A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach

被引：0

作者：

Riccardo Bini

Cinzia Chiappe

Veronica L. Mestre

Christian S. Pomelli

Thomas Welton

机构：

[1] Università di Pisa,Dipartimento di Chimica Bioorganica e Biofarmacia

[2] Imperial College London,Dipartimento di Chimica e Chimica Industriale

[3] Università di Pisa,undefined

来源：

Theoretical Chemistry Accounts | 2009年 / 123卷

关键词：

Diels-Alder reaction; Ionic liquids; Ab initio calculations;

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摘要：

The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) in different room temperature ionic liquids containing imidazolium-based cations ([HBIM]+, [BMIM]+ and [BM2IM]+) has been studied at the DFT level using a supermolecular approach. An analysis of the theoretical results shows that the ionic liquid cation coordination affects the equilibrium geometries and electronic structures of the reacting species throughout the reaction pathway leading to changes in reactivity and selectivity. They also indicate that the strong asynchronicity of the Diels-Alder reactions in ionic liquids is due to the polarisation effect of the cation.

引用

页码：347 / 352

页数：5