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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
Article

Abstract

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.

Keywords

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

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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

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