Acidities of 1-indolylacetic and carbazolylacetic acids. Inductive constants of indolyl and carbazolyl groups

Abstract

The pK_a values of 1-indolylacetic, 3-(9-ethyl)carbazolylacetic, and a number of 3,6-disubstituted 9-carbazolylacetic acids in aqueous ethanol solutions were determined by potentiometry.The inductive constants of the corresponding heterocyclic fragments were calculated from the values obtained. It is shown that annelation of the benzene ring with the pyrrole ring of indole gives rise to a decrease in the negative inductive effect of the heteroring. A linear relationship between the acidic properties of carbazoles and the corresponding 9-carbazolylacetic acids was established.

Original language	English
Pages (from-to)	1213-1216
Number of pages	4
Journal	Chemistry of Heterocyclic Compounds
Volume	17
Issue number	12
DOIs	https://doi.org/10.1007/BF00506996
Publication status	Published - Dec 1981

ASJC Scopus subject areas

Organic Chemistry

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10.1007/BF00506996

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@article{08abfa6d4f2542d583b981bf2fad9219,

title = "Acidities of 1-indolylacetic and carbazolylacetic acids. Inductive constants of indolyl and carbazolyl groups",

abstract = "The pKa values of 1-indolylacetic, 3-(9-ethyl)carbazolylacetic, and a number of 3,6-disubstituted 9-carbazolylacetic acids in aqueous ethanol solutions were determined by potentiometry.The inductive constants of the corresponding heterocyclic fragments were calculated from the values obtained. It is shown that annelation of the benzene ring with the pyrrole ring of indole gives rise to a decrease in the negative inductive effect of the heteroring. A linear relationship between the acidic properties of carbazoles and the corresponding 9-carbazolylacetic acids was established.",

author = "Filimonov, {V. D.} and Sukhoroslova, {M. M.} and Novikov, {V. T.} and Vidyagina, {T. V.}",

year = "1981",

month = dec,

doi = "10.1007/BF00506996",

language = "English",

volume = "17",

pages = "1213--1216",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "12",

}

TY - JOUR

T1 - Acidities of 1-indolylacetic and carbazolylacetic acids. Inductive constants of indolyl and carbazolyl groups

AU - Filimonov, V. D.

AU - Sukhoroslova, M. M.

AU - Novikov, V. T.

AU - Vidyagina, T. V.

PY - 1981/12

Y1 - 1981/12

N2 - The pKa values of 1-indolylacetic, 3-(9-ethyl)carbazolylacetic, and a number of 3,6-disubstituted 9-carbazolylacetic acids in aqueous ethanol solutions were determined by potentiometry.The inductive constants of the corresponding heterocyclic fragments were calculated from the values obtained. It is shown that annelation of the benzene ring with the pyrrole ring of indole gives rise to a decrease in the negative inductive effect of the heteroring. A linear relationship between the acidic properties of carbazoles and the corresponding 9-carbazolylacetic acids was established.

AB - The pKa values of 1-indolylacetic, 3-(9-ethyl)carbazolylacetic, and a number of 3,6-disubstituted 9-carbazolylacetic acids in aqueous ethanol solutions were determined by potentiometry.The inductive constants of the corresponding heterocyclic fragments were calculated from the values obtained. It is shown that annelation of the benzene ring with the pyrrole ring of indole gives rise to a decrease in the negative inductive effect of the heteroring. A linear relationship between the acidic properties of carbazoles and the corresponding 9-carbazolylacetic acids was established.

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DO - 10.1007/BF00506996

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JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

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