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Hydrogen and Proton Exchange at Carbon.Imbalanced Transition State and Mechanism Crossover

Abstract

A recent remarkable study of the C-H oxidation of substituted fluorenyl-benzoates together with the transfer of the proton to an internal receiving group by means of electron transfer outer-sphere oxidants, in the noteworthy absence of hydrogen-bonding interactions, is taken as example to uncover the existence of a mechanism crossover, making the reaction pass from a CPET pathway to a PTET pathway as the driving force of the global reaction decreases. This was also the occasion to stress that considerations based on “imbalanced” or “asynchronous” transitions states cannot replace activation/ driving force models based on quantum mechanical treatment of both electron and transferring proton.

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Publication details

The article was received on 11 Oct 2019, accepted on 29 Nov 2019 and first published on 29 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC05147C
Chem. Sci., 2020, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Hydrogen and Proton Exchange at Carbon.Imbalanced Transition State and Mechanism Crossover

    C. Costentin and J. Saveant, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/C9SC05147C

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