Abstract
Measurement in acetonitrile-methanol of the basicity of selenenamides shows that they are approximately 3 pK units more basic than the corresponding sulfenamides. Since other explanations do not seem tenable, this apparently results from the fact that selenium is less electronegative than sulfur, although it is somewhat surprising that the small difference in the electronegativity of the two elements should lead to such a large difference in basicity. In the same solvent the kinetics of the acid-catalyzed methanolyses (eq 2) of o-nitro- and 2,4,6-tri-tert-butylbenzeneselenenamides are similar (large dependence of rate on [MeOH], unusual dependence of rate on [H + ]) to those for the methanolysis of the corresponding o-nitrobenzenesulfenamides
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