A rationalization of the solvent effect on the Diels-Alder reaction in ionic liquids using multiparameter linear solvation energy relationships.
The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) having different hydrogen bond acceptor abilities has been carried out in several ionic liquids and molecular solvents in order to obtain information about the factors affecting reactivity and selectivity. The solvent effects on these reactions are examined using multiparameter linear solvation energy relationships. The collected data provide evidence that the solvent effects are a function of both the solvent and the solute. For a solvent effect to be seen, the solute must have a complimentary character; selectivities and rates are determined by the solvent hydrogen bond donation ability (alpha) in the reactions of acrolein and methyl acrylate, but not of acrylonitrile.
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Riccardo
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Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno Pisano 33, 56100, Pisa, Italy.
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Cinzia
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Mestre
Veronica Llopsis
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Pomelli
Christian Silvio
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Welton
Thomas
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D002244:Carbon / Q000737:chemistry*; D006860:Hydrogen Bonding; D052578:Ionic Liquids / Q000737:chemistry*; D007700:Kinetics; D016014:Linear Models; D012997:Solvents / Q000737:chemistry*; D013379:Substrate Specificity
D052578:Ionic Liquids; D012997:Solvents; D002244:Carbon