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Mutual Activation of Two Radical Trapping Agents: Unusual “Win–Win Synergy” of Resveratrol and TEMPO during Scavenging of dpph• Radical in Methanol

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cris.lastimport.scopus2024-02-12T20:26:10Z
dc.abstract.enThe reaction of the 2,2′-diphenyl-1-picrylhydrazyl radical (dpph•) with resveratrol in methanol (kMeOH = 192 M–1 s–1) is greatly accelerated in the presence of stable nitroxyl radical TEMPO• (kmixMeOH = 1.4 × 103 M–1 s–1). This synergistic effect is surprising because TEMPO• alone reacts with dpph• relatively slowly (kS = 31 M–1 s–1 in methanol and 0.03 M–1 s–1 in nonpolar ethyl acetate). We propose a putative mechanism in which a mutual activation occurs within the acid–base pair TEMPO•/RSV to the resveratrol (RSV) anion and TEMPOH•+ radical cation, both being extremely fast scavengers of the dpph• radical. The fast initial reaction is followed by a much slower but continuous decay of dpph• because a nitroxyl radical is recovered from the TEMPOnium cation, which is reduced directly by RSV/RSV– to TEMPO• or recovered indirectly via a reaction with methanol, producing TEMPOH subsequently oxidized by dpph• to TEMPO•
dc.affiliationUniwersytet Warszawski
dc.contributor.authorLitwinienko, Grzegorz
dc.contributor.authorKonopko, Adrian
dc.date.accessioned2024-01-25T13:22:57Z
dc.date.available2024-01-25T13:22:57Z
dc.date.copyright2022-11-18
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number22
dc.description.versionFINAL_PUBLISHED
dc.description.volume87
dc.identifier.doi10.1021/ACS.JOC.2C02080
dc.identifier.issn0022-3263
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/113177
dc.identifier.weblinkhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c02080
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.pages15530-15538
dc.rightsCC-BY
dc.sciencecloudnosend
dc.titleMutual Activation of Two Radical Trapping Agents: Unusual “Win–Win Synergy” of Resveratrol and TEMPO during Scavenging of dpph• Radical in Methanol
dc.typeJournalArticle
dspace.entity.typePublication