Talk:Gold(III) chloride

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Good articleGold(III) chloride has been listed as one of the Natural sciences good articles under the good article criteria. If you can improve it further, please do so. If it no longer meets these criteria, you can reassess it.
Did You Know Article milestones
DateProcessResult
December 10, 2005Good article nomineeListed
March 14, 2007Good article reassessmentDelisted
July 14, 2021Good article nomineeNot listed
April 14, 2023Good article nomineeListed
Did You Know A fact from this article appeared on Wikipedia's Main Page in the "Did you know?" column on May 20, 2023.
The text of the entry was: Did you know ... that gold(III) chloride can directly convert a primary amine to a ketone without any additional steps?
Current status: Good article

A Commons file used on this page or its Wikidata item has been nominated for deletion[edit]

The following Wikimedia Commons file used on this page or its Wikidata item has been nominated for deletion:

Participate in the deletion discussion at the nomination page. —Community Tech bot (talk) 21:08, 11 August 2020 (UTC)[reply]

GA Review[edit]

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This review is transcluded from Talk:Gold(III) chloride/GA1. The edit link for this section can be used to add comments to the review.

Reviewer: RoySmith (talk · contribs) 13:17, 27 May 2021 (UTC)[reply]

I'm starting this review now. My plan is to do two major passes through the article, first for prose, the second to verify the references and more technical aspects. In general, all my comments will be suggestions which you can accept or reject as you see fit.

Lead[edit]

  • I'm confused about, "the name gold trichloride is a simplification". You later mention, when gold dissolves in aqua regia, is sometimes referred to as "gold chloride" or "acid gold trichloride" but these seem in the wrong order. First state that it's called that, then qualify that the name is a simplification.
  • "The Roman numerals in the name indicate", I would just say, "The III in the name indicates....". You already link to oxidation state and people can go there for more details.
  • I would remove the bit about gold(I) chloride from the lede; it doesn't seem essential to understanding the III compound.
  • I'm also confused about Chloroauric acid; is that yet another oxidation state?
  • "Gold(III) chloride is very hygroscopic and highly soluble in water" Is it redundant to say that it's both hygroscopic and soluble? Are they not the same thing? My inorganic chemistry is kind of weak; if there's actually a useful distinction, then it's fine.
    • They are not the really the same thing, solubility is how well the compound dissolves in water and hygroscopicity is how well the compound absorbs water. Keres🌑(talk • ctb) 15:11, 27 May 2021 (UTC)[reply]
  • "decomposes above 160 °C or in light." What kind of light? Visible? UV?
  • As a general statement, the lead should be a summary of what's in the body of the article, per MOS:LEAD. There basically shouldn't be anything in the lead that's not discussed in greater detail in the body, so things like the (I) compounds, it's solubility, or sensitivity to light shouldn't be in the lead because they're not discussed in more detail later.
    • Deleted solubility and decomposition. The sensitivity to light and hygroscopicity is a basic property to a chemical compound so it is good enough to be in the lead. Keres🌑(talk • ctb) 16:02, 27 May 2021 (UTC)[reply]

Infobox[edit]

Structure[edit]

  • You need to briefly explain "d8 electron count". Maybe there's a section in Atomic orbital you can link to?
  • Wikilink "square planar", "solid" and "vapour" to appropriate articles.

Preparation[edit]

Reactions[edit]

  • Terms that need explanation and/or linking: "acidic hydrates", "conjugate base", "aqueous"
  • The layout makes this section difficult to read. The display-formatted equations have lost their indenting, possibly due to the left-aligned image. I'm not sure what the right fix is. Maybe move it (and some of the images from the infox) to a {{gallery}} at the end of the article?
  • "AuCl3 is Lewis acidic", I think would read better as, "...is a lewis acid".

Applications in organic synthesis[edit]

  • "Gold(III) salts, especially Na[AuCl4] (prepared from AuCl3 + NaCl)", is it important to note how they're prepared? Maybe just leave out the parenthetical statement completely?
  • "catalyst" should be linked the first time it's used (and not after that).
  • The way you link tosyl in "(Ts=tosyl)" is hard to read Also, the single sentence after the diagram makes it choppy to read. Maybe rework this as, "phenols sometimes form double-bonds to tosyl groups, i.e. Ts=tosyl, which involves a rearrangement that gives a new aromatic ring", then the diagram.
    • Oh, wait, this is even more confusing than I originally thought. You're not saying "Ts double bond tosyl", you're saying, "Ts is an abbreviation for tosyl"! Yeah, you need to find some way to make that more clear.
  • "to afford the dimeric phenylgold(III) dichloride" "afford" seems like an odd word here. Is it standard chemical usage? Maybe, "to produce..." or "to yield..."
  • "minutes at room temperature", maybe "reaction times of a few minutes at room temperature"?

