Journal of Structural Chemistry

, Volume 47, Issue 4, pp 616–621 | Cite as

The structure of dihydropyrroloindoles: A quantum-chemical estimation of conjugation in cyclohexadiene systems

  • A. V. Vashchenko
  • A. M. Vasil’tsov
  • E. Yu. Shmidt
  • A. I. Mikhaleva
  • B. A. Trofimov


A non-empirical quantum chemical calculation of isomeric 3,6-divinyl-3,4,5,6-tetrahydropyrrolo[3,2-e] indole 1 and 1,5-divinyl-1,4,5,8-tetrahydro[3,2-f]indole 2 structures carried out by DFT (B3LYP) method with 6-311++G(d, p) and 6-311++G(3df, p) basis sets showed the energy preference of 2 over 1 (1.33 kcal/mol and 1.47 kcal/mol, respectively). The structure of the molecule of 2 is planar while the molecule of 1 is non-planar due to the presence of sp 3-hybridized carbon atoms.


6-tetrahydropyrrolo-e indole cyclohexadiene systems ab initio calculation π-conjugated compound hybridization 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    F. Lucchesini, Tetrahedron, 48, 9951–9966 (1992).CrossRefGoogle Scholar
  2. 2.
    J. Roncali, Chem. Rev., 92, 711–732 (1992).CrossRefGoogle Scholar
  3. 3.
    A. R. Katritzky, J. Li, and M. F. Gordeev, Synthesis, 93–96 (1994).Google Scholar
  4. 4.
    T. E. O. Screen, K. B. Lawton, G. S. Wilson, et al., J. Mater. Chem., 11, 312–320 (2001).CrossRefGoogle Scholar
  5. 5.
    A. O. Patil, A. J. Heeger, and F. Wudl, Chem. Rev., 88, 183–200 (1988).CrossRefGoogle Scholar
  6. 6.
    J. Eldo, E. Arunkumar, and A. Ajayaghosh, Tetrahedron Lett., 41, 6241–6244 (2000).CrossRefGoogle Scholar
  7. 7.
    M. Omastova, M. Trchova, J. Kovarova, and J. Stejskal, Synth. Met., 138, 447–455 (2003).CrossRefGoogle Scholar
  8. 8.
    D. Aldakov and P. Jr. Anzenbacher, Chem. Commun., 1394/1395 (2003).Google Scholar
  9. 9.
    J. Sołoducho, J. Doskocz, J. Cabaj, and S. Roszak, Tetrahedron., 59, 4761–4766 (2003).CrossRefGoogle Scholar
  10. 10.
    H. Z. Chen, Y. D. Jin, R. S. Xu, et al., Synth. Met., 139, 529–534 (2003).CrossRefGoogle Scholar
  11. 11.
    J. J. Klappa, S. A. Geers, S. J. Smidtke, et al., Dalton Trans., 883–891 (2004).Google Scholar
  12. 12.
    B. A. Trofimov, A. B. Zaitsev, E. Yu. Schmidt, et al., Tetrahedron Lett., 45, 3789–3791 (2004).CrossRefGoogle Scholar
  13. 13.
    B. A. Trofimov and A. I. Mikhaleva, N-Vynilpyrroles, Nauka, Novosibirsk (1984).Google Scholar
  14. 14.
    B. A. Trofimov, in: The Chemistry of Heterocyclic Compounds, Part 2, Vol. 48; Pyrroles, R. A. Jones (ed.) Wiley, New York (1992), pp. 131–298.Google Scholar
  15. 15.
    Two-Step Synthesis of Pyrroles from Ketones and Acetylenes Through the Trofimov reaction, A. I. Mikhaleva and E. Yu. Schmidt, Selected Methods for Synthesis and Modification of Heterocycles, V. G. Kartsev (ed.), 1, 334–352, IBS Press, Moscow (2002).Google Scholar
  16. 16.
    A. B. Zaitsev, A. M. Vasil’tsov, E. Yu. Shmidt, et al., Zh. Org. Khim., 39, No. 10, 1479–1483 (2003).Google Scholar
  17. 17.
    H. Z. Chen, Y. D. Jin, R. S. Xu, et al., Synth. Met., 139, 529–534 (2003).CrossRefGoogle Scholar
  18. 18.
    M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 03, Revision B. 03, Gaussian, Pittsburgh PA (2003).Google Scholar
  19. 19.
    F. H. Herbstein, M. Kapon, and G. M. Reisner, Acta Crystallogr., Sect. B: Struct. Sci., 42, 181 (1986); J. P. Reboul, Y. Oddon, C. Caranoni, et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 43, 537 (1987).CrossRefGoogle Scholar
  20. 20.
    K. Moris and J. Laane, J. Mol. Struct., 413/414, 1313–1320 (1997); M. Takanashi, R. Ogino, and Y. Udagawa, Chem. Phys. Lett., 288, 714–718 (1998).CrossRefGoogle Scholar
  21. 21.
    A. Dreiding, Angew. Chem., 76, 501/502 (1964).Google Scholar
  22. 22.
    V. A. Pal’m, An Introduction to Theoretical Organic Chemistry [in Russian], Vysshaya Shkola, Moscow (1974).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • A. V. Vashchenko
    • 1
  • A. M. Vasil’tsov
    • 1
  • E. Yu. Shmidt
    • 1
  • A. I. Mikhaleva
    • 1
  • B. A. Trofimov
    • 1
  1. 1.A. E. Favorskii Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutsk

Personalised recommendations