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 the MPW1B95 density functional. A computational model based on the Hard Soft Acid Base (HSAB) principle was evaluated for its ability to qualitatively and quantitatively predict the regioselectivity, while kinetics and thermodynamics of the reaction were studied through the analysis of the reaction paths leading to the possible regioisomers

Addition of sulfenic acids to monosubstituted acetylenes : a theoretical and experimental study / M.C. Aversa, A. Barattucci, P. Bonaccorsi, A. Contini. - In: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY. - ISSN 0894-3230. - 22:11(2009), pp. 1048-1057. [10.1002/poc.1557]

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

A. Contini
2009

Abstract

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 the MPW1B95 density functional. A computational model based on the Hard Soft Acid Base (HSAB) principle was evaluated for its ability to qualitatively and quantitatively predict the regioselectivity, while kinetics and thermodynamics of the reaction were studied through the analysis of the reaction paths leading to the possible regioisomers
DFT; Hsab principle; Regioselectivity; Sulfenic acids; Syn-addition
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/69033
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