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New method for allowance for the activity of the nucleophile in calculations of the reactivities of heteroaromatic compounds

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A new method for allowance for the activity of the nucleophile in calculations of the reactivities of heteroaromatic compounds that is based on the special application of the valence molecular orbital (VMO) theory in the form of Dewar reactivity numbers is proposed. It is shown that there is a correspondence between the proposed method and the general VMO theory. The 5-azacinnoline molecule was calculated by both methods. According to the calculations, the 6-C atom should be the most active in reactions with hard bases, whereas the 4-C atom should be the most active in reactions with soft bases. A qualitative correspondence between the proposed method and the DMTS (delocalization model of the transition state) method is also demonstrated in the case of the quinolinium cation.

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Authors and Affiliations

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

    M. F. Budyka & P. B. Terent'ev

Authors
  1. M. F. Budyka
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  2. P. B. Terent'ev
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Additional information

More complex computational methods are presently not applicable to many-atom systems and not found in the literature.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 403–405, March, 1979.

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Budyka, M.F., Terent'ev, P.B. New method for allowance for the activity of the nucleophile in calculations of the reactivities of heteroaromatic compounds. Chem Heterocycl Compd 15, 333–335 (1979). https://doi.org/10.1007/BF00474104

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  • DOI: https://doi.org/10.1007/BF00474104

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