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Hindered internal rotation about the C-N partially double bond in N-acyl derivatives of 1,2,3,4-tetrahydroquinoline

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The inhibited internal rotation about the C-N partially double bond in N-acyl-1,2,3,4-tetrahydroquinolines was investigated by NMR spectroscopy. It is demonstrated that these compounds exist in the form of Z and E conformers, and their ratios are determined under the conditions of stereochemical rigidity. The activation parameters of internal rotation about the C-N bond, specifically the barrier to rotation, as a function of the form·of the acyl grouping were calculated.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    L. B. Krivdin, V. N. Torocheshnikov, N. M. Sergeev, I. G. Il'ina & N. B. Kazennova

Authors
  1. L. B. Krivdin
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  2. V. N. Torocheshnikov
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  3. N. M. Sergeev
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  4. I. G. Il'ina
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  5. N. B. Kazennova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1092–1096, August, 1980.

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Krivdin, L.B., Torocheshnikov, V.N., Sergeev, N.M. et al. Hindered internal rotation about the C-N partially double bond in N-acyl derivatives of 1,2,3,4-tetrahydroquinoline. Chem Heterocycl Compd 16, 849–853 (1980). https://doi.org/10.1007/BF00513169

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  • DOI: https://doi.org/10.1007/BF00513169

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