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Addition of sulfenic acids to monosubstituted acetylenes: a theoretical and experimental study
Author(s) -
Aversa Maria Chiara,
Barattucci Anna,
Bonaccorsi Paola,
Contini Alessandro
Publication year - 2009
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1557
Subject(s) - hsab theory , regioselectivity , chemistry , sulfenic acid , structural isomer , computational chemistry , thermal decomposition , density functional theory , decomposition , kinetics , organic chemistry , catalysis , cysteine , enzyme , physics , quantum mechanics
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. Copyright © 2009 John Wiley & Sons, Ltd.