The solvent effect on the Diels–Alder reaction in ionic liquids: multiparameter linear solvation energy relationships and theoretical analysis

作者: Cinzia Chiappe , Marco Malvaldi , Christian Silvio Pomelli

DOI: 10.1039/C0GC00074D

关键词: SolventComputational chemistryDiels–Alder reactionSolvationIonic bondingSolvent effectsChemistryIonic liquidReaction rateOrganic chemistryReaction mechanism

摘要: This review illustrates how ionic liquid properties can affect Diels–Alder reactions. The mechanisms by which solvents enhance the rate and selectivity of reaction are discussed on basis correlation studies using empirical parameters theoretical calculations.

参考文章(65)
Darryl C. Rideout, Ronald Breslow, Hydrophobic acceleration of Diels-Alder reactions Journal of the American Chemical Society. ,vol. 102, pp. 7816- 7817 ,(1980) , 10.1021/JA00546A048
Samantha Bruzzone, Marco Malvaldi, Cinzia Chiappe, Solvation thermodynamics of alkali and halide ions in ionic liquids through integral equations. Journal of Chemical Physics. ,vol. 129, pp. 074509- 074509 ,(2008) , 10.1063/1.2970931
Y. Marcus, The effectiveness of solvents as hydrogen bond donors Journal of Solution Chemistry. ,vol. 20, pp. 929- 944 ,(1991) , 10.1007/BF00667223
Ana Vidiš, Ernst Küsters, Gottfried Sedelmeier, Paul J. Dyson, Effect of Lewis acids on the Diels-Alder reaction in ionic liquids with different activation modes. Journal of Physical Organic Chemistry. ,vol. 21, pp. 264- 270 ,(2008) , 10.1002/POC.1293
Thibaud P. Caulier, Jacques Reisse, On Sonochemical Effects on the Diels-Alder Reaction Journal of Organic Chemistry. ,vol. 61, pp. 2547- 2548 ,(1996) , 10.1021/JO9520203
Cinzia Chiappe, Marco Malvaldi, Christian Silvio Pomelli, Ab Initio Study of the Diels-Alder Reaction of Cyclopentadiene with Acrolein in a Ionic Liquid by KS-DFT/3D-RISM-KH Theory. Journal of Chemical Theory and Computation. ,vol. 6, pp. 179- 183 ,(2010) , 10.1021/CT900331E
C. Cativiela, J. I. Garcia, J. A. Mayoral, A. J. Royo, L. Salvatella, X. Assfeld, M. F. Ruiz-Lopez, Experimental and theoretical study of the influence of the solvent on asymmetric diels—alder reactions Journal of Physical Organic Chemistry. ,vol. 5, pp. 230- 238 ,(1992) , 10.1002/POC.610050503
C. Cativiela, J. I. Garcia, J. A. Mayoral, A. Avenoza, J. M. Peregrina, M. A. Roy, Development of a model to explain the influence of the solvent on the rate and selectivity of diels–alder reactions Journal of Physical Organic Chemistry. ,vol. 4, pp. 48- 52 ,(1991) , 10.1002/POC.610040108
Kathleen E. Myers, Krishna Kumar, Fluorophobic Acceleration of Diels−Alder Reactions Journal of the American Chemical Society. ,vol. 122, pp. 12025- 12026 ,(2000) , 10.1021/JA0019777