Aromatic amides. xi: 1, 3- Phenylenediamines and their diacyl derivatives

Abstract

In 4, 6-disubstituted N, N′-(1, 3-phenylene)bispivalamides, the ring hydrogen between the two amide groups is deshielded by both and consequently shows its 1H nuclear magnetic resonance at extremely low field. Preferential stabilization of a particular amide configuration by dipole-dipole interactions gives rise to differential shielding effects in N, N′-(4-chloro-1, 3-phenylene)bispivalamide and to strong deshielding of the aromatic C5-H in N, N′-(2-methylthiopyrimidine-4, 6-diyl)bispival amide. © 1978 Australian Journal of Chemistry.