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An MM and QM Study of Biomimetic Catalysis of Diels-Adler Reactions Using Cyclodextrins

Wei Chen, Lipeng Sun, Zhiye Tang, Chia-en A. Chang
doi: https://doi.org/10.1101/169565
Wei Chen
1 Department of Chemistry, University of California, Riverside, CA92521
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Lipeng Sun
2 Illinois Rocstar LLC, P.O. Box 3001, Champaign, IL 61826
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Zhiye Tang
1 Department of Chemistry, University of California, Riverside, CA92521
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Chia-en A. Chang
1 Department of Chemistry, University of California, Riverside, CA92521
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  • For correspondence: chiaenc@ucr.edu
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Abstract

We performed computational research to investigate the mechanism by which cyclodextrins (CDs) catalyze Diels-Alder reactions between 9-anthracenemethanol and N-cyclohexylmaleimide. Hydrogen bonds (Hbonds) between N-cyclohexylmaleimide and the hydroxyl groups of cyclodextrins were suggested to play an important role in the catalysis.However, our free energy calculations and molecular dynamics simulations showed that these Hbonds are not stable, and quantum mechanics calculations suggested that the reaction is not promoted by these Hbonds. The binding of 9-anthracenemethanol and N-cyclohexylmaleimide to cyclodextrins was the key to the catalysis. Cyclodextrins act as a container to hold the two reactants in the cavity, pre-organizes them for the reactions, and thus reduces the entropy penalty to the activation free energy. Dimethyl-β-CD was a better catalyst for this specific reaction than β-CD because of its stronger van der Waals interaction with the pre-organized reactants and better performance in reducing the activation energy. This computational work sheds light on the mechanism of the catalytic reaction by cyclodextrins and introduces new perspectives of supramolecular catalysis.

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Posted September 24, 2017.
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An MM and QM Study of Biomimetic Catalysis of Diels-Adler Reactions Using Cyclodextrins
Wei Chen, Lipeng Sun, Zhiye Tang, Chia-en A. Chang
bioRxiv 169565; doi: https://doi.org/10.1101/169565
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An MM and QM Study of Biomimetic Catalysis of Diels-Adler Reactions Using Cyclodextrins
Wei Chen, Lipeng Sun, Zhiye Tang, Chia-en A. Chang
bioRxiv 169565; doi: https://doi.org/10.1101/169565

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