Abstract
Electron transfer processes in a series of pyrazole-2-in-5-ones (“pyrazolones-5”) and some of their thioanalogues are studied experimentally and theoretically for the first time. The electrochemical behavior of thiopyrazolones and oxygen analogues is found to differ. The effect the nature of the electrode, heteroatom, and substituents exerts on the redox potentials is established. Schemes of redox processes for the compounds studied in nonaqueous media are suggested. The schemes take account the ability of pyrazolones-5 to autoprotonation. Electrooxidation of 1-phenyl-3-methyl-4-benzoylpyrazole-2-in-5-one and its thioanalogues is shown to occur similarly to electroless oxidation with the formation of various dimers. It is established that, in the absence of active substituents during the electroreduction of compounds under study, the reaction center is the pyrazolone cycle, whose reduction does not involve decomposition of heterocyclic system.
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Toropchina, A.V., Yanilkin, V.V., Morozov, V.I. et al. Electron Transfer Reactions in Pyrazole-2-in-5-ones and Their Thioanalogues. Russian Journal of Electrochemistry 39, 1181–1196 (2003). https://doi.org/10.1023/B:RUEL.0000003444.21581.05
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DOI: https://doi.org/10.1023/B:RUEL.0000003444.21581.05