Aromatic amines and their derivatives, Part 2. Synthesis, spectroscopic properties, and molecular and crystal structure of N-acetyl-4,N-dimethyl-6-(N-acetyl-p-toluidinomethyl)aniline

Abstract

The synthesis and selected aspects of the UV, IR, and ¹H NMR spectra of the title compound are described. The crystals of the title compound are triclinic with a=12.999(9), b=8.911(4), c=9.199(5) Å; α= 105.56(3), β= 113.50(4), γ=92.53(3)°; Z = 2; space group P-1. Its X-ray crystal structure analysis provides information regarding the conformational features of the amide linkage when no intermolecular hydrogen bonding involving this group is present. The X-ray study shows that the C'-N bond is longer [1.363(4) Å] than that found normally in peptide molecules. The compound shows a peculiar disorder involving one of the two amide groups present in the molecule. The conformation of the N-methyl acetanilide moiety and its relation to the ¹H NMR spectrum of the compound are discussed.