Transition structure models of organic reactions in chloroaluminate ionic liquids cyclopentadiene and methyl acrylate diels-alder reaction in acidic and basic melts of 1-ethyl-3-methylimidazolium chloride with aluminum(III) chloride

Orlando Acevedo, Jeffrey D. Evanseck

Research output: Chapter in Book/Report/Conference proceedingConference contribution

6 Scopus citations

Abstract

The four-stereospecific Diels-Alder transition structures for the cyclopentadiene and methyl acrylate cycloaddition have been computed using the Becke three-parameter density functional tiieory widi the 6-31G(d) basis set within basic and acidic ionic melt approximations. The computational model includes 1-ethyl-3-memylimidazolium cation (EMI+) and chloroaluminates (AlCl4- and Al2Cl 7-) in a stacked configuration which exploits lessons learned from other Lewis acid catalyzed Diels-Alder reactions. Several orientations and possible interactions have been attempted in stationary point determinations. The computed activation energies, structures and vibrations indicate that stacked models may explain experimental data. Large scale density functional computations are necessary to probe larger models including several anion and cation layers, and the inclusion of bulk phase effects.

Original languageEnglish (US)
Title of host publicationIonic Liquids as Green Solvent - Progress and Prospects
EditorsRobin Rogers, Kenneth Seddon
Pages174-190
Number of pages17
StatePublished - Dec 1 2003
Externally publishedYes

Publication series

NameACS Symposium Series
Volume856
ISSN (Print)0097-6156

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Acevedo, O., & Evanseck, J. D. (2003). Transition structure models of organic reactions in chloroaluminate ionic liquids cyclopentadiene and methyl acrylate diels-alder reaction in acidic and basic melts of 1-ethyl-3-methylimidazolium chloride with aluminum(III) chloride. In R. Rogers, & K. Seddon (Eds.), Ionic Liquids as Green Solvent - Progress and Prospects (pp. 174-190). (ACS Symposium Series; Vol. 856).