Unexpected Acid Catalysis in Reactions of Peroxyl Radicals with Phenols | Zendy

Valgimigli Luca | Zendy; Amorati Riccardo | Zendy; Petrucci Silvia | Zendy; Pedulli Gian Franco | Zendy; Hu Di | Zendy; Hanthorn Jason J. | Zendy; Pratt Derek A. | Zendy

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Unexpected Acid Catalysis in Reactions of Peroxyl Radicals with Phenols

Author(s) -

Valgimigli Luca,

Amorati Riccardo,

Petrucci Silvia,

Pedulli Gian Franco,

Hu Di,

Hanthorn Jason J.,

Pratt Derek A.

Publication year - 2009

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200903360

Subject(s) - chemistry , radical , reactivity (psychology) , catalysis , phenols , photochemistry , phenol , counterintuitive , organic chemistry , medicine , alternative medicine , pathology , philosophy , epistemology

Weak organic acids in millimolar concentrations increase the reactivity of peroxyl radicals with common phenolic antioxidants dramatically. This counterintuitive phenomenon relies on a substantially different reaction mechanism from that in the absence of an acid: rate‐determining electron transfer occurs from the hydrogen‐bonded phenol to the hydroperoxide cation radical present in equilibrium with the peroxyl radical under these conditions (see scheme).

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