journal |last1= G Ron |first1=B Ohayon. |title=New approaches in designing a Zeeman Slower |journal=Journal of Instrumentation |volume=8 |issue=02 |pages=P02016 |year=2013 |doi=10.1088/1748-0221/8/02/P02016 }

## Liquid Nitrogen

Recently an WP:ER was made at Liquid nitrogen to change the name of the 'first liquefied by'. I had a look through, but I know nothing about this subject, and I think a 2006 edit may have caused a WP:CIRCULAR effect. Can someone check and see what needs fixing at LN, Liquid oxygen and Raoul Pictet (if applicable)? Thanks for your help. - ChrisWar666 (talk) 19:09, 28 October 2019 (UTC)

Anyone? - ChrisWar666 (talk) 00:36, 1 December 2019 (UTC)

## Nomination for deletion

I have nominated a few articles chemistry related articles for deletion: MARTINI, Merck Molecular Force Field, X-Pol: the Explicit Polarization Theory, Please contribute to the discussion. Many thanks EvilxFish (talk) 16:06, 29 October 2019 (UTC)

MARTINI, has been reslisted in afd due to lack of consensus, please contribute to this discussion. EvilxFish (talk) 12:05, 7 November 2019 (UTC)

## Fixing chemistry typos

At Wikipedia:Correct typos in one click, you can fix typos or tag them for attention in a single click. However, there are a lot of chemistry terms that we need help with. Can anyone help out with checking whether the typos relating to chemicals are indeed typos? Thanks! Bellowhead678 (talk) 09:16, 6 November 2019 (UTC)

Well, one term that could be searched is "fully miscible" to be replaced with "miscible". But Wikipedian chemists would need to achieve consensus on whether miscibility is a "binary property": two liquids either are or are not miscible. IUPAC and Britannica diverge on the binary-ness of this definition. See Talk:Acetic acid#Miscible is incorrectly used here..--Smokefoot (talk) 13:03, 6 November 2019 (UTC)
Thanks, I meant just for people to go through the existing list and check whether the suspected typos are indeed typos. Bellowhead678 (talk) 14:02, 6 November 2019 (UTC)
I am checking, but most of the chemistry terms are correct. I am adding some things to Wiktionary, but some may usefully be redirects. A question for people here for : 11β-trihydroxy-5α-ergost-22(E)-en-6-one , should the "E" be in parenthesis? and for ergost and ergosta we could do with a Wiktionary entry. (I think the original in the typos listing is correct though). Graeme Bartlett (talk) 22:01, 6 November 2019 (UTC)
Thanks, there are several additional lists to check through if you have gone through the main page. Bellowhead678 (talk) 22:22, 6 November 2019 (UTC)
So what lists are those? Are these with a number suffixed like Wikipedia:Correct typos in one click/19? I did notice that this one click task fixed some typos I made. Graeme Bartlett (talk) 22:28, 6 November 2019 (UTC)
Yes that's right, you can see them at the top of the main list. Bellowhead678 (talk) 00:02, 7 November 2019 (UTC)
All chemistry words now look to be finished. When will more come? Graeme Bartlett (talk) 11:39, 8 November 2019 (UTC)
It's up to Uziel302 who runs the page, but probably once all the current typos have been fixed. (I would also like it to be sooner rather than later!) Bellowhead678 (talk) 11:55, 8 November 2019 (UTC)
, I uploaded new list now, based on words I found on chemistry books, so many will be chemistry typos. Uziel302 (talk) 01:04, 9 November 2019 (UTC)
Quite a few of these have already been fixed in the last few days, is this an out of date database dump?
Do we have a ref that the name is correctly laid out with the "E" in the middle of the name at all? Usual convention is that stereochemical designators go as a prefix not infix. DMacks (talk) 07:02, 7 November 2019 (UTC)

## Homework discussions on Talk

I confess to not being a fan of unsupervised homework assignments involving Wiki Chem articles, but it is what it is ... The aspect that I do question and have recently reverted are students using Talk pages to debate their edits. But maybe I am overstepping. My view: Talk pages are exclusively about improving articles and comments are addressed to the entire editor-universe. In contrast, homework discussion groups are:

