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Issue 12, 1992
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A molecular orbital study on the reactivity of L-ascorbic acid towards OH radical

Abstract

The reaction between L-ascorbic acid (AAH2) and OH radical has been investigated theoretically. The addition site on AAH2 and AAH is found to be the olefinic carbon adjacent to the carbonyl group, with much more distinct selectivity for AAH. Dehydration is found to occur readily not from the neutral ˙OH adduct AAH2OH˙, but from the anion adduct, AAHOH˙, which leads to formation of the most probable key intermediate radical 17(ascorbate anion radical). The parent molecule of AAH2, triose reductone TRH2(2,3-dihydroxprop-2-enal), undergoes ˙OH addition and dehydration in a similar manner to AAH2. The addition site has been confirmed by comparison of MO energies for four possible transition states of the TRH2(ab initio and MNDO) and AAH2(MNDO) systems. The importance of the conjugate bases, AAH and TRH, for yielding the key radicals is suggested.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1992, 2221-2232
Article type
Paper

A molecular orbital study on the reactivity of L-ascorbic acid towards OH radical

Y. Abe, S. Okada, R. Nakao, T. Horii, H. Inoue, S. Taniguchi and S. Yamabe, J. Chem. Soc., Perkin Trans. 2, 1992, 2221
DOI: 10.1039/P29920002221

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