Russian Journal of General Chemistry

, Volume 75, Issue 10, pp 1517–1523 | Cite as

Kinetics and Mechanism of Monomolecular Heterolysis of Commercial Organohalogen Compounds: XLII. Effect of Aprotic Solvent on the Rate of 3-Methyl-3-chloro-1-butene Dehydrochlorination. Correlation Analysis of Solvation Effects

  • N. E. Ponomarev
  • V. V. Zaliznyi
  • G. F. Dvorko


The kinetics of 3-methyl-3-chloro-1-butene dehydrochlorination in propylene carbonate, γ-butyrolactone, sulfolane, acetone, MeCN, PhNO2, PhCN, PhCOMe, MeCOEt, cyclohexanone, o-dichlorobenzene, PhCl, PhBr, 1,2-dichloroethane, dioxane, and AcOEt were studied; v = k[C5H9Cl], E1 mechanism. The reaction rate is satisfactorily described by the parameters of the polarity, electrophilicity, and cohesion of the solvent; the solvent nucleophilicity and polarizability exert no effect on the reaction rate.


MeCN Cyclohexanone Propylene Carbonate AcOEt Sulfolane 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Ponomarev, N.E., Zaliznyi, V.V., and Dvorko, G.F., Zh. Obshch. Khim., 2005, vol. 75, no.9, p. 1503.Google Scholar
  2. 2.
    Dvorko, G.F., Ponomarev, N.E., and Ponomareva, E.A., Zh. Obshch. Khim., 1999, vol. 69, no.11, p. 1835.Google Scholar
  3. 3.
    Dvorko, G.F., Ponomareva, E.A., and Ponomarev, M.E., J. Phys. Org. Chem., 2004, vol. 17, no.4, p. 825.Google Scholar
  4. 4.
    Dvorko, G.F., Zaliznyi, V.V., and Ponomarev, N.E., Zh. Obshch. Khim., 2002, vol. 72, no.10, p. 1644.Google Scholar
  5. 5.
    Dvorko, G.F., Kulik, N.I., and Ponomarev, N.E., Zh. Obshch. Khim., 1995, vol. 65, no.6, p. 1003.Google Scholar
  6. 6.
    Dvorko, G.F., Koshchii, I.V., and Ponomareva, E.A., Zh. Obshch. Khim., 2003, vol. 73, no.1, p. 110.Google Scholar
  7. 7.
    Dvorko, G.F., Koshchii, I.V., Prokopets, A.M., and Ponomareva, E.A., Zh. Obshch. Khim., 2002, vol. 72, no.11, p. 1902.Google Scholar
  8. 8.
    Dvorko, G.F., Pervishko, T.L., Golovko, N.I., Vasil'kevich, A.I., and Ponomareva, E.A., Zh. Org. Khim., 1993, vol. 29, no.9, p. 1805.Google Scholar
  9. 9.
    Dvorko, G.F. and Cherevach, T.V., Zh. Obshch. Khim., 1988, vol. 58, no.6, p. 1371.Google Scholar
  10. 10.
    Ponomarev, N.E., Yakhimovich, R.I., and Kulik, N.I., Zh. Obshch. Khim., 1988, vol. 58, no.5, p. 1106.Google Scholar
  11. 11.
    Ponomarev, N.E., Stambirskii, M.V., Dvorko, G.F., and Bazil'chuk, A.V., Zh. Org. Khim., 2004, vol. 40, no.4, p. 520.Google Scholar
  12. 12.
    Reichardt, Ch., Solvents and Solvent Effects in Organic Chemistry, Weinheim: VCH, 1988.Google Scholar
  13. 13.
    Pross, A. and Shaik, S.S., Acc. Chem. Res., 1983, vol. 16, no.1, p. 363.CrossRefGoogle Scholar
  14. 14.
    Kim, H.J. and Hynes, J.T., J. Am. Chem. Soc., 1992, vol. 114, no.26, p. 10 508.Google Scholar
  15. 15.
    Dvorko, G.F. and Ponomareva, E.A., Usp. Khim., 1991, vol. 60, no.10, p. 2089.Google Scholar
  16. 16.
    Palm, V.A., Osnovy kolichestvennoi teorii organicheskikh reaktsii (Principles of the Quantitative Theory of Organic Reactions), Leningrad: Khimiya, 1977.Google Scholar
  17. 17.
    Makitra, R.G. and Pirig, Ya.N., Zh. Obshch. Khim., 1986, vol. 56, no.3, p. 657.Google Scholar
  18. 18.
    Abraham, M.H., Taft, R.W., and Kamlet, M.J., J. Org. Chem., 1981, vol. 46, no.15, p. 3053.CrossRefGoogle Scholar
  19. 19.
    Abboud, J.-L.M. and Notario, P., Pure Appl. Chem., 1999, vol. 71, no.4, p. 645.Google Scholar
  20. 20.
    Marcus, Y., Chem. Soc. Rev., 1993, vol. 22, no.6, p. 490.CrossRefGoogle Scholar
  21. 21.
    Kafarov, V.V., Metody kibernetiki v khimii i khimicheskoi tekhnologii (Methods of Cybernetics in Chemistry and Chemical Technology), Moscow: Khimiya, 1971, p. 496.Google Scholar
  22. 22.
    Dvorko, G.F., Koshchii, I.V., Prokopets, A.M., and Ponomareva, E.A., Zh. Obshch. Khim., 2002, vol. 72, no.12, p. 1989.Google Scholar
  23. 23.
    Vasil'kevich, A.I., Ponomareva, E.A., and Dvorko, G.F., Zh. Org. Khim., 1990, vol. 26, no.11, p. 2267.Google Scholar
  24. 24.
    Dvorko, G.F., Zhovtyak, V.N., and Evtushenko, N.Yu., Zh. Obshch. Khim., 1989, vol. 59, no.7, p. 1600.Google Scholar
  25. 25.
    Okamoto, K., Pure Appl. Chem., 1984, vol. 56, no.12, p. 1798.Google Scholar
  26. 26.
    Kinoshita, T., Ueno, T., Tkai, K., Fujiwara, M., and Okamoto, K., Bull. Chem. Soc. Jpn., 1988, vol. 61, no.9, p. 3273.Google Scholar
  27. 27.
    Ponomarev, N.E., Stambirskii, M.V., and Dvorko, G.F., Zh. Obshch. Khim., 2005, vol. 75, no.6, p. 937.Google Scholar
  28. 28.
    Bentley, T.W. and Schleyer, P.v.R., Adv. Phys. Org. Chem., 1977, vol. 14, no.1, p. 1.Google Scholar
  29. 29.
    Bentley, T.W. and Llewellyn, G., Prog. Phys. Org. Chem., 1990, vol. 17, p. 121.Google Scholar
  30. 30.
    Sneen, R.A. and Kay, P.S., J. Am. Chem. Soc., 1972, vol. 94, no.20, p. 6983.Google Scholar
  31. 31.
    Kuhn, R. and Trischman, H., Monatsh. Chem., 1964, vol. 95, no.2, p. 457.CrossRefGoogle Scholar
  32. 32.
    Weissberger, A. and Proskauer, E.S., Organic Solvents. Physical Properties and Methods of Purification, Riddick, J.A. and Toops, E.E., Eds., New York: Interscience, 1955.Google Scholar

Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • N. E. Ponomarev
    • 1
  • V. V. Zaliznyi
    • 1
  • G. F. Dvorko
    • 1
  1. 1.Kiev Polytechnic InstituteNational Technical University of UkraineKievUkraine

Personalised recommendations