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Study of the electronic structure and reactivity of 4-hydroxyisoquinoline by the molecular orbital method

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reactivity indexes of the neutral, cationic, anionic, and dipolar forms of 4-hydroxyisoquinoline, calculated by the molecular orbital method using dynamic and static approximations, were compared with the experimental data on electrophilic substitution reactions in various media. Good agreement between the experimentally found orientations (3> 1>8, 7, 6, 5) and the localization energies and boundary densities was obtained. The reactivity indexes of the neutral form of 4-hydroxyisoquinoline were calculated by the Pariser-Parr-Pople method.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    B. E. Zaitsev, N. A. Andronova, V. T. Grachev, V. P. Lezina, K. M. Dyumaev & L. D. Smirnov

  2. Scientific-Research Institute of Organic Intermediates and Dyes, Moscow

    B. E. Zaitsev, N. A. Andronova, V. T. Grachev, V. P. Lezina, K. M. Dyumaev & L. D. Smirnov

Authors
  1. B. E. Zaitsev
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  2. N. A. Andronova
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  3. V. T. Grachev
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  4. V. P. Lezina
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  5. K. M. Dyumaev
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  6. L. D. Smirnov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 197–201, February, 1972.

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Zaitsev, B.E., Andronova, N.A., Grachev, V.T. et al. Study of the electronic structure and reactivity of 4-hydroxyisoquinoline by the molecular orbital method. Chem Heterocycl Compd 8, 176–179 (1972). https://doi.org/10.1007/BF00472352

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  • DOI: https://doi.org/10.1007/BF00472352

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