Compare the resonance energies of indole (a) and isoindole (b). Is the resonance energy of (a) greater than, less than or equal to that of (b) ?
(a) (b)

Question

Compare the resonance energies of indole (a) and isoindole (b). Is the resonance energy of (a) greater than, less than or equal to that of (b) ? (a) (b)

TestHub · Accepted Answer

In indole both rings keep a full cyclic conjugation (10π). In isoindole the benzene ring is forced into an o-quinoid form, which costs much of its aromatic stabilisation. So a > b.

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