QUANTUM-CHEMICAL STUDY OF NUCLEOPHILIC SUBSTITUTION IN PROTONATED TRISINDOLYLMETHANE

Authors

  • Е. Е. Быков A. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow 119867
  • Н. Д. Чувылкин D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991
  • С. Н. Лавренов A. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow 119867
  • М. Н. Преображенская A. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow 119867

DOI:

https://doi.org/10.1007/5251

Keywords:

trisindolylmethane, quantum-chemical calculations, methods AM1, B3LYP/6-31G(d), nucleophilic substitution.

Abstract

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 SN1-like mechanism, since the activation barrier for it is significantly lower
than in the case of the SN2-like mechanism.

How to Cite
Bykov, E. E.; Chuvylkin, N. D.;Lavrenov, S. N.; Preobrazhenskaya, M. N.  Chem. Heterocycl. Compd. 2011, 46, 1233. [Khim. Geterotsikl. Soedin. 2010, 1526.]

For this article in the English edition see DOI 10.1007/s10593-011-0657-8



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Published

2019-07-08

Issue

No. 10 (2010)

Section

Original Papers