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

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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.

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Authors and Affiliations

  1. A. E. Favorskii Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk

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

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  1. A. V. Vashchenko
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  2. A. M. Vasil’tsov
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  3. E. Yu. Shmidt
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  4. A. I. Mikhaleva
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  5. B. A. Trofimov
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Original Russian Text Copyright © 2006 by A. V. Vashchenko, A. M. Vasil’tsov, E. Yu. Shmidt, A. I. Mikhaleva, and B. A. Trofimov

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Translated from Zhurnal Strukturnoi Khimii, Vol. 47, No. 4, pp. 636–641, May–June, 2006.

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Vashchenko, A.V., Vasil’tsov, A.M., Shmidt, E.Y. et al. The structure of dihydropyrroloindoles: A quantum-chemical estimation of conjugation in cyclohexadiene systems. J Struct Chem 47, 616–621 (2006). https://doi.org/10.1007/s10947-006-0347-z

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  • DOI: https://doi.org/10.1007/s10947-006-0347-z

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