Advertisement

Chemistry of Heterocyclic Compounds

, Volume 27, Issue 6, pp 583–590 | Cite as

Quantum-chemical investigation of the protonated forms of 2-(2-furyl)pyrrole

  • A. B. Trofimov
  • B. A. Trofimov
  • N. M. Vitkovskaya
  • M. V. Sigalov
Article
  • 28 Downloads

Abstract

The electron and conformational structures, as well as the internal rotation, of 2-(2-furyl)pyrrole and its α-protonated forms were studied by the MNDO method with complete optimization of the geometry. In conformity with the experiments (PMR), the two delocalized cations with a cis orientation of the heteroatoms that are formed as a result of protonation of the pyrrole or furan ring have the greatest and virtually equal stabilities (δH=738.7 and 740.6 kJ/mole).

Keywords

Organic Chemistry Pyrrole Furan Internal Rotation Protonated Form 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    M. Bambagiotti, E. Castelluchi, and G. Strana, Spectrochim. Acta, 30, 1413 (1974).Google Scholar
  2. 2.
    L. Bellito, C. Petrongolo, C. A. Veracini, and M. Bambagiotti, J. Chem. Soc., Perkin 2, 314 (1977).Google Scholar
  3. 3.
    V. Galasso, L. Klasinc, A. Sabljic, N. Trinajistic, G. C. Pappalardo, and W. Steglich, J. Chem. Soc., Perkin 2 127 (1981).Google Scholar
  4. 4.
    M. Milun and N. Trinajistic, Spectr. Lett., 6, 329 (1973).Google Scholar
  5. 5.
    W. Flitsen, H. Peeters, W. Semulten, and P. Rademacher, Tetrahedron, 34, 2301 (1978).Google Scholar
  6. 6.
    E. Orti, J. Sanchez-Marin, J. Planelles, and F. Tomas, J. Mol. Structure, THEOCHEM, 124, 307 (1985).Google Scholar
  7. 7.
    E. Orti, J. Sanchez-Marin, and F. Tomas, J. Mol. Structure, THEOCHEM, 124 (1985).Google Scholar
  8. 8.
    E. Orti, J. Sanchez-Marin, M. Merchan, and F. Tomas, J. Phys. Chem., 91, 545 (1987).Google Scholar
  9. 9.
    H. Münshtedt, H. Naarmann, and G. Köhler, Mol. Struct. Liq. Cryst., 118, 129 (1985).Google Scholar
  10. 10.
    M. V. Sigalov, E. O. Shmidt, and B. A. Trofimov, Izv. Akad. Nauk SSSR, Ser. Khim., 2136 (1988).Google Scholar
  11. 11.
    M. V. Sigalov, E. Yu. Shmidt, A. B. Trofimov, and B. A. Trofimov, Khim. Geterotsikl. Soedin., No. 10, 1343 (1989).Google Scholar
  12. 12.
    W. Fabian, Z. Naturforsch., 42a, 641 (1987).Google Scholar
  13. 13.
    M. V. Sigalov, E. Yu. Shmidt, A. I. Mikhaleva, S. E. Korostova, I. M. Lazarev, and B. A. Trofimov, Khim. Geterotsikl. Soedin., No. 8 (1991, in press).Google Scholar
  14. 14.
    L. Radom, W. J. Hehre, and J. A. Pople, J. Amer. Chem. Soc., 94, 2371 (1972).Google Scholar
  15. 15.
    N. Russo, M. Toscano, V. Baroni, and C. Minichino, J. Chim. Phys., 84, 735 (1987).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • A. B. Trofimov
    • 1
  • B. A. Trofimov
    • 1
  • N. M. Vitkovskaya
    • 1
  • M. V. Sigalov
    • 1
  1. 1.Irkutsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRIrkutsk

Personalised recommendations