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

被引：20

作者：

Aversa, Maria Chiara ^{[2
]}

Barattucci, Anna ^{[2
]}

Bonaccorsi, Paola ^{[2
]}

Contini, Alessandro ^{[1
]}

机构：

[1] Univ Milan, Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy

[2] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2009年 / 22卷 / 11期

关键词：

DFT; HSAB principle; regioselectivity; sulfenic acids; syn-Addition; DIELS-ALDER REACTIONS; GAS-PHASE; QUANTITATIVE PREDICTION; HYDROGEN ABSTRACTION; ELIMINATION-REACTION; DENSITY FUNCTIONALS; CHEMICAL-REACTIVITY; CARBOHYDRATE FIELD; CARBONYL-COMPOUNDS; METHYL PROPIOLATE;

D O I：

10.1002/poc.1557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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 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 (C) 2009 John Wiley & Sons, Ltd.

引用

页码：1048 / 1057

页数：10

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