Advertisement

Chemistry of Heterocyclic Compounds

, Volume 20, Issue 12, pp 1348–1353 | Cite as

Molecular and crystal structure of 2-para-toluimido-4,4-dimethyl-(4H)-1,3-thiazine

  • L. G. Kuz'mina
  • A. A. Espenbetov
  • Yu. T. Struchkov
  • S. T. Cholpankulova
  • L. A. Tsoi
Article
  • 23 Downloads

Abstract

The imino structure of 2-p-toluimido-4,4-dimethyl-(4H)-1,3-thiazine (I) was demonstrated by x-ray diffraction structural analysis. Molecules of I in the crystal are linked by N-H⋯O hydrogen bonds in infinite chains. A shortened S⋯O intramolecular contact was found which corresponds to a secondary interaction. A mechanism was proposed for the thiazoline-thiazine rearrangement.

Keywords

Hydrogen Crystal Structure Hydrogen Bond Organic Chemistry Dimethyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    I. N. Azerbaev, L. A. Tsoi, A. D. Salimbaeva, S. T. Cholpankulova, G. A. Ryskieva, L. T. Kalkabaeva, and M. Zh. Aitkhozhaeva, Trudy Inst. Khim. Nauk KazSSR (Alma-Ata), 52, 128 (1980).Google Scholar
  2. 2.
    L. A. Tsoi, L. T. Kalkabaeva, S. T. Cholpankulova, G. A. Ryskieva, and A. D. Salimbaeva, Izv. Akad. Nauk KazSSR, Ser. Khim., No. 5, 73 (1980).Google Scholar
  3. 3.
    A. Kalman, G. Argay, B. Ribar, and L. Toldy, Tetrahedron Lett., No. 48, 4241 (1977).Google Scholar
  4. 4.
    B. Tashkhodzhaev, S. Akhmedov, and N. K. Rozhkova, Zh. Skrukt. Khim., 21, 137 (1980).Google Scholar
  5. 5.
    A. Kálmán, G. Argay, and I. Vassányi, Tetrahedron Lett., No. 48, 4237 (1977).Google Scholar
  6. 6.
    S. Sólyom, P. Sohár, L. Toldy, A. Kálmán, and L. Párkányi, Tetrahedron Lett., 48, 4245 (1977).Google Scholar
  7. 7.
    M. Mammi, R. Bardi, G. Traverse, and S. Bezzi, Nature, 192, 1282 (1961).Google Scholar
  8. 8.
    S. Bezzi, M. Mammi, and C. Garbuglio, Nature, 182, 247 (1958).Google Scholar
  9. 9.
    F. Leung and S. C. Nyburg, Chem. Commun., No. 4, 137 (1969).Google Scholar
  10. 10.
    A. Hordvik and H. M. Kjoge, Acta Chem. Scand., 20, 1923 (1966).Google Scholar
  11. 11.
    T. R. Lynch, I. P. Mellor, and S. C. Nyburg, Acta Crystallogr., B27, 1948 (1971).Google Scholar
  12. 12.
    A. Bondi, J. Phys. Chem., 68, 441 (1964).Google Scholar
  13. 13.
    I. P. Mellor and S. C. Nyburg, Acta Crystallogr., B27, 1954 (1971).Google Scholar
  14. 14.
    S. Stanković, B. Ribár, A. Kálmán, and G. Argay, Acta Crystallogr., B36, 1235 (1980).Google Scholar
  15. 15.
    C. Cohen-Addad, J. M. Sovariault, and M. S. Lehmann, Acta Crystallogr., B37, 1703 (1981).Google Scholar
  16. 16.
    A. Atkinson, A. G. Brewster, S. V. Ley, R. S. Osborn, D. Rogers, D. Williams, and K. Woode, Chem. Commun., No. 9, 325 (1977).Google Scholar
  17. 17.
    A. Gieren and B. Dederer, Acta Crystallogr., B34, 2046 (1978).Google Scholar
  18. 18.
    I. P. Mellor and S. C. Nyburg, Acta Crystallogr., B27, 1959 (1971).Google Scholar
  19. 19.
    J. Sletten and M. Velsvik, Acta Chem. Scand., 27, 3881 (1973).Google Scholar
  20. 20.
    R. Pinel, Y. Mollier, E. C. Llaguno, and I. C. Paul, Chem. Commun., No. 21, 1352 (1971).Google Scholar
  21. 21.
    B. Dahlén, Acta Crystallogr., B29, 595 (1973).Google Scholar
  22. 22.
    J. D. Korp, I. Bernal, and G. E. Martin, Cryst. Mol. Struct., 11, 11 (1981).Google Scholar
  23. 23.
    J. D. Korp, I. Bernal, R. F. Miller, J. C. Turley, L. Williams, and G. E. Martin, J. Cryst. Mol. Struct., 8, 127 (1978).Google Scholar
  24. 24.
    W. C. Hamilton and S. J. La Placa, J. Amer. Chem. Soc., 86, 2289 (1964).Google Scholar
  25. 25.
    P. L. Johnson and I. C. Paul, J. Amer. Chem. Soc., 91, 781 (1969).Google Scholar
  26. 26.
    W. E. Sutton (editor), Tables of Interatomic Distances and Configuration in Molecules and Ions, Special Publication No. 18, Chemical Society, Oxford Press, London (1965).Google Scholar
  27. 27.
    N. D. Epiotis, W. R. Cherry, S. Shaik, R. L. Yates, and F. Bernardi, Structural Theory of Organic Chemistry, Topics in Current Chemistry 70, Springer-Verlag, Berlin-Heidelberg-New York (1977).Google Scholar
  28. 28.
    V. I. Minkin, L. P. Olekhnovich, and Yu. A. Zhdanov, The Molecular Design of Tautomeric Systems [in Russian], Izd. Rostovsk. Univ., Rostov-on-the-Don (1977), p. 232.Google Scholar
  29. 29.
    L. G. Kuz'mina, Yu. T. Struchkov, D. N. Kravtsov, and L. S. Golovchenko, Zh. Strukt. Khim., 23, 102 (1982).Google Scholar
  30. 30.
    N. G. Furmanova, Usp. Khim., 50, 1491 (1981).Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • L. G. Kuz'mina
    • 1
    • 2
  • A. A. Espenbetov
    • 1
    • 2
  • Yu. T. Struchkov
    • 1
    • 2
  • S. T. Cholpankulova
    • 1
    • 2
  • L. A. Tsoi
    • 1
    • 2
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow
  2. 2.Institute of Chemical SciencesAcademy of Sciences of the Kazakh SSRAlma-Ata

Personalised recommendations