Literature DB >> 21846127

Kinetics of the oxidation of quercetin by 2,2-diphenyl-1-picrylhydrazyl (dpph•).

Mario C Foti1, Carmelo Daquino, Gino A DiLabio, K U Ingold.   

Abstract

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)).
© 2011 American Chemical Society

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Year:  2011        PMID: 21846127     DOI: 10.1021/ol2019086

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

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