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

Research output: Contribution to journalArticle

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 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
Volume19
Issue number3
DOIs
Publication statusPublished - Mar 1983

ASJC Scopus subject areas

  • Organic Chemistry

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