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Dipole moments of pyrroles polarized by push-pull combination of substituents

  • B. A. Trofimov
  • V. B. Modonov
  • T. N. Aksamentova
  • A. I. Mikhaleva
  • S. E. Korostova
  • L. N. Sobenina
  • R. N. Nesterenko
  • R. I. Polovnikova
Physical Chemistry
  • 27 Downloads

Conclusions

  1. 1.

    In 2-aryl- and 2-hetaryl-5-trifluoroaeetylpyrroles, the interaction of substituants through the pyrrole ring causes a strong polarization of the molecule.

     
  2. 2.

    The dipole moments of 2-aryl-5-trifluoroaeetylpyrroles are very sensitive to the donor properties of the aryl group and are linearly related to a constants of the para-substituents in the benzene ring (σ=3.35).

     
  3. 3.

    The N-vinyl group markedly intensifies the shift of the electrons in the direction of the acceptor as the result of the polarization of the double bond, compensating the positive charge on the nitrogen atom.

     

Keywords

Nitrogen Benzene Double Bond Dipole Moment Nitrogen Atom 
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.

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Literature cited

  1. 1.
    B. A. Trofimov, V. B. Modonov, T. N. Aksamentov, Zh. Obshch. Khim.,53, 1867 (1983).Google Scholar
  2. 2.
    B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Nauka, Novosibirsk (1984), pp. 169–178.Google Scholar
  3. 3.
    V. B. Modonov, B. A. Trofimov, A. I. Mikhaleva, and R. I. Nesterenko, “Dipole moments and structure of 2-(2-thienyl) pyrroles,” Summaries of Lectures at the XVIth Conference on the Chemistry and Technology of Organic Sulfur Compounds and Sulfur-Containing Oils [in Russian], Riga (1984), pp. 286–287.Google Scholar
  4. 4.
    B. A. Trofimov, M. V. Sigalov, S. I. Tandura, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1122 (1979).Google Scholar
  5. 5.
    B. A. Trofimov, Heteroatomic Derivatives of Acetylene; New Polyfunctional Monomers, Reagents and Intermediate Products [in Russian], Nauka, Moscow (1981), p. 319.Google Scholar
  6. 6.
    B. A. Trofimov and A. I. Mikhaleva, Khim. Geterotsikl. Soedin., 1299 (1980).Google Scholar
  7. 7.
    B. A. Trofimov, A. I. Mikhaleva, S. E. Korostova, et al. Zh. Org. Khim.,15, 2042 (1979).Google Scholar
  8. 8.
    B. A. Trofimov, S. E. Korostova, A. I. Mikhaleva, et al., Zh. Org. Khim.,18, 894 (1982).Google Scholar

Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • B. A. Trofimov
    • 1
  • V. B. Modonov
    • 1
  • T. N. Aksamentova
    • 1
  • A. I. Mikhaleva
    • 1
  • S. E. Korostova
    • 1
  • L. N. Sobenina
    • 1
  • R. N. Nesterenko
    • 1
  • R. I. Polovnikova
    • 1
  1. 1.Siberian BranchIrkutsk Institute of Organic Chemistry, Academy of Sciences of the USSRUSSR

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