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So I've been trying to understand what exactly aromaticity means, and I've come to know that compounds possessing benzene rings are aromatic, like toluene and phenol. It thus made sense to me that the benzylic carbocation should be aromatic, as it fulfills all conditions of Huckel's rule. However, I found no mention of it being aromatic anywhere. Can anyone tell me if it is indeed aromatic or is only resonance stabilised, and if it is not aromatic, why so? What criteria is it violating?

Sorry if this is an elementary question, I really want to know what aromaticity actually means and am stuck on this.

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    $\begingroup$ For this case, aromaticity is most easily understood when comparing the stability to other carbocations. That being said, you'll find that aromaticity, much like a chemical bond, is like a unicorn: everyone knows what it should look like, nobody has ever really observed one or can give a quantitative measure except in a few narrow cases. $\endgroup$ – TAR86 Mar 12 '20 at 6:29
  • $\begingroup$ Basic criteria is a cyclic molecule with 4n+2 pi electrons, as described in most undergraduate courses on physical organic chemistry $\endgroup$ – Beerhunter Apr 16 '20 at 13:45
  • $\begingroup$ Sorry, forgot to mention that an alternative form of the benzyl cation is the cycloheptatrienyl cation. Hopefully that helps. $\endgroup$ – Beerhunter Apr 16 '20 at 13:48

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