• private conversations for a small working group (regular editors are not invited),
• have an agenda that differs from Wikipedia's. The agenda is set by the instructor,
• suffer from " the blind leading the blind" phenomenon: inexperienced editors instructing other inexperienced editors.
--Smokefoot (talk) 12:29, 7 November 2019 (UTC)
Well perhaps you should respond to their talk. Don't worry that they think it's private. Steer them onto what is appropriate for Wikipedia. Give an opinion on the proposed edits, even it it is try it out and if I don't like it I will remove it. Graeme Bartlett (talk) 21:46, 7 November 2019 (UTC)
I see now there is a main group chemistry class writing and drawing electron cloud images. See here https://dashboard.wikiedu.org/courses/MIT/Main_Group_Chemistry_(Fall)/students for the users and their pages. Though at this stage it looks like only Trivalent group 14 radicals has made it to article status. Graeme Bartlett (talk) 11:23, 24 November 2019 (UTC)
Sandboxes here: User:Tristan-Xin/sandbox=Nontrigonal pnictogen compounds; User:Alkemiya/sandbox=Ge(II) dications; User:SWeng19/sandbox=borenium User:BASkeel/sandbox=phosphaalkyne; User:Paperburner/sandbox=boroles; User:Tetraphenylporphine/sandbox/Triboracyclopropenyl Graeme Bartlett (talk) 10:06, 30 November 2019 (UTC)

## Category:Pyridoisoquinolines and ring counting

Hello, last month this CfD involving Category:Pyridoisoquinolines was closed with a consensus to merge manually to parents. All articles seem to be about nitrogen hetrocycles, no problem there, however I'm a bit confused whether all of them are appropriate for Category:Heterocyclic compounds (3 rings), as far as I can tell most have 5 rings. Could someone help me out and clarify how this ring counting is done? ‑‑Trialpears (talk) 22:12, 20 November 2019 (UTC)

We need a top-note on the Heterocyclic compounds (n rings) to say how the rings are counted. Is it the total number of rings, or the number of fused rings? I assumed the latter, in which case most of those compounds would go to both Heterocyclic compounds (3 rings) and Heterocyclic compounds (2 rings). This would be equivalent to tricyclo and bicyclo compounds. Graeme Bartlett (talk) 23:25, 20 November 2019 (UTC)

## Nominated article on chemist for deletion.

Nominated Nathan C. Gianneschi for deletion, agreed when this was in draft space that it should be deleted. Please contribute to the discussion. EvilxFish (talk) 12:58, 23 November 2019 (UTC)

Once these biographical articles get into main space, they are almost impossible to stop. The article was created by someone at the same institution who had been promoting Gianneschi's work previously. Its just the way that it is. There are more useful ways of expending our energy here. --Smokefoot (talk) 13:08, 23 November 2019 (UTC)
Regardless of the origin of the article, the subject appears to meet our notability guidelines so we should have an article about him. In my opinion, problems related to self-promotion or other conflicts of interest can be better solved by editing and improving the article rather than by deleting it. -- Ed (Edgar181) 13:23, 23 November 2019 (UTC)
Basic XfD: Discussion should only be performed at Wikipedia:Articles for deletion/Nathan C. Gianneschi. The creator should be notified. -DePiep (talk) 14:31, 23 November 2019 (UTC)

As an aside, I've long thought that WP:PROF needs to be radically tightened.--Project Osprey (talk) 21:03, 24 November 2019 (UTC)

## Forging temperatures are wrong

The explanation on the forging temperature page is great, but the temperatures are wrong. It lists melting points, not forging temperatures. — Preceding unsigned comment added by 73.71.254.108 (talk) 04:46, 30 November 2019 (UTC)

Thanks, I changed the headings on Forging temperature to have correct info, even if it is useless for this article. Graeme Bartlett (talk) 09:56, 30 November 2019 (UTC)

## New organic chemistry 3D resources

Please see https://qrchem.net and https://rschemistry.com which were just announced. EllenCT (talk) 06:18, 6 December 2019 (UTC)

