The reactivity of 5-[()-2-(4-hydroxyphenyl)ethen-1-yl]benzene-1,3-diol (-resveratrol) and related compounds toward electrogenerated superoxide radical anion (O) were investigated using electrochemistry, in situ electrolytic electron spin resonance, and in situ electrolytic ultraviolet-visible spectral measurements, in ,-dimethylformamide (DMF) with the aid of density functional theory (DFT) calculations. The quasi-reversible cyclic voltammogram of dioxygen/O was modified by the presence of -resveratrol, suggesting that the electrogenerated O was scavenged by -resveratrol through proton-coupled electron transfer (PCET) via three phenolic hydroxy groups (OH) on the stilbene moiety. The reactivity of -resveratrol toward O characterized by the OHs was experimentally confirmed in comparative analyses using some related compounds, pinosylvin, pterostilbene, -coumaric acid, and so on, in DMF. The electrochemical and DFT results suggested that a concerted PCET mechanism via 4'OH of -resveratrol proceeds, where the coplanarity of the two phenolic rings in the stilbene moiety linked by an ethylene bridge is essential for a successful O scavenging.
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