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WikiProject Chemistry (Rated Project-class)
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Liquid NitrogenEdit

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)

Homework discussions on TalkEdit

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)

Forging temperatures are wrongEdit

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 resourcesEdit

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)

Input at alkine pleaseEdit

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

Non-helical models of DNA structureEdit

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 chromiumEdit

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

Citation bot is downEdit

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

Tetrakis(methylammonium) hexachloroferrate(III) chlorideEdit

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)

MctEdit

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 citationsEdit

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 pageEdit

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 borideEdit

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)

Example: Tishchenko reactionEdit

Many of our articles, especially ones about classic organic chemistry, start with heavy reliance on historic references. We can all be grateful to the editors that put these articles in place and felt it appropriate to pay homage to the pioneers of chemistry. But realistically, moderrn readers are unlikely to want to consult the original work by Vyacheslav Tishchenko when they read about the Tishchenko reaction. They would rather read

  • Seki, Tsunetake; Nakajo, Tetsuo; Onaka, Makoto (2006). "The Tishchenko Reaction: A Classic and Practical Tool for Ester Synthesis". Chemistry Letters. 35 (8): 824–829. doi:10.1246/cl.2006.824.

not

So I suggest that we aim shift the historic, original references out of the ledes and into other sections such as "Other reading" or "History", etc. The early refs will be retained, but an overall effort will be to support the lede with broad, modern sources, often textbooks like Carey or March.--Smokefoot (talk) 01:39, 6 February 2020 (UTC)

Sounds reasonable. I would tend to include cites to the originals in a sentence such as:
The reaction is named for Vyacheslav Tishchenko, who first reported it in 1906.<ref>[cite the original works]</ref>
I could even envision having that sentence in the lede, since it does summarize a bunch of details that would be in the article, placing the reaction in the context of person and time. I would want to include "name reaction" in that sentence (unpiped, since it's a topic known by that term) but I can't think how without being redundant ("a name reaction named for..."?). DMacks (talk) 07:34, 6 February 2020 (UTC)
Depends. For non-eponymous pages like toluene I don't mind (providing we don't create a section that's just "Is named after..."). If the reaction or substance is named after someone it seems odd not to mention who in the lead. --Project Osprey (talk) 09:33, 6 February 2020 (UTC)

Maybe these pages need to be mergedEdit

BTW, I've linked List of isomers of decane to C10H22 pages of French and Chinese in wikidata. I wonder if this page is best in the form of a list or in the form of disambiguation.--Htmlzycq (talk) 07:26, 6 February 2020 (UTC)

On its face, these seem like reasonable proposals, but when I look closer:
  • List of isomers of nonane is a MOS mess...links in headers and duplication of links. It uses strictly systematic names, which is good if that's what you have, but it's not a proper listing in DAB terms because some of the articles do not use systematic name as their title (DAB says we don't pipe) and they are almost all redlinks (hard to find our actual aricles). And why only include structural (vs stereo) isomers, given that sometimes for other chemical-sets each separate stereoisomer of a compound has its own article. I'm not sure that list article should exist, but if it does, it fits a different niche than the formula one. DMacks (talk) 07:48, 6 February 2020 (UTC)
I think if we connected List of isomers of nonane to fr:C9H20 in frwiki, which lists all stereo isomers, it will help to improve this page.--Htmlzycq (talk) 11:34, 6 February 2020 (UTC)
  • 1,1-Diphenylethylene is not a stilbene or stilbenoid in the classical sense. So stilbene is a defined set that is the parent of one major larger class of compounds, and diphenylethylene includes something that is not part of that class. So neither is a subset of the other.
So I don't think either is a case to merge, based on Wikipedia:Set index articles and related DAB/list guidelines. DMacks (talk) 07:48, 6 February 2020 (UTC)
I reckon that C9H20 may as well redirect to List of isomers of nonane. However I sould like to see the list sourced to prove that it is a complete list. Some other languages have rticles on every isomer. But their content and sourcing certainly don't prove that every isomer is notable. So the number of links should be cut. The MOS mess was fixed easily, as those links in the headers are not useful. Graeme Bartlett (talk) 02:40, 9 February 2020 (UTC)

Organising the metals and nonmetalsEdit

FYI: Here's a link to an open access article of the same name, authored by me, and recently published in Foundations of Chemistry. Sandbh (talk) 04:06, 12 February 2020 (UTC)

So does that mean that you should avoid citing this work (in Wikipedia), since doing so would be a COI? Smokefoot (talk) 19:49, 15 February 2020 (UTC)

Please see WP:SELFCITE. Sandbh (talk) 21:28, 15 February 2020 (UTC)

4f sub-shell involvement in lanthanumEdit

Is this possible?

