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Effect of N-alkyl and N-aralkyl substituents on nucleophilic substitution in the benzimidazole series

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown in the case of the Chichibabin reaction and exchange of chlorine in 2-chlorobenzimidazoles by a piperidine residue that N-alkyl and N-aralkyl groups are arranged in the following order with respect to their effect on the rate of the process (in the order of decreasing rates): CH3>C6H5CH2, C2H5>iso-C3H7, (C6H5)2CH>n-C9H19>tert-C4H9. The overall decrease in the rate on passing to compounds with branched N-substituents is low. It follows from this that steric hindrance to nucleophilic substitution in the 2 position is only of small significance.

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Authors and Affiliations

  1. Rostov State University, 344006, Rostov-on-Don

    M. M. Medvedeva, V. N. Doron'kin, A. F. Pozharskii & V. N. Novikov

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  1. M. M. Medvedeva
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  2. V. N. Doron'kin
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  3. A. F. Pozharskii
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  4. V. N. Novikov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1120–1125, August, 1977.

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Medvedeva, M.M., Doron'kin, V.N., Pozharskii, A.F. et al. Effect of N-alkyl and N-aralkyl substituents on nucleophilic substitution in the benzimidazole series. Chem Heterocycl Compd 13, 903–909 (1977). https://doi.org/10.1007/BF00488920

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  • DOI: https://doi.org/10.1007/BF00488920

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