# Talk:Gold(III) chloride

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

AuCl3 furan alkylation.gif
Participate in the deletion discussion at the nomination page. —Community Tech bot (talk) 21:08, 11 August 2020 (UTC)

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)
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
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.
Done. Keres🌑(talk • ctb) 15:03, 27 May 2021 (UTC)
"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.
Done. Keres🌑(talk • ctb) 15:03, 27 May 2021 (UTC)
I would remove the bit about gold(I) chloride from the lede; it doesn't seem essential to understanding the III compound.
Done. Keres🌑(talk • ctb) 15:08, 27 May 2021 (UTC)
I'm also confused about Chloroauric acid; is that yet another oxidation state?
Added a description. Keres🌑(talk • ctb) 15:08, 27 May 2021 (UTC)
"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)
"decomposes above 160 °C or in light."  What kind of light?  Visible?  UV?
Added specific kind. Keres🌑(talk • ctb) 16:02, 27 May 2021 (UTC)
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)


### Infobox
See Special:Diff/1025425583


### Structure
You need to briefly explain "d8 electron count".  Maybe there's a section in Atomic orbital you can link to?
Just added a link. Keres🌑(talk • ctb) 16:08, 27 May 2021 (UTC)
Wikilink "square planar", "solid" and "vapour" to appropriate articles.
Done. Keres🌑(talk • ctb) 16:12, 27 May 2021 (UTC)


### Preparation
explain and/or link "lipophilic"
Linked. Keres🌑(talk • ctb) 16:16, 27 May 2021 (UTC)


### Reactions
Terms that need explanation and/or linking: "acidic hydrates", "conjugate base", "aqueous"
Done. Keres🌑(talk • ctb) 00:17, 28 May 2021 (UTC)
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?
Changed it to right-aligned. Keres🌑(talk • ctb) 00:19, 28 May 2021 (UTC)
"AuCl3 is Lewis acidic", I think would read better as, "...is a lewis acid".
Done. Keres🌑(talk • ctb) 00:21, 28 May 2021 (UTC)


### Applications in organic synthesis
"Applications in organic synthesis", add {{asof}}
Done. Keres🌑(talk • ctb) 00:34, 28 May 2021 (UTC)
"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?
Removed statement. Keres🌑(talk • ctb) 00:34, 28 May 2021 (UTC)
For the included images (i.e. File:Example of gold-catalyzed alkyne hydration reaction.svg), I think the layout would work better if they were centered.  But, I'm not that familiar with chemistry articles, so if what you've got is standard practice, that's fine.
That is standard practice. Keres🌑(talk • ctb) 00:34, 28 May 2021 (UTC)
"catalyst" should be linked the first time it's used (and not after that).
Done. Keres🌑(talk • ctb) 00:40, 28 May 2021 (UTC)
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.
Worded it out. Keres🌑(talk • ctb) 00:40, 28 May 2021 (UTC)
"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..."
Changed it to "to produce...". Keres🌑(talk • ctb) 00:44, 28 May 2021 (UTC)
"minutes at room temperature", maybe "reaction times of a few minutes at room temperature"?
Done. Keres🌑(talk • ctb) 00:44, 28 May 2021 (UTC)
link "arenes"
@RoySmith: Done. Keres🌑(talk • ctb) 00:44, 28 May 2021 (UTC)


### Additional comments
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)
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.
Included all four. Keres🌑(talk • ctb) 19:09, 28 May 2021 (UTC)
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)
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)


### Next steps
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)
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)
Thanks! Keres🌑(talk • ctb) 18:31, 4 June 2021 (UTC)
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)
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)


### Second opinion needed
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)

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)
@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)

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)

 

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?
Added gold(I) chloride.
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
Removed. Keres🌕Luna edits! 17:57, 8 April 2023 (UTC)
Keres🌕, you may have missed the light decomposition commment Jimfbleak - talk to me? 11:50, 9 April 2023 (UTC)
I am still working on that, as I cannot find the decomposition products. Keres🌕Luna edits! 13:48, 9 April 2023 (UTC)
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)
Ok, I still cannot find the decomposition products. Do you have any more comments? Keres🌕Luna edits! 21:56, 13 April 2023 (UTC)
 
GA review (see here for what the criteria are, and here for what they are not)

It is reasonably well written.
a. (prose, spelling, and grammar): 

b. (MoS for lead, layout, word choice, fiction, and lists): 

It is factually accurate and verifiable.
a. (reference section): 

b. (citations to reliable sources): 

c. (OR): 

d. (copyvio and plagiarism): 

It is broad in its coverage.
a. (major aspects): 

b. (focused): 

It follows the neutral point of view policy.
Fair representation without bias: 

It is stable.
No edit wars, etc.: 

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): 

Overall:
Pass/fail: 

(Criteria marked  are unassessed)

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)

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)
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)


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

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

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