MacKay et. al (2002, p. 256) speculate that:

"The one case in which contributions to the bonding from the f orbitals is possible is in complexes of the heavier elements in which the coordination number is high. Use of the s orbital, together with all the p and d orbitals or one valency shell, permits a maximum coordination number of nine in a covalent species. Thus, higher coordination numbers imply either bond orders less than unity or else use of the f orbitals In addition, certain shapes (such as a regular cube) or lower coordination number also demand use or f orbitals on symmetry grounds. These higher coordination numbers have only become clearly established recently, but their occurrence in lanthanide or actinide element complexes suggest the possibility of f orbital participation. Examples include the 10-coordinate complexes mentioned above, LaEDTA(H2O)4 and Ce(NO3)52- or 10-coordinate La2(CO3]3.8H2O; 11-coordinate Th(NO3)4.5H2O (coordination by four bidentate nitrate groups and three of the water molecules); and the 12-coordinate lanthanum atoms in La2(SO4)3.9H2O-with twelve sulfate O atoms around one type of La atom position."

— MacKay KM, MacKay RA &Henderson W 2002, Introduction to modern inorganic chemistry, 6th ed., Nelson Thornes, Cheltenham

OTOH, Parish (1977, p. 151) firmly rules this out:

"Two features are particularly striking in the chemistry of the 4f—elements, Viz. (a) the uniformity of the +3 oxidation state and the small number of other oxidation states, and (b) the irregularity of structures and occurrence of high coordination numbers. In the compounds described here, coordination numbers of six, seven, eight, and nine have been mentioned, and in other compounds ten- and even twelve-coordinate metal ions are found, eg. in La2(SO4)3.9H20 and (NH4)2Ce(NO3)6. It is tempting to think that the f-orbitals must be involved in the bonding, since the maximum number of hybrid orbitals which can be constructed from an s-p-d -set is nine, and to obtain eight bonding orbitals directed towards the corners of a cube (as in C602) requires at least one f-orbital. There is, however, no evidence to suggest that the f-orbitals are involved at all in the bonding, and even ligand-field effects are extremely small. All the compounds appear to be essentially ionic, with very little covalency involving even the 6s- or 6p-orbitals. The curious structures and high coordination numbers are similar to those found with other large cations (e.g. salts of Ba2+ or Pb2+) and are presumably a result of the optimisation of electrostatic forces. The large internuclear distances necessitated by the radii of the cations will cause the electrostatic energy per pair of ions to be relatively small, despite the high cationic charge, and many such pairs must be formed to achieve a sufliciently large lattice energy. Similarly, the large radii diminish considerably the polarising effect of the +3 charge which would otherwise be expected to lead to considerable covalency." (p. 151) — Parish RV 1977, The metallic elements, Longman, London

Thank you, Sandbh (talk) 22:51, 14 February 2020 (UTC)

With the first 4f6s2 excited state at 1.8842 eV, well within the range of chemical bond energies? Yes, of course. Double sharp (talk) 00:25, 15 February 2020 (UTC)

Are there any other views in this matter, particularly the contradiction between the two cited references? Sandbh (talk) 03:25, 28 February 2020 (UTC)

Script to detect unreliable sourcesEdit

I have (with the help of others) made a small user script to detect and highlight various links to unreliable sources and predatory journals. The idea is that it takes something like

  • John Smith "Article of things" Deprecated.com. Accessed 2020-02-14. (John Smith "[https://www.deprecated.com/article Article of things]" ''Deprecated.com''. Accessed 2020-02-14.)

and turns it into something like

It will work on a variety of links, including those from {{cite web}}, {{cite journal}} and {{doi}}.

I'm still expanding coverage and tweaking logic, but what's there already works very well. Details and instructions are available at User:Headbomb/unreliable. Questions, comments and requests can be made at User talk:Headbomb/unreliable. Headbomb {t · c · p · b} 13:01, 19 February 2020 (UTC)

Issues with CAS Number and ECHA InfoCard in my InfoboxEdit

I asked this same questions in my Sandbox talk page User_talk:Gabriele_Segalla but I'm been suggested to ask this WikiProject Chemistry page too. I have created a Sandbox User:Gabriele_Segalla/sandbox for a chemical and I have created an infobox as well. In the infobox I have two issues:

  1. The CAS number does not work, by clicking it I get (correctly) in the Common Chemistry Website but it states Your Search Returned Zero Results. How can I handle this?
  2. The Input from Wikidata section of the Template:Chembox states that "ECHA InfoCard ID is read from Wikidata", yet I do not see the ECHA InfoCard in the infobox. Again, how can I handle this?

Thank you. --Gabriele Segalla (talk) 08:01, 20 February 2020 (UTC)

Regarding the CAS# Commons Chemistry lookup, it fails for virtually every chemical; I wouldn't worry about it. I do not know anything about ECHA in particular and very little about wikidata item lookups technical details. DMacks (talk) 08:13, 20 February 2020 (UTC)
  • Can we just remove the link to Commons Chemistry? For me at least, all it does is make the CAS N° difficult to copy and paste. --Project Osprey (talk) 10:16, 20 February 2020 (UTC)
I would support unlinking the CAS. Maybe the link was more appropriate in the early days of the ChemBox validation project when we collaborated with some CAS-related external entities, but that was a decade or more ago and now it's not a positive (useless) and is a negative (providing a link to a useless target and interfering with a different useful action like copying). DMacks (talk) 16:57, 20 February 2020 (UTC)
  • The ECHA infocard is only going to appear in the chembox, when the page is linked to the Wikidata item. For drafts and sandboxes this is not a good idea. Graeme Bartlett (talk) 21:48, 20 February 2020 (UTC)
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