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This is a simple vocabulary question. Is there a single chemical term in general use that generalizes the concept of "benzyl" to aromatic but not necessarily benzene rings?

For example, in the case of phenyl or benzene rings, people talk about "benzylamine", the "benzylic position", "benzyl bromide", etc.

To be more general about aromatic rings, people talk about "arenes", and this would include not just benzene rings like in toluene or naphthalene, but also aromatic rings like pyrroles, isoxazoles, thiophenes, furans, pyridines, etc.

So what is the "benzylic position" of a general aromatic ring called? Is there a more general term for the "benzylic" position in compounds like 3-aminomethylpyridine, furfuryl alcohol, 3-hydroxymethylpyrrole? Can I still call it "benzylic"? Or is there a different word?

(Note: I'm not really interested in an official IUPAC-designated term here, unless that term also happens to be in general use in the chemical community.)

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    $\begingroup$ Well, it's not benzylic... couldn't it be just called an alpha position respective the ring? $\endgroup$
    – Mithoron
    Commented Nov 1, 2022 at 21:41
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    $\begingroup$ Since the rings involved are annulenes, "annulylic" maybe? $\endgroup$ Commented Nov 1, 2022 at 22:00
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    $\begingroup$ @OscarLanzi "Annulyl" would be rather an aromatic group connected directly like phenyl not benzyl. There's for eg. furyl, tolyl, etc. but they're aryl not arylmethyl groups like benzyl. $\endgroup$
    – Mithoron
    Commented Nov 1, 2022 at 22:31
  • $\begingroup$ @Mithoron Maybe I just need the word "arylmethyl"? $\endgroup$
    – Curt F.
    Commented Nov 1, 2022 at 22:33
  • $\begingroup$ books.google.com/ngrams/graph?content=arylmethyl $\endgroup$
    – Curt F.
    Commented Nov 1, 2022 at 22:35

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It appears that aryl methyl is occasionally used. For example, there are references to aryl methyl ketones, which is basically a benzylic ketone if a benzene group is involved [1][2].

However, this 'aryl methyl' reference can also refer to the nomenclature of ethers and sulfides (i.e. aryl methyl ether)

Sources:

[1] https://cen.acs.org/articles/92/i4/Simple-Method-Aryl-Methyl-Ketones.html

[2] https://pubs.acs.org/doi/full/10.1021/jo062483g

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  • $\begingroup$ Do you prefer "aryl methyl" with a space, or "arylmethyl" with no space? $\endgroup$
    – Curt F.
    Commented Nov 3, 2022 at 15:56
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    $\begingroup$ I would personally prefer aryl methyl for clarity, but it isn't really something I can say as a fact. It isn't a very widely used term, I only found several references to it in published works. $\endgroup$
    – M.L
    Commented Nov 4, 2022 at 6:07

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