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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Remington, J. Amer. Chem. Soc., 67, 1838 (1945).
Pauling, "Nature of the Chemical Bond", 139 (Cornell, 2nd edit. 1940).
Ramart-Lucas and Hoch, Bull. Soc. Chim., (5), 2, 327 (1935). Bicquard, Bull. Soc. Chim., (5), 8, 55 (1941).
Morton and de Gouveia, J. Chem. Soc., 911, 916 (1934).
Brown, Widiger and Letang, J. Amer. Chem. Soc., 61, 2597(1939).
Wheland, "The Theory of Resonance", 235 (1947).
Berliner and Berliner, J. Amer. Chem. Soc., 71, 1195 (1949).
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BADDELEY, G., CHADWICK, J. & RAWLINSON, S. Resonance and Intramolecular Configuration. Nature 164, 833–834 (1949). https://doi.org/10.1038/164833a0
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