Kinetics of the Oxidation of Quercetin by 2,2-Diphenyl-1-picrylhydrazyl (dpph•) | Zendy

Mario C. Foti | Zendy; Carmelo Daquino | Zendy; Gino A. DiLabio | Zendy; K. U. Ingold | Zendy

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Kinetics of the Oxidation of Quercetin by 2,2-Diphenyl-1-picrylhydrazyl (dpph^•)

Author(s) -

Mario C. Foti,

Carmelo Daquino,

Gino A. DiLabio,

K. U. Ingold

Publication year - 2011

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol2019086

Subject(s) - chemistry , quercetin , kinetics , dpph , medicinal chemistry , organic chemistry , nuclear chemistry , antioxidant , physics , quantum mechanics

In methanol/water, dpph(•) bleaching (519 nm) by quercetin, QH(2), exhibits biphasic kinetics. The dpph(•) reacts completely with the quercetin anion within 100 ms. Subsequent slower bleaching involves solvent and QH(2) addition to quinoid products. The fast reaction is first-order in dpph(•) but only ca. 0.38 order in [QH(2)]. This extraordinary nonintegral order is attributed to reversible formation of π-stacked {QH(-)/dpph(•)} complexes in which electron transfer to products, {QH(•)/dpph(-)}, is slow (k(ET) ≈ 10(5) s(-1)).

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