Quantum-chemical study of nucleophilic substitution in protonated trisindolylmethane

Quantum-chemical study of nucleophilic substitution in protonated trisindolylmethane

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...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2011, Vol.46 (10), p.1233-1238
Hauptverfasser: Bykov, E. E, Chuvylkin, N. D, Lavrenov, S. N, Preobrazhenskaya, M. N
Format: Artikel
Sprache:eng
Schlagworte:
B3LYP/6-31G(d)
Chemistry
Chemistry and Materials Science
Methane
methods AM1
nucleophilic substitution
Organic Chemistry
Pharmacy
quantum-chemical calculations
Substitution reactions
trisindolylmethane
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Zusammenfassung: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-011-0657-8