Abstract
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.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Rent or buy this article
Get just this article for as long as you need it
$39.95
Prices may be subject to local taxes which are calculated during checkout
References
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).
Unpublished observations.
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).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
BADDELEY, G., CHADWICK, J. & RAWLINSON, S. Resonance and Intramolecular Configuration. Nature 164, 833–834 (1949). https://doi.org/10.1038/164833a0
Issue Date:
DOI: https://doi.org/10.1038/164833a0
This article is cited by
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
