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Resonance and Intramolecular Configuration


A COMPARISON of the absorption spectra of I (n = 1, 2 and 3 respectively) is cited as evidence that the steric requirements of the seven-membered ring (n = 3) impose a non-planar configuration which obstructs conjugation of the nitrogen atom with the benzene ring1. We wish to make it clear that although the seven-membered ring is puckered and can allow rotation of the group Me—N—CH2— from the plane of the benzene ring, there is little reliable evidence that it enforces a rotation which effectively curtails the resonance energy which, apart from that in the benzene ring, is estimated to be 6 kcal.2.

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  4. Unpublished observations.

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BADDELEY, G., CHADWICK, J. & RAWLINSON, S. Resonance and Intramolecular Configuration. Nature 164, 833–834 (1949).

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