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Kinetic analysis of the disproportionation of aqueous glyoxal

✍ Scribed by Alfred R. Fratzke; Peter J. Reilly

Publisher: John Wiley and Sons
Year: 1986
Tongue: English
Weight: 704 KB
Volume: 18
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550180704

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✦ Synopsis

Rates of disproportionation of 0.015-0.4 mM aqueous glyoxal to glycolic acid were measured a t 0.24-75 mM NaOH and constant ionic strength, leading to the empirical rate expression r = (aJOH-1 + a,[OH~l')[GTl/(l + aJOH 11, where [GTl is the total glyoxal concentration. These results were confirmed in bicarbonatekarbonate buffer and at 2-20 mM [GTl. The rate form is in contradiction to earlier work on glyoxal, which suggested a second-order dependence on [OH 1, but agrees with the rate equation for phenylglyoxal disproportionation. The kinetic data can be explained by a mechanism postulating the presence of monohydrated and dihydrated forms of glyoxal in equilibrium, with the rate-limiting steps being intramolecular hydride ion transfers to the unhydrated carbonyl carbon of the mono-and divalent anions of glyoxal monohydrate.

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