Chemistry of Superoxide Ion as Revealed by the Differential Oxidation of Arylpyruvates | Zendy

Jefford Charles W. | Zendy; Cadby Peter A. | Zendy

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Chemistry of Superoxide Ion as Revealed by the Differential Oxidation of Arylpyruvates

Author(s) -

Jefford Charles W.,

Cadby Peter A.

Publication year - 1979

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19790620615

Subject(s) - chemistry , nucleophile , benzoic acid , hydroquinone , superoxide , benzaldehyde , medicinal chemistry , ion , photochemistry , nucleophilic addition , organic chemistry , catalysis , enzyme

Superoxide ion apparently reacts with acidic substrates via species such as O 2 , HO 2 , O 2 − , HO 2 −and H 2 O 2 . Arylpyruvates give arylacetates and arylaldehydes indicating competing nucleophilic and free radical oxidation. Benzaldehyde is further oxidized by free radical and nucleophilic dioxygen species giving benzoic acid. p ‐Hydroxybenzaldehyde gives the corresponding benzoic acid which is best accounted for by HO 2 , since O 2 −and O 2 are without effect. Hydroquinone is also produced presumably by nucleophilic attack of HO 2 − . Replacement of the acidic hydrogen atoms by sodium changes the product distribution in accord with these findings.

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