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Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid
Author(s) -
Jeong Donghyun,
Yan James J.,
Noh Hyeonju,
Hedman Britt,
Hodgson Keith O.,
Solomon Edward I.,
Cho Jaeheung
Publication year - 2018
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.201802641
Subject(s) - chemistry , naphthalene , redox , manganese , electron paramagnetic resonance , electron transfer , inorganic chemistry , titration , radical , photochemistry , rhenium , medicinal chemistry , organic chemistry , physics , nuclear magnetic resonance
Naphthalene oxidation with metal–oxygen intermediates is a difficult reaction in environmental and biological chemistry. Herein, we report that a Mn IV bis(hydroxo) complex, which was fully characterized by various physicochemical methods, such as ESI‐MS, UV/Vis, and EPR analysis, X‐ray diffraction, and XAS, can be employed for the oxidation of naphthalene in the presence of acid to afford 1,4‐naphthoquinone. Redox titration of the Mn IV bis(hydroxo) complex gave a one‐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 oxo analogues. Kinetic studies, including kinetic isotope effect analysis, suggest that the naphthalene oxidation occurs through a rate‐determining electron transfer process.