AM1 Study of the Chiral Stabilities of Ketenimines†

Abstract

AM1 Semi-empirical SCF MO calculations are used to investigate the configurational racemization energies and structural properties of ketenimines 1a–r; these calculations show that stereoisomerization proceeds through nitrogen atom inversion and rotation around the C–C or C–N bond, and that it requires about 40 to 60 kJ mol ^–1 more energy than nitrogen inversion alone.