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DOI: 10.1039/A702326J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 187-192

Analysis of hydrogen-bond complexation constants in 1,1,1-trichloroethane: the α2Hβ2H relationship

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Michael H. Abraham, Michel Berthelot, Christian Laurence and Peter J. Taylor

Abstract

Hydrogen-bond complexation constants determined by Taylor and co-workers using 1,1,1-trichloroethane (TCE) solvent have been analysed through the α2Hβ2H relationship; α2H and β2H are the solute hydrogen-bond acidity and basicity parameters obtained from complexation constants in tetrachloromethane. Constants for three alcohol/N-methylpyrrolidinone complexations have been determined in TCE, and if these are used instead of the original alcohol/N-methylpyrrolidinone complexation constants, a good relationship is obtained, eqn. (i)

. The slope in eqn. (i) is smaller than that for the α2Hβ2H relationship in tetrachloromethane, but the intercept is the same.

Eqn. (i) has been used to obtain 25 new α2H values for acids; these include acetanilides, sulfonamides, triazoles and tetrazoles. The latter two types of compound have very large α2H values; that for 5-phenyl-1,2,3,4-tetrazole (0.88) being near the value for dichloroacetic acid (0.90). Values of β2H for 31 hydrogen-bond bases have also been calculated using eqn. (i). These include bases with heterocyclic moieties to which β2H values had not previously been assigned, e.g. oxazole, isoxazole, triazoles and a tetrazole.

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