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Acid–base and Hydrogen-bonding Equilibria in Aliphatic Amine and Carboxylic Acid Systems in Non-aqueous Solutions by J. Zielińska; M. Makowski; K. Maj; A. Liwo; L. Chmurzyński is a Chemistry article available to read on EtoBox.

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Acid-base and hydrogen-bonding equilibria in acetic acid -acetate, n-butylammonium cation -n-butylamine and acetic acid (acetate) -n-butylamine (n-butylammonium cation) systems were studied in five polar non-aqueous solvents with varying prototropic and dielectric properties: acetonitrile, acetone, dimethyl sulfoxide, methanol, and propylene carbonate using the potentiometric-titration technique. These systems were designed to model the acid-base and hydrogen-bonding phenomena that involve acid and basic amino-acid side chains in proteins. The obtained order of pK a values of acetic acid and n-butylamine is consistent with the variation of prototropic, basic, dielectric, and hydrogen-bonding properties of the solvents used. The homoconjugation and heteroconjugation constant values decrease with increasing basicity of the solvents; they turn out to be indeterminable in dimethyl sulfoxide (the most basic solvent) for cationic homoconjugation and in methanol (the second most basic solvent) for anionic homoconjugation and heteroconjugation.

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Author

J. Zielińska; M. Makowski; K. Maj; A. Liwo; L. Chmurzyński

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0003-2670)

Published

1999

Language

EN

Field

Chemistry (Physical Sciences)