Abstract
Kinetics and mechanism of the reaction of vegetable phenols (PhOH) with 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH•) in a polar aprotic solvent, dimethyl sulfoxide, were studied. The reaction of natural phenols with DPPH• in dimethyl sulfoxide occurs in two stages. In the first stage, a proton-coupled electron transfer (PCET) occurs from a PhOH molecule to DPPH• to give primary transformation products, phenoxyl radicals (PhO•) and diphenyl hydrazine (DPPH–H), and in the second, the hydrazyl radical is consumed in the reaction with PhO• transformation products, enolized dimers, which is confirmed by NMR spectroscopy. A relationship was revealed between the antiradical activity of phenols in the reaction with DPPH• (ln k) and the ionization potential of the phenolates being formed.
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Original Russian Text © N.I. Belaya, A.V. Belyi, A.I. Pomeshchenko, K.V. Glushchenko, 2015, published in Zhurnal Prikladnoi Khimii, 2015, Vol. 88, No. 7, pp. 1087–1094.
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Belaya, N.I., Belyi, A.V., Pomeshchenko, A.I. et al. Natural phenolic compounds in the reaction with a nitrogen-centered radical in an aprotic solvent. Russ J Appl Chem 88, 1178–1185 (2015). https://doi.org/10.1134/S1070427215070125
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DOI: https://doi.org/10.1134/S1070427215070125