Chemistry of Heterocyclic Compounds

, Volume 3, Issue 2, pp 604–606 | Cite as

Electronic structures and dipole moments of 4- and 5-phenyl-1, 2-dithiol-3-thiones

  • M. G. Voronkov
  • V. I. Minkin
  • O. A. Osipov
  • M. G. Kogan
  • T. V. Lapina
Brief Communications
  • 33 Downloads

Abstract

The simple LCAO MO method is used to calculate π-electron configurations of 1,2-dithiol-3-thione and its 4- and 5-phenyl derivatives. In these compounds the heterocyclic ring has an aromatic character, but the S-S bond is almost excluded from conjugation. The phenyl group in 4-phenyl-1,2-dithiol-3-thione is an electron acceptor, whereas in the 5 isomer it is an electron donor. The exocyclic sulfur atom has considerable negative charge, while the two endocyclic ones are positively charged. The dipole moments of 4- and 5-phenyl-1,2-dithiol-3-thione are determined, and the values found are compared with the calculated ones.

Keywords

Dipole Moment Carbazole Heterocyclic Ring Yellow Amorphous Powder Aromatic Nature 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. G. Voronkov, Study of the reaction of sulfur with phenylolefins [in Russian], Master's thesis, LGU, Leningrad, 1947.Google Scholar
  2. 2.
    F. Baner, Chem. Ztg., 75, 623, 1951.Google Scholar
  3. 3.
    L. Jirousek, Chem. Listy, 53, 501, 1959.Google Scholar
  4. 4.
    E. E. Reid, Organic Chemistry of Bivalent Sulfur, Vol. III, N. Y., 43, 1960.Google Scholar
  5. 5.
    N. Lozach, Ind. Chim. Belge, 26, 1130, 1961.Google Scholar
  6. 6.
    P. S. Landis, Chem. Rev., 65, 237, 1958.CrossRefGoogle Scholar
  7. 7.
    W. L. Kehl and G. A. Jeffrey, Acta Cryst., 11, 813, 1958.CrossRefGoogle Scholar
  8. 8.
    A. Hordvik, Acta Chem. Scand., 17, 1809, 1963.Google Scholar
  9. 9.
    Tables of Interatomic Distances and Configuration in Molecules and Ions, London, 1958.Google Scholar
  10. 10.
    G. Bergson, Arh. Kemi, 19, 181, 1962.Google Scholar
  11. 11.
    R. Zahradnik, Adv. Heterocycl. Chem., 5, 1, 1965.Google Scholar
  12. 12.
    M. J. Jannsem and J. Sandstrom, Tetrahedr., 20, 2339, 1964.CrossRefGoogle Scholar
  13. 13.
    L. Orgel, T. L. Cottrell, V. Dich, and L. E. Sutton, Trans. Fard. Soc., 47, 113, 1951.CrossRefGoogle Scholar
  14. 14.
    M. G. Voronkov and T. V. Lapina, KhGS [Chemistry of Heterocyclic Compounds], 342, 1965.Google Scholar
  15. 15.
    M. G. Voronkov and T. H. Lapina, KhGS, [Chemistry of Heterocyclic Compounds], 522, 1966.Google Scholar
  16. 16.
    O. A. Osipov, ZhOKh, 26, 322, 1965.Google Scholar
  17. 17.
    Yu. A. Ostroumov, Program for Computing Molecules by the Hückel MO Method [in Russian], Izd. RGU, Rostov-on-Don, 1965.Google Scholar

Copyright information

© The Faraday Press, Inc. 1969

Authors and Affiliations

  • M. G. Voronkov
    • 1
  • V. I. Minkin
    • 1
  • O. A. Osipov
    • 1
  • M. G. Kogan
    • 1
  • T. V. Lapina
    • 1
  1. 1.Institute of Organic Synthesis AS Latvian SSRRostov-on-Don State UniversityRiga

Personalised recommendations