Additional comments[edit]

Thank you for your quick response to all my items above.

The lead still needs copyediting for English grammar and diction. For example, the second sentence, "With the molecular formula Au2Cl6." isn't a sentence, and "Chloroauric acid, HAuCl4, also has the oxidation state..." looks like it's missing a word ("... WHICH also has the oxidation state"). I note that you're not a native English speaker; I suggest you ask at WP:GOCE for assistance with the writing.

Fixed grammar issues and reworded "common" to "typical". Keres🌑(talk • ctb) 15:46, 28 May 2021 (UTC)[reply]

The lead as currently written also isn't, "a summary of its most important contents", as required by WP:LEAD. I would suggest going through the other sections and picking out the most significant fact from each to include in the lead. For example, I would cover the following points in the lead:

  • It's a dimer.
  • It's commonly prepared either by reacting metallic gold with chlorine gas, or by heating chloroauric acid.
  • Pick one or two items (I'm not sure what) out of the Reactions section to mention briefly.
  • Can be used to catalyze a variety of organic reactions.

As for the other criteria, I'm not seeing any problems with WP:V or the references themselves, or WP:OR. Earwig picks up a bunch of textual matches but they all look like sites that have copied from us.

I think you're ok with "Broad in its coverage". The article seems a little short (and a bit heavy on the tabular infobox vs prose), but there may not be much more to say on this topic. No problems with WP:N or being stable. All the images seem to be appropriately licensed, but the images in the infobox need captions.

Added captions. Keres🌑(talk • ctb) 19:14, 28 May 2021 (UTC)[reply]

I'm going to put this review on hold to give you time to work with the GOCE folks on the language issues.

@RoySmith: Done fixing grammar issues. Please tell me if there is any more. Keres🌑(talk • ctb) 21:40, 28 May 2021 (UTC)[reply]

Next steps[edit]

Keresluna, I'm going to make two specific requests here, both of which I've hinted at earlier. I know I stated earlier that "all my comments will be suggestions which you can accept or reject as you see fit", but I need to be more emphatic about these.

First, please read Wikipedia:Summary style to get a better feel for what the lead should contain. Right now, it's a collection of random facts, not a summary of the contents of the rest of the article.

Second, please list this at WP:GOCE. Your user page indicates that you are not a native English speaker. That's fine. I have great respect for people who learn English as a non-native language. But, your writing could use some cleaning up, and GOCE is specifically set up to improve the quality of text for GA nominations. I can tell you from my own writing experiences, once you've read a paragraph 20 times, you stop seeing the problems. Having a fresh set of eyes look at it is a great way to spot things that you've missed.

@RoySmith: I have a question. What do you exactly mean listing it on WP:GOCE? Keres🌑(talk • ctb) 18:15, 4 June 2021 (UTC)[reply]
Keresluna, You can add a request at Wikipedia:WikiProject Guild of Copy Editors/Requests. Looking at the queue there, it may take a week or two for them to get to it, but I'll be happy to leave this on hold to give them time to review it. -- RoySmith (talk) 18:27, 4 June 2021 (UTC)[reply]
Thanks! Keres🌑(talk • ctb) 18:31, 4 June 2021 (UTC)[reply]
User:Keresluna I have looked through the page and I have copywrited the page to that of comparable standard to similar pages. There seems to be no major red flag in the language part. If you have any feedback please message me on my talk page. EpicSnek Talk to me here 08:29, 22 June 2021 (UTC)[reply]
I see that the first pass of changes from GOCE have been reverted and it's back on the queue for somebody else to make another attempt. That's unfortunate, but it does at least give me a good excuse to extend how long this review is on hold to give you time to work on the other main issue.
While the second round of copy editing is going on, please, as I noted earlier, review Wikipedia:Summary style and in particular MOS:LEAD and rework the lead to be in line with that style guideline. Specifically, note where it says, Significant information should not appear in the lead if it is not covered in the remainder of the article. As one example, the lead says, This compound has two forms: the hydrate and the anhydrous form. There's nothing in the body that says that (nor is it sourced). Likewise, you give the molecular formula of Au2Cl6, but that's not in the body either (or sourced). Ditto for the oxidation state being +3. And The name gold trichloride is a simplification, referring to a lot of compounds needs to be covered (and sourced) in the body. -- RoySmith (talk) 14:21, 24 June 2021 (UTC)[reply]

