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Acidic properties of N-hetarylacetic acids and inductive constants of N-hetaryl substituents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The inductive constants of the corresponding heterocyclic fragments were calculated on the basis of data on the pKa values obtained by potentiometric titration of derivatives of indole, carbazole, 3-methylcarbazole, tetrahydrocarbazole, 6-methyltetrahydrocarbazole, and phenothiazine. The σ oR constant of the 9-carbazolyl group was also calculated. The enthalpy and entropy of acidic dissociation were calculated from data on the effect of the temperature on the pKa of 9-carbazolylacetic acid. It is shown that the entropy contribution to the free energy of dissociation of 9-carbazolylacetic acid predominates.

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Authors and Affiliations

  1. S. M. Kirov Tomsk Polytechnic Institute, 634004, Tomsk

    T. A. Filippova, M. M. Sukhoroslova, V. P. Lopatinskii & V. D. Filimonov

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  1. T. A. Filippova
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  2. M. M. Sukhoroslova
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  3. V. P. Lopatinskii
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  4. V. D. Filimonov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 369–372, March, 1983.

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Filippova, T.A., Sukhoroslova, M.M., Lopatinskii, V.P. et al. Acidic properties of N-hetarylacetic acids and inductive constants of N-hetaryl substituents. Chem Heterocycl Compd 19, 300–303 (1983). https://doi.org/10.1007/BF00513265

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  • DOI: https://doi.org/10.1007/BF00513265

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