Russian Chemical Bulletin

, Volume 46, Issue 11, pp 1838–1843

Molecular structure and conformation flexibility of 2-oxo- and 2-thioxo-1,2,3,4-tetrahydropyrimidines and their derivatives

Authors

  • O. V. Shishkin
    • A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of Sciences
  • E. V. Solomovich
    • A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of Sciences
  • V. M. Vakula
    • Ukrainian Institute of Pharmacotherapy of Endocrynologic Deseases
  • F. G. Yaremenko
    • Ukrainian Institute of Pharmacotherapy of Endocrynologic Deseases
Physical Chemistry

DOI: 10.1007/BF02503768

Cite this article as:
Shishkin, O.V., Solomovich, E.V., Vakula, V.M. et al. Russ Chem Bull (1997) 46: 1838. doi:10.1007/BF02503768

Abstract

The conformational flexibility and effects of the substituents in 2-oxo- and 2-thioxo-1,2,3,4-tetrahydropyrimidines were studied by the semiempirical quantum-chemical AM1 method. The substituents at the double bond have no appreciable effect on the conformational characteristics of the heterocycle. The introduction of substituents to the saturated carbon atom results in the conversion of the tetrahydrocycle to a half-chair conformation and in a substantial decrease in the ring flexibility. The results of calculations are confirmed by the X-ray study of both compounds.

Key words

2-oxo-1,2,3,4-tetrahydropyrimidine2-thioxo-1,2,3,4-tetrahydropyrimidineconformational analysisAM1molecular structureX-ray study

Copyright information

© Plenum Publishing Corporation 1997