Configurational prevalence at the nitrogen atom in chiral, open chain, secondary amines

Abstract

The stereochemistry of chiral, open chain, secondary amines has been studied by means of low-temperature ¹H and ¹³C n.m.r. spectroscopy and by PCILO molecular-orbital calculations. The chiral nitrogen assumes a strongly prevalent configuration under the asymmetric induction of a vicinal asymmetric carbon atom. In the most probable conformation of the secondary amine the lone pair of the nitrogen is placed in the most crowded position.