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Issue 7, 1983
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Radical-induced oxidation of pyridazine-3,6-diol (maleic hydrazide). A model for chemiluminescent cyclic hydrazides

Abstract

Oxidative radicals such as N˙–3, CO˙–3, (SCN)˙–2 and Br˙–2 oxidize the basic form of maleic hydrazide (MH) to the corresponding diazasemiquinone radical. The acid (MH2) is resistant towards all oxidants tested. The diazasemiquinone radical has a pKa of 6.3 ± 0.1. Neither MH˙ nor M˙– react with molecular oxygen. Dismutation of M˙– results in the formation of the diazaquinone (M), which is extremely reactive towards nucleophiles. In particular it forms maleic acid with HO2. The radical M˙– combines with O˙–2 to yield maleic acid as well. Regeneration of maleic hydrazide in the reaction of M˙– with O˙–2 below pH 7.5 indicates pH-dependent reactivity of the intermediate hydroperoxide.

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Article type: Paper
DOI: 10.1039/F19837901493
Citation: J. Chem. Soc., Faraday Trans. 1, 1983,79, 1493-1501
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    Radical-induced oxidation of pyridazine-3,6-diol (maleic hydrazide). A model for chemiluminescent cyclic hydrazides

    T. E. Eriksen, J. Lind and G. Merényi, J. Chem. Soc., Faraday Trans. 1, 1983, 79, 1493
    DOI: 10.1039/F19837901493

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