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

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 [BM 2 IM] + ) has been studied at the DFT level using a supermolecular approa...

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Bibliographic Details
Published in:Theoretical chemistry accounts 2009-06, Vol.123 (3-4), p.347-352
Main Authors: Bini, Riccardo, Chiappe, Cinzia, Mestre, Veronica L., Pomelli, Christian S., Welton, Thomas
Format: Article
Language:English
Subjects:
Atomic/Molecular Structure and Spectra
Chemistry
Chemistry and Materials Science
Inorganic Chemistry
Organic Chemistry
Physical Chemistry
Regular Article
Theoretical and Computational Chemistry
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Summary: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 [BM 2 IM] + ) 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.
ISSN:1432-881X
1432-2234
DOI:10.1007/s00214-009-0525-0