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Aromatic amines and their derivatives,Part 2. Synthesis,spectroscopic properties,and molecular and crystal structure ofN-acetyl-4,N-dimethyl-6-(N-acetyl-p-toluidinomethyl)aniline
Authors:Pinakpani Chakrabarti  Kailasam Venkatesan  T Stanley Cameron  Türsen Demir  Robert A Shaw
Institution:(1) Department of Organic Chemistry, Indian Institute of Science, 560012 Bangalore, India;(2) Department of Chemistry, Dalhousie University, B3H 4J3 Halifax, Canada;(3) Department of Chemistry, Birkbeck College (University of London), Malet Street, WC1E 7HX London, UK
Abstract:The synthesis and selected aspects of the UV, IR, and1H NMR spectra of the title compound are described. The crystals of the title compound are triclinic witha=12.999(9),b=8.911(4),c=9.199(5) Å;agr=105.56(3),beta=113.50(4), gamma=92.53(3)°;Z=2; space groupP¯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 Cprime-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 theN-methyl acetanilide moiety and its relation to the1H NMR spectrum of the compound are discussed.
Keywords:
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