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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

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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;α=105.56(3),β=113.50(4), γ=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 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 theN-methyl acetanilide moiety and its relation to the1H NMR spectrum of the compound are discussed.

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Chakrabarti, P., Venkatesan, K., Stanley Cameron, T. et al. 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. Journal of Crystallographic and Spectroscopic Research 15, 229–245 (1985). https://doi.org/10.1007/BF01160483

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  • DOI: https://doi.org/10.1007/BF01160483

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