Chemistry of Heterocyclic Compounds

, Volume 13, Issue 7, pp 739–742 | Cite as

Relative basicities of n-vinylpyrroles

  • B. A. Trofimov
  • N. I. Golovanova
  • A. I. Mikhaleva
  • S. E. Korostova
  • A. N. Vasil'ev
  • L. N. Balabanova
Article
  • 26 Downloads

Abstract

The relative basicities of a series of N-vinylpyrroles and some of their analogs with saturated substituents attached to the nitrogen atom were investigated (the ΔvOH shifts in the IR spectrum of phenol were measured). The vOH values were measured in the interval 100–150 cm−1. Alkyl substituents in the 2 and 3 positions raise the basicity of the pyrrole ring, while a phenyl substituent in the 2 position lowers it. N-Vinyl-pyrroles are ∼25% less basic than their limiting analogs-N-ethyl- and N-(2′-alkylthioethyl)pyrroles. The inductive effect of the substituent makes the major contribution to the basicities of the investigated pyrroles. The ΔvOH values for N-vinyl-2,3-diphenylpyrrole are not in conformity with the general tendencies and constitute evidence for the appreciable contribution of continuous conjugation through the double bond, the pyrrole ring, and the benzene ring in the 3 position.

Keywords

Nitrogen Phenol Benzene Phenyl Double Bond 

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Literature cited

  1. 1.
    A. R. Katritzky, Physical Methods in the Chemistry of Heterocyclic Compounds, Academic Press (1963).Google Scholar
  2. 2.
    A. Gossauer, Die Chemie der Pyrrole, Berlin-Heidelberg-New York (1974), p. 417.Google Scholar
  3. 3.
    B. A. Trofimov, N. I. Shergina, S. E. Korostova, é. I. Kositsyna, O. N. Vylegzhanin, N. A. Nedolya, and M. G. Voronkov, in: Reakts. Sposobnost' Org. Soedin., 8, No. 4, 1047 (1971).Google Scholar
  4. 4.
    B. A. Trofimov, N. I. Shergina, é. I. Kositsyna, E. P. Vyalykh, S. V. Amosova, N. K. Gussarova, and M. G. Voronkov, Reakts. Sposobnost' Org. Soedin., 10, No. 3, 766 (1973).Google Scholar
  5. 5.
    B. A. Trofimov, N. I. Golovanova, A. I. Mikhaleva, S. E. Korostova, and A. S. Atavin, Khim. Geterotsikl. Soedin., No. 9, 1225 (1975).Google Scholar
  6. 6.
    B. A. Trofimov, N. I. Golovanova, A. I. Mikhaleva, S. E. Korostova, A. N. Vasil'ev, and L. N. Balabanova, Khim. Geterotsikl. Soedin., No. 7, 910 (1977).Google Scholar
  7. 7.
    V. K. Potapov, Usp. Khim., 39, No. 11, 2078 (1970).Google Scholar
  8. 8.
    B. A. Trofimov, A. S. Atavin, A. I. Mikhaleva, G, A. Kalabin, and E. G. Chebotareva, Zh. Org. Khim., No. 10, 2205 (1973).Google Scholar
  9. 9.
    B. A. Trofimov, S. E. Korostova, and L. N. Balabanova, Khim. Geterotsikl. Soedin., No. 10, 1425 (1975).Google Scholar
  10. 10.
    B. A. Trofimov, A. S. Atavin, A. I. Mikhaleva, E. G. Chebotareva, and G. A. Kalabin, USSR Author's Certificate No. 463,666 (1974); Byul. Izobr., No. 10, 57 (1975).Google Scholar
  11. 11.
    B. A. Trofimov, S. E. Korostova, A. I. Mikhaleva, L. N. Balabanova, and A. N. Vasil'ev, Khim. Geterotsikl. Soedin., No. 2, 215 (1977).Google Scholar
  12. 12.
    A. I. Mikhaleva, S. E. Korostova, A. N. Vasil'ev, L. N. Balabanova, N. P. Sokol'nikova, and B. A. Trofimov, Khim. Geterotsikl. Soedin. (in press, 1977).Google Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • B. A. Trofimov
    • 1
  • N. I. Golovanova
    • 1
  • A. I. Mikhaleva
    • 1
  • S. E. Korostova
    • 1
  • A. N. Vasil'ev
    • 1
  • L. N. Balabanova
    • 1
  1. 1.Irkutsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRIrkutsk

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