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Issue 11, 2011
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Pyridine as proton acceptor in the concerted protonelectron transferoxidation of phenol

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Abstract

Taking pyridine as a prototypal example of biologically important nitrogen bases involved in proton-coupled electron transfers, it is shown with the example of the photochemically triggered oxidation of phenol by RuIII(bpy)3 that this proton acceptor partakes in a concerted pathway whose kinetic characteristics can be extracted from the overall kinetic response. The treatment of these data, implemented by the results of a parallel study carried out in heavy water, allowed the determination of the intrinsic kinetic characteristics of this proton acceptor. Comparison of the reorganization energies and of the pre-exponential factors previously derived for hydrogen phosphate and water (in water) as proton acceptors suggests that, in the case of pyridine, the proton charge is delocalized over a primary shell of water molecules firmly bound to the pyridinium cation.

Graphical abstract: Pyridine as proton acceptor in the concerted proton electron transfer oxidation of phenol

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Article information


Submitted
17 Jan 2011
Accepted
29 Mar 2011
First published
29 Mar 2011

Org. Biomol. Chem., 2011,9, 4064-4069
Article type
Paper

Pyridine as proton acceptor in the concerted proton electron transfer oxidation of phenol

J. Bonin, C. Costentin, M. Robert and J. Savéant, Org. Biomol. Chem., 2011, 9, 4064
DOI: 10.1039/C1OB05090G

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