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 Citations (Scopus)

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 publicationACS Symposium Series
Pages174-190
Number of pages17
Volume856
StatePublished - 2003
Externally publishedYes

Publication series

NameACS Symposium Series
Volume856
ISSN (Print)00976156

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Cyclopentanes
Aluminum chloride
Ionic Liquids
Model structures
Chlorides
Cations
Lewis Acids
Cycloaddition
Anions
Activation energy
methyl acrylate
1-ethyl-3-methylimidazolium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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. / Acevedo, Orlando; Evanseck, Jeffrey D.

ACS Symposium Series. Vol. 856 2003. p. 174-190 (ACS Symposium Series; Vol. 856).

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

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