Addition of sulfenic acids to monosubstituted acetylenes: a theoretical and experimental study

摘要

The reaction of benzenesulfenic acid, generated in situ by thermal decomposition of 3-(phenylsulfinyl)propanenitrile,with monosubstituted acetylenes was experimentally and theoretically investigated at the DFT level using theMPW1B95 density functional. A computational model based on the Hard Soft Acid Base (HSAB) principle wasevaluated for its ability to qualitatively and quantitatively predict the regioselectivity, while kinetics and thermo-dynamics of the reaction were studied through the analysis of the reaction paths leading to the possible regioisomers.