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This article was the subject of a Wiki Education Foundation-supported course assignment, between 9 January 2023 and 28 April 2023. Further details are available on the course page. Student editor(s): Doodlepuppy123 (article contribs). Peer reviewers: CorrelationSpec.

— Assignment last updated by RS UBC800 (talk) 21:15, 2 April 2023 (UTC)[reply]

The entire “properties” section of the Wikipedia article does not have sources. More reliable references need to be provided for each claim. There is an image of the cyclopentadienyl anion as a pentagon with a circle inside and a charge inside of that. However, I would like to add images of the 5 resonance structures that show why there is a “circle” inside (because all are equivalent and just show how the lone pair can be moved around). I think that many people in the general public may not know what a circle inside a cyclic structure means, so I would like to simplify/clarify a bit. I would like to add more information to the “properties” section of the article and I will add more sources that back up the current information and any new information that I add. I plan on adding more information about its characteristics as a ligand.

Doodlepuppy123 (talk) 19:36, 11 March 2023 (UTC)[reply]

I suggest the "This article needs additional citations for verification" flag can now be removed. RS UBC800 (talk) 18:37, 26 April 2023 (UTC)[reply]

This proposal might be controversial, which I am cool with.

Current situation

• Sodium cyclopentadienide, a real compound with a rich chemistry. Notable for sure.
• Cyclopentadienyl cation, super rarely observed and never invoked. The cation is mentioned once in March as one of several examples of an antiaromatic system. This article is a redirected to Antiaromaticity. Ok.
• Cyclopentadienyl radical, super rarely observed and never invoked. Not notable. The radical is not mentioned in March (sort of a bible of organic chem). Unlinked within Wikipedia except List of compounds with carbon number 5 and a disambiguation page.
• Cyclopentadienyl anion, often invoked but mistakenly (to a purist). It is always bonded to a cation. If one were to measure the ionic conductivity of a NaCp solution, the result would be nil. By having this article, we risk propagating myths. (we do not have a phenyl anion, but we do have phenyl lithium)
• Cyclopentadienyl is a disambiguation to the preceding three (nonexistent things).

• Proposal 0: The situation is slightly messy, but leave it alone.
• Proposal 1: Merge Cyclopentadienyl radical + Cyclopentadienyl anion into Cyclopentadienyl, which will no longer be a disambiguation.
• Proposal 2: Merge Cyclopentadienyl radical + Cyclopentadienyl anion into Sodium cyclopentadienide.

--Smokefoot (talk) 01:03, 11 November 2024 (UTC)[reply]

Support Proposal 1. There is already an example of this, methyl. Nucleus hydro elemon (talk) 07:06, 11 November 2024 (UTC)[reply]

I don't have a preference between status-quo and Proposal 1 but believe Proposal 2 would lead to a too bulky a wide-scope article. Also I would like to note that unlike Trifluoromethyl cation and Trifluoromethyl group cyclopentadienyl articles have interwikis, and unlike Acylium ions, more than one (cf. Acyl group). 5.178.188.143 (talk) 07:53, 11 November 2024 (UTC)[reply]

I had not considered the interwiki issue. Interwiki = links to a related article in another language? I have just proposed that Trifluoromethyl cation be merged into Trifluoromethylation. I do not know what you are proposing with regard to acylium vs acyl.--Smokefoot (talk) 16:20, 11 November 2024 (UTC)[reply]