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Quantum-chemical study of nucleophilic substitution in protonated trisindolylmethane*

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Chemistry of Heterocyclic Compounds Aims and scope

The total energies of reactants, products, and transition states of nucleophilic substitution reactions in protonated tris(indol-3-yl)methane have been assessed with the semiempirical AM1 method and the theory of functional density B3LYP/6-31(d) method. The results of calculations indicated that the reactions proceed by an S N 1-like mechanism, since the activation barrier for it is significantly lower than in the case of the S N 2-like mechanism.

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Authors and Affiliations

  1. A. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, 119867, Russia

    E. E. Bykov, S. N. Lavrenov & M. N. Preobrazhenskaya

  2. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russia

    N. D. Chuvylkin

Authors
  1. E. E. Bykov
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  2. N. D. Chuvylkin
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  3. S. N. Lavrenov
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  4. M. N. Preobrazhenskaya
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Correspondence to E. E. Bykov.

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*Dedicated to the shining memory of A. N. Kost.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1526-1532, October, 2010.

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Bykov, E.E., Chuvylkin, N.D., Lavrenov, S.N. et al. Quantum-chemical study of nucleophilic substitution in protonated trisindolylmethane*. Chem Heterocycl Comp 46, 1233–1238 (2011). https://doi.org/10.1007/s10593-011-0657-8

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  • DOI: https://doi.org/10.1007/s10593-011-0657-8

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