Back to Search
Start Over
Mechanistic Insight on the Diels-Alder Reaction Catalyzed by a Self-Assembled Molecular Capsule.
- Source :
-
Journal of Organic Chemistry . 4/19/2013, Vol. 78 Issue 8, p3577-3582. 6p. - Publication Year :
- 2013
-
Abstract
- We combined Monte Carlo simulations and density functional theory calculations to study the mechanism of the Diels-Alder reaction of p-quinone and cyclohexadiene catalyzed by a self-assembled molecular capsule. Our calculations show that the encapsulation of the reactants into the cage is driven by hydrogen-bonding interactions and π-π stacking interactions between two reactants and the capsule. The encapsulated Diels-Alder reaction at different locations inside the capsule may have quite different reactivity due to different guest-host interactions. A comparison of the free energy profiles of the Diels-Alder reaction in the capsule and in the bulk solution reveals that the Diels-Alder reaction in the capsule is accelerated because the host-guest interaction leads to a relatively smaller barrier for the cycloaddition step. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 78
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 87528028
- Full Text :
- https://doi.org/10.1021/jo4000509