Thanks for the heads-up! Do you have any contact with the people working on the qrchem project? There is at least one pattern of substantial mistakes in some of the structures, which we found years ago and they are only now starting from the same square one. DMacks (talk) 16:50, 6 December 2019 (UTC)
There is a contact page in the menu dropdown or you could try contacting Garg directly thru UCLA. YBG (talk) 01:16, 7 December 2019 (UTC)

Please help decide what to do with alkine, thanks. The Language Learner (talk) 21:53, 11 December 2019 (UTC)

## Non-helical models of DNA structure

I saw a Science Reference Desk question about this article. I've edited some of the references but have concerns about the content in this article. I've started a discussion at Talk:Non-helical models of DNA structure#Work from X, Y. C. about my concerns. Any and all comments, edits, etc welcome. Thanks, EdChem (talk) 04:13, 13 December 2019 (UTC)

## Question at hexavalent chromium

Would someone look at Talk:Hexavalent chromium#Lead wrong? Thanks. —[AlanM1(talk)]— 07:06, 26 December 2019 (UTC)

## Citation bot is down

This handy tool is not working lately. See User talk:Citation bot.--Smokefoot (talk) 15:22, 28 December 2019 (UTC)

## Tetrakis(methylammonium) hexachloroferrate(III) chloride

I notice that we have an article on tetrakis(methylammonium) hexachloroferrate(III) chloride, (CH
3
NH+
3
)
4
[FeCl
6
]
Cl
(or possibly (CH
3
NH
3
)
3
[FeCl
6
]·CH
3
NH
3
Cl
). The image accompanying the infobox is File:Tetrakis(methylammonium)hexachloroferratechloride.svg which shows the heachloroferrate with a 3− charge on the iron centre, surrounded in what appears to be a square planar arrangement by methylammonium cations. This is (at best) misleading. Can someone provide a replacement? The uploader of the image was Ronhjones in 2010 but, according to his global contributions, he last contributed in April 2019. Thanks. EdChem (talk) 03:01, 3 January 2020 (UTC)

Looks ok to me. Its a strange one in that there free chloride in the lattice. Agreed that we dont want readers to reach any special conclusions about the location of the MeNH3+ cations in the picture. Some odd ducks (i.e. their notability being arguable) get written up in Wikipedia, and this is one. It might be worthwhile if other editors look at double salt to make sure we are in consensus. --Smokefoot (talk) 03:39, 3 January 2020 (UTC)
I think it's a mistake that the "3–" looks like it's associted with the Fe itself rather than the [FeCl6] cluster. It's actually weirder than that...not "free chloride in the lattice", but effectively "a [(CH3NH3)4Cl]3+ complex" (I just updated the article based on the cited X-ray structure ref). And based on that, I think it is a mistake to have all the methylammoniums and the chloride as loose separate ions. DMacks (talk) 03:45, 3 January 2020 (UTC)
In crystalline FeSO4.7H2O, the first coordination sphere of Fe2+ consists of six water ligands. The second coordination sphere consists of a water of crystallization and sulfate, which interact with the [Fe(H2O)6]2+ centers.
Editors here are rediscovering the wheel: ammonium ions (those with N-H) virtually always H-bond. Similarly, naked chlorides and esp fluorides virtually dont exist. M-NH3 complexes (metal ammine complexes) and M-OH2 complexes (metal aquo complexes)) universally engage in H-bonding to their anions (chloride, sulfate). Think hexamminecobalt(III) chloride. H-bonding confers high lattice energies, i.e. have high m.p.'s, crystallinity, etc. By depicting these multiple H-bonding networks, the images would be very messy. So, by tradition, the first coordination sphere is emphasized in our images, not the second. So a few of us specialists might be satisfied with these fancier images, but the more general readers would be completely lost. For tetrakis(methylammonium) hexachloroferrate(III) chloride, it doesnt matter because that salt is inconsequential. --Smokefoot (talk) 09:52, 3 January 2020 (UTC)
The edits made today by DMacks add further reasons to consider the existing image problematic. The interstitial chloride ions are each surrounded by four methylammonium cations to form a [(CH
3
NH
3
)
4
Cl]3+
unit, something entirely obscured (at best) by the image, which implies no association between the chloride and methylammonium ions. Smokefoot is correct about the coordination spheres and that the salt is relatively inconsequential. The H-bonding is at best vaguely implied in the current image, however. Surely we can think of a better representation without going to something so complicated that it is only comprehensible to chemists? EdChem (talk) 11:58, 3 January 2020 (UTC)

