Solvent effects and mechanism for a nucleophilic aromatic substitution from QM/MM simulations

被引：87

作者：

Acevedo, O ^{[1
]}

Jorgensen, WL ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 17期

关键词：

D O I：

10.1021/ol049121k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nucleophilic aromatic substitution (SNAr) reaction between azide ion and 4-fluoronitrobenzene has been investigated using QM/MM and DFT/PCM calculations in protic and dipolar aprotic solvents. The effects of solvation on the transition structures, the intermediate Meisenheimer complex, and the rate of reaction are elucidated. The large rate increases in proceeding from protic to dipolar aprotic solvents are only reproduced by the QM/MM methodology.

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页码：2881 / 2884

页数：4

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