Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid

Abstract

Naphthalene oxidation with metal-oxygen intermediates is adifficult reaction in environmental and biological chemistry.H erein, we report that aM n IV bis(hydroxo) complex, which was fully characterized by various physicochemical methods,s uch as ESI-MS,U V/Vis,a nd EPR analysis, X-ray diffraction, and XAS,can be employed for the oxidation of naphthalene in the presence of acid to afford1 ,4-naphthoquinone.R edox titration of the Mn IV bis(hydroxo) complex gave ao ne-electron reduction potential of 1.09 V, which is the most positive potential for all reported nonheme Mn IV bis-(hydroxo) species as well as Mn IV oxoa nalogues.K inetic studies,including kinetic isotope effect analysis,suggest that the naphthalene oxidation occurs through ar ate-determining electron transfer process.