Journal of the American Chemical Society p. 1666 - 1671 (1982)
Update date:2022-08-10
Topics:
Richter, Helen W.
Fetrow, Melanie A.
Lewis, Rachel E.
Waddell, Walter H.
Thre hydroxylation of benzoic acid induced by the aqueous chemical system composed of 5-methylphenazinium methyl sulfate, reduced β-nicotinamide adenine dinucleotide (NADH), and dissolved oxygen has been investigated.A quantitative determination of the reaction products was made using high-pressure liquid chromatographic methods.The effect of reaction conditions and of additives on the products yields was examined.Results indicate that the species initiating hydroxylation is the hydroxyl radical, produced from a one-electron reduction of hydrogen peroxide in an adventitions-metal-ion catalyzed Fenton-type reaction.Hydrogen peroxide is thought to be produced directly by the transfer of a hydride ion from a fully reduced 5-methylphenazinium cation to molecular oxygen, not by the disproportionation of superoxide radicals.It ia apparent that superoxide radicals are produced to a very limited extent during reaction and do not contribute substantially to product formation.The sole function of NADH is the reduction of the 5-methylphenazinium cation.
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