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

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

ASJC Scopus subject areas

Organic Chemistry

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10.1007/BF00513265

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@article{2e8d819a731a4ffc8af0f861f2ebb357,

title = "Acidic properties of N-hetarylacetic acids and inductive constants of N-hetaryl substituents",

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.",

author = "Filippova, {T. A.} and Sukhoroslova, {M. M.} and Lopatinskii, {V. P.} and Filimonov, {V. D.}",

year = "1983",

month = mar,

doi = "10.1007/BF00513265",

language = "English",

volume = "19",

pages = "300--303",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "3",

}

TY - JOUR

T1 - Acidic properties of N-hetarylacetic acids and inductive constants of N-hetaryl substituents

AU - Filippova, T. A.

AU - Sukhoroslova, M. M.

AU - Lopatinskii, V. P.

AU - Filimonov, V. D.

PY - 1983/3

Y1 - 1983/3

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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U2 - 10.1007/BF00513265

DO - 10.1007/BF00513265

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EP - 303

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

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