SPECIAL FEATURES OF THE NUCLEOPHILIC SUBSTITUTION OF HALOGEN IN ALKYL AND BENZYL HALIDES WITH ANIONS GENERATED FROM 4-HYDROXY-2-MERCAPTO-6-METHYLPYRIMIDINE

Authors

  • А. И. Рахимов Volgograd State Technical University, Volgograd 400131
  • Е. С. Титова Volgograd State Technical University, Volgograd 400131
  • Р. Г. Федунов Institute of Enviromental Chemical Problems, Russian Academy of Natural Sciences, Volgograd 400131
  • В. А. Бабкин Volgograd State University of Architecture, Sebyakov Branch, Mikhailovka 403330

DOI:

https://doi.org/10.1007/7093

Keywords:

2-alkyl(benzyl)thio-6-methylpyrimidin-4(3H)-one, S-, O-anions, 4-hydroxy-2-mercapto-6-methylpyrimidine, charges on atoms, quantum-chemical calculations, ab initio method, electron density

Abstract

The nucleophilic substitution of halogen (chlorine, bromine, and iodine) in alkyl and benzyl halides has been effected in aqueous dioxane media with S- and O-anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine. Under these conditions replacement of halogen proceeds by an SN2 mechanism and the reactivity of S-anions is 10 times greater than that of O-anions, which is in agreement with the results of ab initio quantum-chemical calculations of the electronic structure and total energy of transition states, carried out within the framework of the restricted Hartree-Fock method, basis 6-31G**.

How to Cite
Rakhimov, A. I.; Titova, E. S.; Fedunov, R. G.; Babkin, V. A.  Chem. Heterocycl. Compd. 2008, 44, 700. [Khim. Geterotsikl. Soedin. 2008, 874.]

For this article in the English edition see DOI 10.1007/s10593-008-0105-6


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Published

2022-09-30

Issue

No. 6 (2008)

Section

Original Papers