Characterization and Fate of Hydrogen-Bonded Free-Radical Intermediates and Their Coupling Products from the Hydrogen Atom Transfer Agent 1,8-Naphthalenediol.

ABSTRACT: 1,8-Naphthalenediol (dihydroxynaphthalene, 1,8-DHN) has been shown to be a potent hydrogen atom transfer (HAT) antioxidant compound because of the strong stabilization of the resulting free radical by intramolecular hydrogen bonding. However, the properties, reactivity, and fate of the 1,8-DHN phenoxyl radical have remained so far uncharted. Herein, we report an integrated experimental and computational characterization of the early intermediates and dimer products that arise by the oxidation of 1,8-DHN. Laser flash photolysis (LFP) studies of HAT from 1,8-DHN to the cumyloxyl and aminoxyl radicals showed the generation of a transient species absorbing at 350, 400, and >600 nm attributable to the 1,8-DHN phenoxyl radical. Peroxidase/H₂O₂ oxidation of 1,8-DHN was found

SUBMITTER: Manini P 

PROVIDER: S-EPMC6641764 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature