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Influence of Z,E-isomerism on the chiral-optical properties of amides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The study of the chiral-optical properties of N-acyl-(−)-1-methyl-1,2,3,4-tetrahydroisoquinolines and their acyclic analogs, the n-acyl-(−)-1-phenylethylamines, with the known ratio of Z- and E-isomers showed that the Z-isomers are characterized by the negative Cotton effect in the region of the absorption band of the amide chromophore. The observed Cotton effects of amides of phenylethylamine, which are higher by comparison with those of amides of tetrahydroisoquinoline, are explained by the interaction of the amide and aromatic chromophores, which are in proximity in certain conformation, possible for acyclic conformationally free phenylethylamides.

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Authors
  1. V. M. Dem'yanovich
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  2. I. N. Shishkina
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Additional information

Chemical Faculty, M. V. Lomonosov Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 944–949, July, 1996. Original article submitted May 23, 1996.

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Dem'yanovich, V.M., Shishkina, I.N. Influence of Z,E-isomerism on the chiral-optical properties of amides. Chem Heterocycl Compd 32, 807–811 (1996). https://doi.org/10.1007/BF01165725

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  • DOI: https://doi.org/10.1007/BF01165725

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