Second opinion needed[edit]

The biggest issue I see with the article currently is that it still doesn't follow MOS:LEAD, specifically, "significant information should not appear in the lead if it is not covered in the remainder of the article". I'm unsure how strictly I should be holding to this criteria. For example, the lead talks about "oxidation state of +3", which is not mentioned in the body nor supported by reference. Likewise for "molecular formula Au2Cl6". And "decomposes in visible light". Are these issues minor enough that it should pass, or serious enough to fail it? -- RoySmith (talk) 23:30, 12 July 2021 (UTC)[reply]

RoySmith, I think those issues should be addressed in order for the article to pass. The good article criteria expressly state that an article has to "compl[y] with the manual of style guidelines for lead sections". Moreover, an article has to verifiable, and having at least three claims in the lead which have no citation in the article is a cause for concern; indeed, the article was delisted in 2007 due to a lack of citations. It also suggests that there might be an issue of breadth—if claims are thrown into the lead but not discussed in the article, are there other aspects of the topic that have been left out? --Usernameunique (talk) 05:49, 14 July 2021 (UTC)[reply]
@Usernameunique thanks. Based on that, I'm going to fail this review, as this was an issue brought up over a month ago with no significant progress being made towards fixing it. -- RoySmith (talk) 13:06, 14 July 2021 (UTC)[reply]

GA Review[edit]

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This review is transcluded from Talk:Gold(III) chloride/GA2. The edit link for this section can be used to add comments to the review.

Reviewer: Jimfbleak (talk · contribs) 08:03, 8 April 2023 (UTC)[reply]


Keresluna, I'll review this, but it may be a little slow with Easter intervening. Just a couple of drive by comments for now.

  • Some text is unsourced
    • Sourced
  • Capitalise Lewis acid
    • Capitalized
  • Last sentence I think has a grammar error, and can we have a formula for the red-linked compound
    • Fixed.
  • Check wikilinks, eg benzene, nanoparticles, visible light
    •  Done
  • "As of 2003" Do you mean "since 2003" or is this information 20 years out of date?
    • Changed it to 'since 2003'.
  • They are both hygroscopic might be clearer as Both monomer and dimer are hygroscopic
    • Changed to 'the anhydrous and monohydrate are both hygroscopic.'
  • to reform the anhydrous form is a bit clunky
    • Changed the phrase.
  • Gold(III) chloride reacts with benzene (and a variety of other arenes) under mild conditions (reaction times of a few minutes at room temperature) to produce the dimeric phenylgold(III) dichloride:[14] better as Gold(III) chloride reacts with benzene under mild conditions (reaction times of a few minutes at room temperature) to produce the dimeric phenylgold(III) dichloride; a variety of other arenes undergo a similar reaction:[14]
    •  Done
  • tetrabutylammonium chloride, tetrabutylammonium tetrachloraurate. Formulae perhaps?
    • No need, the formula can be determined from the name.
  • Several other apparent book refs don't have page numbers for the referenced text, #9, 10, 12, 13
    • Rm 13, added page numbers for the rest.
  • You twice say it decomposes in light, but don't give the products. Are they the elements or AuCl and Cl2?
  • AuCl - name?
  • ref 3 Worldcat isn't a suitable link, better to have no link at all, especially as you are not linking to any real content. Also needs page numbers
    •  Done
  • I don't think aqua regia is italicised these days
I am still working on that, as I cannot find the decomposition products. Keres🌕Luna edits! 13:48, 9 April 2023 (UTC)[reply]
  • Keres🌕, if you can't find that, that's OK. I'd guess it's the elements, but it doesn't appear to stated anhywhere I've found Jimfbleak - talk to me? 09:08, 10 April 2023 (UTC)[reply]
    Ok, I still cannot find the decomposition products. Do you have any more comments? Keres🌕Luna edits! 21:56, 13 April 2023 (UTC)[reply]

