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Kinetics study of a Diels-Alder reaction in mixtures of an ionic liquid with molecular solvents

Harifi Mood, A. R ; Sharif University of Technology | 2008

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  1. Type of Document: Article
  2. DOI: 10.1002/poc.1377
  3. Publisher: 2008
  4. Abstract:
  5. The second-order rate constants for cycloaddition reaction of cyclopentadiene with naphthoquinone were determined spectrophotometrically in various compositions of 1-(1-butyl)-3-methylimidazolium terafluoroborate ([bmim]BF4) with water and methanol at 25°C. Rate constants of the reaction in pure solvents are in the order of water > [bmim]BF 4 > methanol. Rate constants of the reaction decrease sharply with mole fraction of the ionic liquid in aqueous solutions and increase slightly to a maximum in alcoholic mixtures. Multi-parameter correlation of logk 2 versus solute-solvent interaction parameters demonstrated that solvophobicity parameter (Sp), hydrogen-bond donor acidity (α) and hydrogen-bond acceptor basicity (β) of media are the main factors influencing the reaction rate constant. The proposed three-parameter model shows that the reaction rate constant increases with Sp, α and β parameters. Copyright © 2008 John Wiley & Sons, Ltd
  6. Keywords:
  7. Chemical reactions ; Cycloaddition ; Ionic liquids ; Ionization of liquids ; Ketones ; Olefins ; Reaction kinetics ; Cycloaddition reactions ; Cyclopentadiene ; Diels-Alder ; Diels-Alder reaction ; Ionic liquid ; Kinetics study ; Molecular solvents ; Naphthoquinone ; Second-order rate constants ; Solvent effect ; Rate constants
  8. Source: Journal of Physical Organic Chemistry ; Volume 21, Issue 9 , 2008 , Pages 783-788 ; 08943230 (ISSN)
  9. URL: https://www.onlinelibrary.wiley.com/doi/10.1002/poc.1377