Advertisement

Basicity of 2-phenyl-5-R-1,3,4-oxadiazoles

  • R. E. Trifonov
  • V. A. Ostrovskii
Article

Abstract

We have studied the basicity of 2-phenyl-5-R-1,3,4-oxadiazoles (R = H, Me, CH2Ph, t-Bu, CH2Cl, CCl3, CF3) in aqueous sulfuric acid solutions. These compounds are weak organic bases (pKBH + is −1.8 to −5.2). The values of pKBH + determined on the H0 and X acidity function scales agree well with each other. The substituent at the 5 position has a substantial effect on the basicity of the 1,3,4-oxadiazole ring.

Keywords

1,3,4-oxadiazoles weak bases basicity UV spectroscopy acidity function electronic substituent constants 

References

  1. 1.
    J. Hill, “1,3,4-Oxadiazoles,” in: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, and R. C. Storr (editors), Comprehensive Heterocyclic Chemistry II, Pergamon, Oxford (1996), Vol. 4, p. 267.Google Scholar
  2. 2.
    G. V. Maier, Photophysical Processes and Lasing Ability of Aromatic Molecules [in Russian], Izdat. Tomskogo Univ., Tomsk (1992).Google Scholar
  3. 3.
    R. E. Trifonov, S. E. Ivanova, V. A. Ostrovskii, and G. I. Koldobskii, Zh. Org. Khim., 30, 1556 (1994).Google Scholar
  4. 4.
    R. E. Trifonov, N. I. Rtishchev, and V. A. Ostrovskii, Spectrochim. Acta, Pt. A, 52, 1875 (1996).CrossRefGoogle Scholar
  5. 5.
    R. Houriet, E. Roll, G. Bouchoux, and Y. Hoppilliard, Helv. Chim. Acta, 68, 2037 (1985).CrossRefGoogle Scholar
  6. 6.
    R. E. Trifonov and V. A. Ostrovskii, Zh. Org. Khim., 37, 441 (2001).Google Scholar
  7. 7.
    R. E. Trifonov, A. P. Volovodenko, S. N. Vergizov, N. I. Shirinbekov, V. A. Gindin, A. O. Koren, and V. A. Ostrovskii, Helv. Chim. Acta, 88, 1790 (2005).CrossRefGoogle Scholar
  8. 8.
    V. A. Ostrovskii and G. I. Koldobskii, Weak Organic Bases [in Russian], Izdat. GLU, Leningrad (1990), p. 145.Google Scholar
  9. 9.
    R. E. Trifonov, Dissertation in competition for the academic degree of Candidate of Chemical Sciences, St. Petersburg (1998).Google Scholar
  10. 10.
    J. Elguero, A. Fruchier, N. Jagerovich, and A. Werner, Org. Prep. Proc. Int., 27, 33 (1995).CrossRefGoogle Scholar
  11. 11.
    J. Catalan, J. L. M. Abboud, and J. Elguero, Adv. Heterocycl. Chem., 41, 187 (1987).CrossRefGoogle Scholar
  12. 12.
    G. I. Koldobskii and V. A. Ostrovskii, Usp. Khim., 63, 867 (1994).Google Scholar
  13. 13.
    L. M. Stock and M. R. Wasielewski, Prog. Phys. Org. Chem., 13, 253 (1981).Google Scholar
  14. 14.
    Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], Izdat. Rost. Univ., Rostov-na-Donu (1966).Google Scholar
  15. 15.
    R. A. Cox and K. Yates, Can. J. Chem., 61, 2225 (1983).CrossRefGoogle Scholar
  16. 16.
    C. Hansch and A. Leo, Exploring QSAR. Vol. 2: Hydrophobic, Electronic, and Steric Constants, Wiley, New York (1995).Google Scholar
  17. 17.
    R. Huisgen, J. Sauer, H. J. Sturm, and J. H. Markgraf, Chem. Ber., 93, 2106 (1960).Google Scholar
  18. 18.
    F. Povazanec, J. Kovac, and J. Svoboda, Collect. Czech. Chem. Commun., 45, 1299 (1980).Google Scholar
  19. 19.
    B. S. Jursic and Z. Zdravkovski, Synth. Commun., 24, 1575 (1994).Google Scholar
  20. 20.
    M. P. Hutt, E. Elslager, and L. M. Werbel, J. Heterocycl. Chem., 7, 511 (1970).CrossRefGoogle Scholar
  21. 21.
    I. S. Poddubnyi, L. I. Belen’kii, M. I. Struchkova, and M. M. Krayushkin, Khim. Geterotsikl. Soedin., 729 (1994).Google Scholar
  22. 22.
    G. W. Weaver, Science of Synthesis, 13, 219 (2004).Google Scholar
  23. 23.
    E. P. Nesynov and A. P. Grekov, Usp. Khim., 33, 1184 (1964).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • R. E. Trifonov
    • 1
  • V. A. Ostrovskii
    • 1
  1. 1.St. Petersburg State Technical UniversitySt. PetersburgRussia

Personalised recommendations