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If benzene were to donate a hydrogen ion, then could the negative charge still be delocalised around the ring? Wouldn't that break aromaticity and thus destabilise the molecule?

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See: Relative acidities of alkanes, alkenes, and alkynes. Essentially the same explanation holds here, as benzene carbons are sp2-hybridised.

The newly formed lone pair is in a σ-type orbital (blue) which does not overlap with the π system (red), hence no delocalisation is possible.

Sigma and pi systems of benzene

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