AM1 study of the chiral stabilities of ketenimines

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.