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

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

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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 σR oconstant 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.

Original languageEnglish
Pages (from-to)300-303
Number of pages4
JournalChemistry of Heterocyclic Compounds
Issue number3
Publication statusPublished - Mar 1983


ASJC Scopus subject areas

  • Organic Chemistry

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