## Mct

I was looking at the article about Medium-chain triglyceride. It is very confusing; mixing information of triglycerides with information of acids and not relating them to each other and not clerify if one of them are natural and the other manmade.

The first sentence."Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids" Is it true? Or maybe they are called diglycerides if they are with two fatty acids?

Sentence two. "Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil" Are MCT really extracted from oils or is it more like medium chain fatty acids ( acids instead of triglycerides) are extracted and then exposed for chemical processes to make triglycerides? There might or might not be small amounts of triglycerides naturally occuring? But everything available in the market is manmade chemicals.

The marketing of MCT is huge. So it is important the wiki is not confusing us, the customers. From this article a customer might think that MCT is something natural. Please clerify.Oloffo (talk) 06:19, 7 January 2020 (UTC)

the first sentence definitely says it is a triglyderide, so if there are 2 medium chain acids only, then there must be a third of something else, probably a long chain fatty acid. Don't insert your full stop too early! Our article does not say how they are "made", but it is likely a simple extraction from a natural source. Why make the process expensive? Graeme Bartlett (talk) 12:07, 7 January 2020 (UTC)
Axona was intended for medical use and that was just fractionated palm kernel oil. I agree with Graeme Bartlett that natural sources seem the most likely.--Project Osprey (talk) 13:13, 7 January 2020 (UTC)

## Merck Index citations

There was consensus, back in 2015 (when I was Wikimedian in Residence at the Royal Society of Chemistry), for this proposal to replace three Merck templates ({{Merck11th}}, {{Merck12th}}, {{Merck13th}}) with {{Cite Merck Index}}; however that never seems to have happened. It needs the involvement of chemists, as in each case the data needs to be verified and if necessary updated. The there templates have 13, 20 and 8 (eight) transclusions respectively, so it's not a mammoth task. Can anyone oblige? Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 16:37, 18 January 2020 (UTC)

As I recall, the consensus among us chemists was that it was fairly dubious, which might explain the lack of action. I don't have access to the The Merck Index so I'm unable to help. --Project Osprey (talk) 21:04, 19 January 2020 (UTC)
You recall incorrectly; consensus is recorded at the first link in my post. Andy Mabbett (Pigsonthewing); Talk to Andy; Andy's edits 23:00, 20 January 2020 (UTC)

## A link to a DAB page

Does anyone know which of the Wittig rearrangements is being referred to in Radical clock? Narky Blert (talk) 16:38, 20 January 2020 (UTC)

Went back to the 1976 JACS reference that the other reference was referring to, and appears to be a 1,2-Wittig (doi.org/10.1021/ja00422a041). Have fixed the disambiguation and added in the extra citation RRBinwood (talk) 17:31, 20 January 2020 (UTC)
Thanks! I was guessing 1,2, but it's good to be sure. (1976 is a bit after my time.) Narky Blert (talk) 18:43, 20 January 2020 (UTC)

## Draft:Lithium gold boride

Can someone please review this draft? My concern is that the only two references are by the same two authors, which is close to original research. Also, the draft does not list a CAS number, either in an infobox (which is not required and is not present) or in the text, and the lack of a CAS number for what would seem to be a compound makes me wonder about verifiability. Robert McClenon (talk) 02:59, 21 January 2020 (UTC)

For a draft it's not badly written but I don't think it's sufficiently notable. It's primary use is proposed as being "superconducting batteries" but that term is virtually unheard of in the literature. It's calculated as being a superconductor below ∼5.8 K which is far from impressive, it's actually worse than lead. Unless they can show a notable property I'd decline. --Project Osprey (talk) 10:16, 21 January 2020 (UTC)