The acidity of weak carbon acids. Part 5. The kinetic acidities of substituted benzyl cyanides using substituted benzylamines as bases

Abstract

The rate coefficients for the base-catalysed detritiationof a series of meta-substituted benzyl cyanides in DMSO have been measured at 25.0 °C. The bases are a series of meta/para-substituted benzylamines. Brønsted coefficients, α and β, have been calculated from both the known pK_a values of the substrates and measured pK_a values of the conjugate acids of the bases in DMSO. The mean α and β values of ca. 0.72 and 0.64 are close. There is no selectivity–reactivity relationship apparent. The results are related to Marcus and related treatments.