Base Strengths of Cyanoamines1

GW Stevenson, D Williamson

Index: Stevenson; Williamson Journal of the American Chemical Society, 1958 , vol. 80, p. 5943,5946

Full Text: HTML

Citation Number: 35

Abstract

During the course of conversion of secondary to tertiary bases by cyanoethylation it was found that the tertiary cyanoethylamines were considerably weaker bases than the secondary amines and about 3 pK units weaker than the corresponding tertiary ethylamines. That the highly electron-withdrawing cyano group should exert a base-weakening effect was to be anticipated but its magnitude was surprising.