Abstract
Abstract The extent of protonation of several N-sulphonyl sulphilimines of XC 6 H 4 (Me)SNTs and MePhSNSO 2 C 6 H 4 Y type has been measured in aqueous sulphuric acid by the UV technique. Sulphilimines follow the H o acidity function and thermodynamic pK a 's can be calculated from the equation given for Hammett-bases. The pK a 's range from −1·81 (X = p -OMe) to −3·00 (Y = p -NO 2 ). Structural effects on the basicity of the SNS group are similar to those of the SO group in sulphoxides. The Hammett ϱ values for substituted sulphilimines are ϱ X = +0·89 and ϱ Y = +0·82. The basicities of sulphilimines are discussed and compared to those of nitrogen(sp 2 ) bases and other sulphur compounds.
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