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Confinement induced catalytic activity in a Diels-Alder reaction: comparison among various CB[n], n = 6–8, cavitands
- Source :
- Journal of Molecular Modeling. 24
- Publication Year :
- 2018
- Publisher :
- Springer Science and Business Media LLC, 2018.
-
Abstract
- The impact of the size of the confining regime on the thermodynamic and kinetic outcome of a representative Diels-Alder reaction between ethylene and 1,3 butadiene has been investigated in silico. To this end, two organic hosts namely cucurbit[6]uril (CB[6]) and cucurbit[8]uril (CB[8]) have been considered in order to impose confinement on the reactants/transition state/product of the concerned reaction. The obtained results have been compared with the recently reported (Chakraborty et al. ChemPhysChem 18:2162-2170, 2017) corresponding case of the same reaction happening inside cucurbit[7]uril (CB[7]). Results indicate that as compared to the reaction of ethylene and 1,3 butadiene inside CB[7], both CB[6] and CB[8] cavitands slow down the same reaction at 298.15 K and 1 atm. It appears that the size of the cavitand plays a crucial role in affecting the kinetic outcome of the considered reaction. While CB[7] can enforce productive alignment of the reactants inside its cavity thereby facilitating the reaction, neither CB[6] nor CB[8] can perform the same task as effectively. This situation bears qualitative resemblance with the cases of enzyme catalyzed reactions.
- Subjects :
- Ethylene
Enzyme catalyzed
010405 organic chemistry
Chemistry
Organic Chemistry
Cavitand
010402 general chemistry
01 natural sciences
Medicinal chemistry
Catalysis
0104 chemical sciences
Computer Science Applications
Inorganic Chemistry
chemistry.chemical_compound
Computational Theory and Mathematics
Physical and Theoretical Chemistry
Diels–Alder reaction
Subjects
Details
- ISSN :
- 09485023 and 16102940
- Volume :
- 24
- Database :
- OpenAIRE
- Journal :
- Journal of Molecular Modeling
- Accession number :
- edsair.doi.dedup.....6e405c7593e7c5831bf4fcf395eb3ef3