STRONGLY BASIC SYSTEMS: IV. SUBSTITUENT EFFECTS ON THE ACIDITY OF AROMATIC AMINES

Abstract

The effect of ring substituents on the acidity of anilines and diphenylamines is examined. In general the effects are similar to those found in the analogous ionization of phenols. The acidities of diphenylamines having two or three nitro groups in one ring and variable substituents in the other ring can be correlated by the Hammett relation.A good correlation is found between the acidities and basicities of aromatic amines, although basicity is more sensitive to the presence of ring substituents than is acidity. The relation of these results to the general question of first and second dissociation constants of dibasic acids is considered.