99325-91-4Relevant articles and documents
Conformation and Stereodynamics of N,N-Dialkylbenzamides; a 1H and 13C Nuclear Magnetic Resonance Investigation of para-Substituted 4-Benzoyl-cis-2,6-dimethylmorpholines
Jennings, W. Brian,Saket, Barahman Movassagh
, p. 1005 - 1010 (2007/10/02)
A high-field 13C n.m.r. study of the title compounds below -80 deg C has enabled measurement of the barriers to rotation around the aryl-C(O) bond.These barriers (ΔG(excit.) 7.7-9.5 kcal mol-1), and those for rotation around the C(O)-N bond (ΔG(excit.) 13.6-15.6 kcal mol-1) determined by 1H n.m.r. at higher temperatures, correlate well with Hammett ?+ substituent parameters.The ground-state conformation has the phenyl ring twisted out of the amide plane.Some 1H and 13C chemical shift correlations are also reported.