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Updated: Aug 17, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
Published on: July 19, 2019
Control of proton transfer: intramolecular vs intermolecular
Howard E Zimmerman1, Jie Cheng
1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA. zimmerman@chem.wisc.edu
Abstract:
[reaction: see text] Proton transfer in ketonization of enolates is a critical step in a myriad of organic reactions. Its stereochemistry has been the object of our studies since we reported kinetic protonation from the less hindered face of the molecule under kinetic control some decades ago. Very recently, we have succeeded in reversing the stereochemistry using 2-pyridyl groups to deliver the proton. We now report intramolecular delivery by other moieties and control of intramolecular versus intermolecular proton delivery.
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