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Effect of nucleophile on the activation parameters of transesterification of 4-nitrophenyl benzoates

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Abstract

Activation parameters of the reaction of 4-nitrophenyl benzoates with benzenethiol in the presence of potassium carbonate in dimethylformamide were determined. The entropies of activation for the reactions of unsubstituted 4-nitrophenyl benzoate and 4-nitrophenyl benzoates having donor substituents are positive. The relative contributions of the enthalpy and entropy of activation to the Gibbs energy of activation are discussed. Variation of the activation parameters upon replacement of benzenethiol by 4-chlorophenol is analyzed.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    I. A. Os’kina & V. M. Vlasov

Authors
  1. I. A. Os’kina
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  2. V. M. Vlasov
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Correspondence to I. A. Os’kina.

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Original Russian Text © I.A. Os’kina, V.M. Vlasov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 3, pp. 334–338.

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Os’kina, I.A., Vlasov, V.M. Effect of nucleophile on the activation parameters of transesterification of 4-nitrophenyl benzoates. Russ J Org Chem 46, 326–330 (2010). https://doi.org/10.1134/S1070428010030048

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  • DOI: https://doi.org/10.1134/S1070428010030048

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