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

The Kizhner Research Center

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Abstract

The inductive constants of the corresponding heterocyclic fragments were calculated on the basis of data on the pK_a values obtained by potentiometric titration of derivatives of indole, carbazole, 3-methylcarbazole, tetrahydrocarbazole, 6-methyltetrahydrocarbazole, and phenothiazine. The σ_R ^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 pK_a of 9-carbazolylacetic acid. It is shown that the entropy contribution to the free energy of dissociation of 9-carbazolylacetic acid predominates.

Original language	English
Pages (from-to)	300-303
Number of pages	4
Journal	Chemistry of Heterocyclic Compounds
Volume	19
Issue number	3
DOIs	https://doi.org/10.1007/BF00513265
Publication status	Published - Mar 1983

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Organic Chemistry

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Filippova, T. A., Sukhoroslova, M. M., Lopatinskii, V. P., & Filimonov, V. D. (1983). Acidic properties of N-hetarylacetic acids and inductive constants of N-hetaryl substituents. Chemistry of Heterocyclic Compounds, 19(3), 300-303. https://doi.org/10.1007/BF00513265

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AU - Filippova, T. A.

AU - Sukhoroslova, M. M.

AU - Lopatinskii, V. P.

AU - Filimonov, V. D.

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N2 - 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.

AB - 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.

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10.1007/BF00513265