The effect of solvent on a Lewis acid catalyzed Diels-Alder reaction, using computed and experimental kinetic isotope effects

Orlando Acevedo, Jeffrey D. Evanseck

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

(Matrix presented) A new transition structure for the Diels-Alder reaction between isoprene and acrolein catalyzed by Et2AlCl is found to reconcile reported discrepancies between computed and observed secondary kinetic isotope effects (KIEs). Including the effect of solvent realigns the computed results with experiment demonstrating the importance of nonbond interactions at transition structures. Comparison of experimental and newly predicted KIE data reaffirms the ability of theory and experiment to probe the mechanism and transition structure geometry of organic reactions.

Original languageEnglish (US)
Pages (from-to)649-652
Number of pages4
JournalOrganic letters
Volume5
Issue number5
DOIs
StatePublished - Mar 6 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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