COMBINED QUANTUM-CHEMICAL AND MM-APPROACH TO THE ENDO EXO SELECTIVITYOF DIELS-ALDER REACTIONS IN POLAR MEDIA/

Authors
SCHLACHTER I MATTAY J SUER J HOWELER U WURTHWEIN G WURTHWEIN EU
Citation
I. Schlachter et al., COMBINED QUANTUM-CHEMICAL AND MM-APPROACH TO THE ENDO EXO SELECTIVITYOF DIELS-ALDER REACTIONS IN POLAR MEDIA/, Tetrahedron, 53(1), 1997, pp. 119-132
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
1
Year of publication
1997
Pages
119 - 132
Database
ISI
SICI code
0040-4020(1997)53:1<119:CQAMTT>2.0.ZU;2-4
Abstract
The endolexo selectivity of Diels-alder reactions in water and methano l 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 so lvents on the transition slate energies. Evidently, the number of hydr ogen bonds that causes strong Coulomb interaction, discriminates heals of formation of transition stales. The results indicate that the s-ci s/s-trans conformation of acrylates controls the endolexo selectivity. Copyright (C) 1996 Elsevier Science Ltd