Electrochemical behavior of carbonyl compounds and aci-reductones in relation to electron transport in biological processes: Rhodizonic acid and its reduction product in aqueous acid media*

Add time:08/30/2019    Source:sciencedirect.com

SummaryThe tetrahydroxy-1,4-benzoquinone(THQ)/rhodizonic acid (RDZ) redox system exhibits a reversible electrochemical behavior in neutral and basic media where the rhodizonate dianion RDZ2− predominates. In acid media, where the unionized diacid RDZ is dihydrated (RDZ, 2H2O), THQ is oxidized according to an E.C. mechanism: reversible oxidation of THQ yielding RDZ2−, followed by a pseudo first order hydration reaction (rate constant k=(8±3)×105×[H+]2 s−1). RDZ, 2H2O is reduced according to an E.C.E.1 mechanism: irreversible reduction of RDZ, 2H2O yielding monohydrated THQ (THQ, H2O) without preceding dehydration of the hydrated carbonyl groups, dehydration of THQ, H2O (rate constant k=(145±7)×[H+] s−1), reversible reduction of THQ producing hexahydroxybenzene (HHB). THQ, H2O itself appears to be irreversibly reducible in order to yield HHB at a sufficiently negative potential.

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