GA review (see here for what the criteria are, and here for what they are not)

  1. It is reasonably well written.
    a. (prose, spelling, and grammar):
    b. (MoS for lead, layout, word choice, fiction, and lists):
  2. It is factually accurate and verifiable.
    a. (reference section):
    b. (citations to reliable sources):
    c. (OR):
    d. (copyvio and plagiarism):
  3. It is broad in its coverage.
    a. (major aspects):
    b. (focused):
  4. It follows the neutral point of view policy.
    Fair representation without bias:
  5. It is stable.
    No edit wars, etc.:
  6. It is illustrated by images and other media, where possible and appropriate.
    a. (images are tagged and non-free content have non-free use rationales):
    b. (appropriate use with suitable captions):
  7. Overall:
    Pass/fail:

(Criteria marked are unassessed)

Did you know nomination[edit]

The following is an archived discussion of the DYK nomination of the article below. Please do not modify this page. Subsequent comments should be made on the appropriate discussion page (such as this nomination's talk page, the article's talk page or Wikipedia talk:Did you know), unless there is consensus to re-open the discussion at this page. No further edits should be made to this page.

The result was: promoted by Bruxton (talk) 19:05, 11 May 2023 (UTC)[reply]

(
)
  • ... that Gold(III) chloride can directly convert a primary amine to a ketone without any additional steps? Source: Coghlan (2015) "Gold(III) chloride" Encyclopedia of Reagents for Organic Synthesis.
    • Reviewed:

Improved to Good Article status by Keresluna (talk). Self-nominated at 17:22, 14 April 2023 (UTC). Post-promotion hook changes for this nom will be logged at Template talk:Did you know nominations/Gold(III) chloride; consider watching this nomination, if it is successful, until the hook appears on the Main Page.[reply]

General: Article is new enough and long enough
Policy: Article is sourced, neutral, and free of copyright problems

Hook eligibility:

  • Cited: Yes
  • Interesting: Yes
  • Other problems: No - not fully mentioned in article.
QPQ: None required.

Overall: @Keresluna: Good article. Though "without any additional steps" looks to be important yet that isn't mentioned in the article. Would like to have you add it before I approve. Onegreatjoke (talk) 22:34, 14 April 2023 (UTC)[reply]

@Onegreatjoke: Done. Keres🌕Luna edits! 23:23, 14 April 2023 (UTC)[reply]
Guess that's fine. Onegreatjoke (talk) 18:31, 15 April 2023 (UTC)[reply]

Caution with app's[edit]

The research literature on gold-based catalysis is voluminous. For this reason, it is prudent to stick to secondary or tertiary literature. All organic chemists want the readers of their publications to conclude that the work is "useful". I could be wrong, but there are zero applications of any of soluble gold complex in the production of any commercial organic compound. Zero. The biggest app for gold remains jewelry, around 80%.--Smokefoot (talk) 23:40, 14 April 2023 (UTC)[reply]

Not all gold goes to the jewelry industry, some gold-based medicine are known and are actively used, such as Auranofin. However, I agree there are very little applications of gold compounds to produce any organic compounds. Keres🌕Luna edits! 02:04, 15 April 2023 (UTC)[reply]
Great. Yes, some antiarthritic drugs and such. I really wish that Au was useful in org syn. Maybe it'll happen, but I wanted to check that you knew. Good luck with the article. Keep it up. --Smokefoot (talk) 03:41, 15 April 2023 (UTC)[reply]

" that Gold(III) chloride can directly convert a primary amine to a ketone without any additional steps?"[edit]

That statement describes a cool transformation. For a chemist, however, the statement requires qualification. The reaction is not very general. No one uses the process. It is stoichiometric. So ca. 300 g of AuCl3 is required to convert 100 g of cyclohexylamine to cyclohexanone that is easier to make otherwise. Chemists are however a critical crowd, and it may well be fun to tell the general audience that gold chloride has some potential as a reagent. --Smokefoot (talk) 23:58, 14 April 2023 (UTC)[reply]

Cyclohexylamine[edit]

Is this article referring to cyclohexylamine as a secondary amine? Edsanville (talk) 13:49, 20 May 2023 (UTC)[reply]

That was a recent vandalism. Fixed. Keres🌕Luna edits! 17:30, 22 May 2023 (UTC)[reply]
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