Acid-Base Equilibria in Benzene. I. A Colligative Property and Infrared Study of the Reactions of Some Carboxylic Acids and Nitrogen Bases

Stanley Bruckenstein; Atsuoshi Saito

doi:10.1021/ja01082a004

Acid-Base Equilibria in Benzene. I. A Colligative Property and Infrared Study of the Reactions of Some Carboxylic Acids and Nitrogen Bases

Stanley Bruckenstein
, Atsuoshi Saito

Chemistry

University of Minnesota Twin Cities

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

The reaction of primary, secondary, and tertiary amines (B) with carboxylic acids (HX) in benzene as solvent was studied at a base concentration of 0.01 M. A dynamic differential vapor pressure technique and infrared spectroscopy were used to establish the stoichiometry of the acid-base reactions. The principal species identified were ion pairs and other uncharged ionic aggregates. Three types of ion pairs are postulated: (1) BH+X-, (2) BH+HX₂ - and (3) BH-X(HX)₂. These ion pairs tend to form oligomers; the stronger the acid or base, the greater the oligomer formation. Reaction of mixtures of two bases with an acid indicates that specific, strong interactions can occur between ion pairs containing different cations.

Original language	English
Pages (from-to)	698-710
Number of pages	13
Journal	Journal of the American Chemical Society
Volume	87
Issue number	4
DOIs	https://doi.org/10.1021/ja01082a004
State	Published - 1965

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title = "Acid-Base Equilibria in Benzene. I. A Colligative Property and Infrared Study of the Reactions of Some Carboxylic Acids and Nitrogen Bases",

abstract = "The reaction of primary, secondary, and tertiary amines (B) with carboxylic acids (HX) in benzene as solvent was studied at a base concentration of 0.01 M. A dynamic differential vapor pressure technique and infrared spectroscopy were used to establish the stoichiometry of the acid-base reactions. The principal species identified were ion pairs and other uncharged ionic aggregates. Three types of ion pairs are postulated: (1) BH+X-, (2) BH+HX2 - and (3) BH-X(HX)2. These ion pairs tend to form oligomers; the stronger the acid or base, the greater the oligomer formation. Reaction of mixtures of two bases with an acid indicates that specific, strong interactions can occur between ion pairs containing different cations.",

author = "Stanley Bruckenstein and Atsuoshi Saito",

year = "1965",

doi = "10.1021/ja01082a004",

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journal = "Journal of the American Chemical Society",

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T1 - Acid-Base Equilibria in Benzene. I. A Colligative Property and Infrared Study of the Reactions of Some Carboxylic Acids and Nitrogen Bases

AU - Bruckenstein, Stanley

AU - Saito, Atsuoshi

PY - 1965

Y1 - 1965

N2 - The reaction of primary, secondary, and tertiary amines (B) with carboxylic acids (HX) in benzene as solvent was studied at a base concentration of 0.01 M. A dynamic differential vapor pressure technique and infrared spectroscopy were used to establish the stoichiometry of the acid-base reactions. The principal species identified were ion pairs and other uncharged ionic aggregates. Three types of ion pairs are postulated: (1) BH+X-, (2) BH+HX2 - and (3) BH-X(HX)2. These ion pairs tend to form oligomers; the stronger the acid or base, the greater the oligomer formation. Reaction of mixtures of two bases with an acid indicates that specific, strong interactions can occur between ion pairs containing different cations.

AB - The reaction of primary, secondary, and tertiary amines (B) with carboxylic acids (HX) in benzene as solvent was studied at a base concentration of 0.01 M. A dynamic differential vapor pressure technique and infrared spectroscopy were used to establish the stoichiometry of the acid-base reactions. The principal species identified were ion pairs and other uncharged ionic aggregates. Three types of ion pairs are postulated: (1) BH+X-, (2) BH+HX2 - and (3) BH-X(HX)2. These ion pairs tend to form oligomers; the stronger the acid or base, the greater the oligomer formation. Reaction of mixtures of two bases with an acid indicates that specific, strong interactions can occur between ion pairs containing different cations.

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JF - Journal of the American Chemical Society

IS - 4

ER -

Acid-Base Equilibria in Benzene. I. A Colligative Property and Infrared Study of the Reactions of Some Carboxylic Acids and Nitrogen Bases

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