J. Clayden et al., Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides, CHEM COMMUN, (20), 1999, pp. 2059-2060
8-Substituted tertiary 1-naphthamides are chiral, atropisomeric compounds a
t room temperature, and the rate at which they racemise (by rotation about
the Ar-CO bond) depends principally on the extent to which the 8-substituen
t undergoes incipient nucleophilic addition to the amide carbonyl group, as
indicated by X-ray crystallography.