Oxidation of hydroquinones by a nonheme iron(IV)-oxo species

Kasi Nehru, Yukyeong Jang, Sunok Oh, Frédéric Dallemer, Wonwoo Nam, Jinheung Kim

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The reactivity of an isolated, well-characterized nonheme iron(IV)-oxo complex, [(TMC)FeIV{double bond, long}O]2+ (TMC = 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane), has been examined in the oxidation of hydroquinones. This complex has been shown to oxidize a series of hydroquinones, resulting in the production of the corresponding quinone products. Kinetic studies performed with substituted hydroquinones revealed a good correlation between reaction rates of the iron(IV)-oxo complex and the electron-donating ability of the substituents and the bond dissociation energy (BDE) of substrate O-H bonds. These results with a kinetic isotope effect (KIE) of 2.7 led us to propose a hydrogen-atom abstraction mechanism for the oxidation of hydroquinones by the nonheme iron(IV)-oxo species.

Original languageEnglish
Pages (from-to)2557-2561
Number of pages5
JournalInorganica Chimica Acta
Issue number8
StatePublished - 2 Jun 2008

Bibliographical note

Funding Information:
This work was supported by the SRC/ERC program of MOST/KOSEF (R11-2005-008-000-0 to J.K.), Seoul R& BD program (to J.K.), STAR program (2005–2007 to J.K. and F.D.), and the Ministry of Science and Technology of Korea through Creative Research Initiative Program (to W.N.).


  • High-valent iron-oxo species
  • Hydrogen-atom abstraction
  • Hydroquinone
  • Nonheme iron enzymes
  • Oxidation


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