Steric effects on mesomerism IX : The basic strength of benzoquinuclidine and its bearing on the basic strength and the mesomeric energy of aromatic amines

Abstract

In this paper it is shown that the low basic strength of aromatic amines as compared with aliphatic amines is equally due to the inductive and the mesomeric effect; each of these is responsible for a decrease of about three pKa units. On this basis the (extra) mesomeric energy of aromatic amines is calculated as 4 kcal/mol.