Derivatives of m-di-t-butylbenzene. Part 8. Dissociation constants of 2-halogeno-4,6-di-t-butylanilines, and 1H nuclear magnetic resonance spectra of the corresponding acetanilides

Abstract

The dissociation constants of 2-halogeno-4,6-di-t-butylanilines have been compared with those of 2-halogenoanilines. The base-weakening effect of the t-butyl group ortho to the amino group is greatly reduced by the presence of the ortho halogen atom. The ¹H n.m.r. spectra of 2′-halogeno-4′,6′-di-t-butylacetanilides show the presence of geometrical isomers as a result of restricted rotation around the bond between the nitrogen atom and the acetyl group.