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Combined quantum chemical and MM-approach to theendo/exoselectivity of diels-alder reactions in polar media

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
53
Issue
1
Identifiers
DOI: 10.1016/s0040-4020(96)00957-x
Disciplines
  • Chemistry
  • Physics

Abstract

Abstract The endo/exo selectivity of Diels-Alder reactions in water and methanol is studied with semiempirical methods using the SCRF approach and a combined quantum chemical (transition state) and molecular mechanics (solvent molecules) method (QC/MM) to determine the effect of protic solvents on the transition state energies. Evidently, the number of hydrogen bonds that causes strong Coulomb interaction, discriminates heats of formation of transition states. The results indicate that the s-cis/s-trans conformation of acrylates controls the endo/exo selectivity.

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