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Comparison of the electronic and steric structures of 1-vinyl-and 1-(prop-1-en-1-yl)pyrroles according to the 1H and 13C NMR data

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Abstract

According to the 1H and 13C NMR data, 1-isopropenylpyrroles are characterized by larger dihedral angles between the heteroring and exocyclic double bond planes, as compared to isostructural 1-vinylpyrroles, due to steric effect of the α-methyl group in the propenyl fragment. As a result, p-π conjugation with the propenyl group is weaker than with the vinyl group. The propenyl group in 1-isopropenylpyrrole having no other substituents in the heteroring is forced out from the heteroring plane, while the 1-vinylpyrrole molecule is planar. If substituents are present in positions 2 and 5 of the pyrrole ring, the propenyl group on the nitrogen atom becomes orthogonal with respect to the pyrrole ring plane, so that no p-π conjugation is possible. The steric structures of (E)-1-(prop-1-en-1-yl)pyrrole and (Z)-1-(prop-1-en-1-yl)pyrrole are different: the propenyl group in the former is turned relative to the heteroring plane, while the latter molecule is planar.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. V. Afonin, I. A. Ushakov, D. E. Simonenko, O. A. Tarasova, M. A. Maksimova & B. A. Trofimov

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  1. A. V. Afonin
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  2. I. A. Ushakov
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  3. D. E. Simonenko
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  4. O. A. Tarasova
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  5. M. A. Maksimova
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  6. B. A. Trofimov
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Original Russian Text © A.V. Afonin, I.A. Ushakov, D.E. Simonenko, O.A. Tarasova, M.A. Maksimova, B.A. Trofimov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 398–405.

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Afonin, A.V., Ushakov, I.A., Simonenko, D.E. et al. Comparison of the electronic and steric structures of 1-vinyl-and 1-(prop-1-en-1-yl)pyrroles according to the 1H and 13C NMR data. Russ J Org Chem 43, 397–405 (2007). https://doi.org/10.1134/S1070428007030116

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  • DOI: https://doi.org/10.1134/S1070428007030116

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