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Conformational investigation of α-methylthio and α-phenylthio derivatives of acetone and cyclohexanone by molecular mechanics. An x-ray study of α-phenylthioacetone

  • É. Kh. Kazakova
  • G. R. Davletshina
  • O. N. Kataeva
  • I. A. Litvinov
  • S. G. Vul'fson
Physical Chemistry Structure And Physicochemical Properties Of Molecules
  • 16 Downloads

Abstract

A conformational investigation of α-methylthioacetone, α-methylthiocyclohexanone, α-phenylthioacetone, and α-phenylthiocyclohexanone was undertaken in the MM2(87) force field. In all cases theac-G rotamers with unidirectional orientation of the C=O and S-R bonds are preferred in accordance with the experimental investigations. In all cases the energy of dipole-dipole interaction makes a contribution to the stabilization of these forms. For the eclipsedsp conformers the relatively high calculated values of the energies contradict the data of the experimental investigations, which take account of their participation in the equilibrium. X-ray crystallographic analysis of α-phenylthioacetone (3) showed that thesp-T structure with a planar orientation of the thioanisole fragment is realized in the solid phase.

Keywords

Methyl- and phenylthioacetones methyl and phenylthiocyclohexanones conformational investigation MM2(87) molecular mechanics method x-ray crystallographic analysis 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • É. Kh. Kazakova
  • G. R. Davletshina
  • O. N. Kataeva
  • I. A. Litvinov
  • S. G. Vul'fson

There are no affiliations available

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