Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides†

Abstract

8-Substituted tertiary 1-naphthamides are chiral, atropisomeric compounds at 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-substituent undergoes incipient nucleophilic addition to the amide carbonyl group, as indicated by X-ray crystallography.