Russian Journal of Coordination Chemistry

, Volume 29, Issue 2, pp 142–150 | Cite as

Structural Organization of Symmetrical Dialkylthiuram Disulfides and Their Cyclic Analogs: X-Ray Diffraction and CP/MAS (13C, 15N) NMR Studies

  • A. V. Ivanov
  • S. A. Zinkin
  • W. Forzling
  • O. N. Antzutkin
  • M. Kritikos
Article

Abstract

High-resolution 13C and 15N solid-state NMR spectra were recorded for seven crystalline tetraalkyl-thiuram disulfides and their cyclic analogs of the general formula [R2NC(S)S]2 (where R = CH3, C2H5, C3H7, and i-C3H7 or R2 = (CH2)5, (CH2)6, and (CH2)4O). The 15N and 13C NMR resonances were assigned to the particular atoms in the compounds studied. Different isotropic 15N chemical shifts for both dialkyldithiocarbamato groups were interpreted while considering the inductive effects of the alkyl substituents combined with the mesomeric effect of the dithiocarbamato group. X-ray diffraction data were used to refine the molecular structure of bis(cyclohexamethylene)thiuram disulfide and to quantitatively characterize the conformations of the seven-membered N(CH2)6 heterocycles.

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References

  1. 1.
    Byr'ko, V.M., Ditiokarbamaty (Dithiocarbamates), Moscow: Nauka, 1984.Google Scholar
  2. 2.
    Golding, R.M. and Tennant, W.C., Mol. Phys., 1972, vol. 24, no. 2, p. 301.Google Scholar
  3. 3.
    Jian, F.-F., Wang, Z.-X., Chen., W., et al., Polyhedron, 1999, vol. 18, no. 16, p. 2219.Google Scholar
  4. 4.
    USSR Inventor's Certificate no. 1381387, Byull. Izobret., 1988, no 10.Google Scholar
  5. 5.
    Maroy, K., Acta Chem. Scand., 1965, vol. 19, no. 6, p. 1509.Google Scholar
  6. 6.
    Ymen, I., Acta Chem. Scand., 1983, vol. 37, no. 8, p. 707.Google Scholar
  7. 7.
    Yu Wang and Liao, J.-H., Acta Crystallogr., Sect. B: Struct. Sci., 1989, vol. 45, no. 1, p. 65.Google Scholar
  8. 8.
    Karle, I.L., Estlin, J.A., and Britts, K., Acta Crystallogr., 1967, vol. 22, no. 2, p. 273.Google Scholar
  9. 9.
    Yu Wang, Liao, J.-H., and Ueng, C.-H., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1986, vol. 42, no. 10, p. 1420.Google Scholar
  10. 10.
    Jian, F.-F., Jiang, L., Fun, H.-K., et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1999, vol. 55, no. 4, p. 573.Google Scholar
  11. 11.
    Kumar, V., Aravamudan, G., and Seshasayee, M., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1990, vol. 46, no. 5, p. 674.Google Scholar
  12. 12.
    Dix, M.F. and Rae, A.D., Cryst. Struct. Commun., 1973, vol. 2, no. 1, p. 159.Google Scholar
  13. 13.
    Polyakova, I.N. and Starikova, Z.A., Zh. Strukt. Khim., 1990, vol. 31, no. 1, p. 148.Google Scholar
  14. 14.
    Rout, G.C., Seshasayee, M., and Aravamudan, G., Cryst. Struct. Commun., 1982, vol. 11, no. 4/A, p. 1389.Google Scholar
  15. 15.
    Yamin, B.M., Suwandi, S.A., Fun, H.-K., et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1996, vol. 52, no. 4, p. 951.Google Scholar
  16. 16.
    Colapietro, M., Domenicano, A., and Vaciago, A., Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1976, vol. 32, p. 2581.Google Scholar
  17. 17.
    Husebye, S., Acta Chem. Scand., 1973, vol. 27, no. 3, p. 756.Google Scholar
  18. 18.
    Jian, F.-F., Zhu, D., Fun, H.-K., et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1999, vol. 55, p. 940.Google Scholar
  19. 19.
    Pines, A., Gibby, M.G., and Waugh, J.S., J. Chem. Phys., 1972, vol. 56, no. 4, p. 1776.Google Scholar
  20. 20.
    Earl, W.L. and van der Hart, D.L., J. Magn. Res., 1982, vol. 48, no. 1, p 35.Google Scholar
  21. 21.
    Ratcliffe, C.I., Ripmeester, J.A., and Tse, J.S., Chem. Phys. Lett., 1983, vol. 99, no. 2, p. 177.Google Scholar
  22. 22.
    Mason, J., Encyclopedia of Nuclear Magnetic Resonance, vol. 5, Grant, D.M. and Harris, R.K., Eds., New York: Wiley, 1996, p. 3222.Google Scholar
  23. 23.
    STOE X-SHAPE revision 1.09. Crystal Optimisation for Numerical Absorption Corrections, Darmstadt (Germany): STOE & Cie, 1997.Google Scholar
  24. 24.
    Sheldrick, G.M., Acta Crystallogr., Sect. A: Found. Crystallogr., 1990, vol. 46, no. 6, p. 467.Google Scholar
  25. 25.
    Sheldrick, G.M., SHELXL97. Computer Program for the Refinement of Crystal Structures. Release 97–2 ed., Göttingen, Germany: Univ. of Göttingen, 1997.Google Scholar
  26. 26.
    Flack, H.D., Acta Crystallogr., Sect. A: Found. Crystallogr., 1983, vol. 39, no. 6, p. 876.Google Scholar
  27. 27.
    Hexem, J.G., Frey, M.H., and Opella, S.J., J. Chem. Phys., 1982, vol. 77, no. 7, p. 3847.Google Scholar
  28. 28.
    Harris, R.K., Jonsen, P., and Packer, K.J., Magn. Reson. Chem., 1985, vol. 23, p. 565.Google Scholar
  29. 29.
    Hauptmann, S., Graefe, J., and Remane, H., Lehrbuch der organischen Chemie, Leipzig: VEB Deutscher Verlag für Grundstoffindustrie, 1976.Google Scholar
  30. 30.
    Bocian, D.F., Pickett, H.M., Rounds, T.C., and Strauss, H.L., J. Am. Chem. Soc., 1975, vol. 97, no. 4, p. 687.Google Scholar
  31. 31.
    Boessenkool, I.K. and Boeyens, J.C.A., J. Cryst. Mol. Struct., 1980, vol. 10, nos. 1–2, p. 11.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2003

Authors and Affiliations

  • A. V. Ivanov
    • 1
  • S. A. Zinkin
    • 1
  • W. Forzling
    • 2
  • O. N. Antzutkin
    • 2
  • M. Kritikos
    • 3
  1. 1.Amur Institute of Integrated Research, Far East DivisionRussian Academy of SciencesBlagoveshchenskRussia
  2. 2.Luleå University of TechnologyLuleåSweden
  3. 3.Stockholm UniversityStockholmSweden

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