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

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Abstract
Hydrogen-bond complexation constants determined by Taylor and co-workers using 1,1,1-trichloroethane (TCE) solvent have been analysed through the α2 Hβ2 H relationship; α2 H and β2 H 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 α2 Hβ2 H relationship in tetrachloromethane, but the intercept is the same. Eqn. (i) has been used to obtain 25 new α2 H values for acids; these include acetanilides, sulfonamides, triazoles and tetrazoles. The latter two types of compound have very large α2 H values; that for 5-phenyl-1,2,3,4-tetrazole (0.88) being near the value for dichloroacetic acid (0.90). Values of β2 H for 31 hydrogen-bond bases have also been calculated using eqn. (i). These include bases with heterocyclic moieties to which β2 H values had not previously been assigned, e.g. oxazole, isoxazole, triazoles and a tetrazole.

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