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Title: Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]

Abstract

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. Here, kinetic studies, including kinetic isotope effect analysis, suggest that the naphthalene oxidation occurs through a rate–determining electron transfer process.

Authors:
 [1];  [2];  [1];  [3];  [4];  [4]; ORCiD logo [1]
  1. DGIST, Daegu (Korea)
  2. Stanford Univ., Stanford, CA (United States)
  3. Stanford Synchrotron Radiation Lab., Menlo Park, CA (United States)
  4. Stanford Univ., Stanford, CA (United States); Stanford Synchrotron Radiation Lab., Menlo Park, CA (United States)
Publication Date:
Research Org.:
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1469755
Alternate Identifier(s):
OSTI ID: 1438278
Grant/Contract Number:  
2017R1A2B4005441; DGIST R&D Program 18-BD-0403; 2016M3D3A01913243; GM-40392; P41GM103393; AC02-76SF00515
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 57; Journal Issue: 26; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; manganese; metal–hydroxo compounds; naphthalene; oxidation; reaction mechanisms

Citation Formats

Jeong, Donghyun, Yan, James J., Noh, Hyeonju, Hedman, Britt, Hodgson, Keith O., Solomon, Edward I., and Cho, Jaeheung. Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]. United States: N. p., 2018. Web. doi:10.1002/anie.201802641.
Jeong, Donghyun, Yan, James J., Noh, Hyeonju, Hedman, Britt, Hodgson, Keith O., Solomon, Edward I., & Cho, Jaeheung. Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]. United States. doi:10.1002/anie.201802641.
Jeong, Donghyun, Yan, James J., Noh, Hyeonju, Hedman, Britt, Hodgson, Keith O., Solomon, Edward I., and Cho, Jaeheung. Fri . "Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]". United States. doi:10.1002/anie.201802641. https://www.osti.gov/servlets/purl/1469755.
@article{osti_1469755,
title = {Oxidation of Naphthalene with a Manganese(IV) Bis(hydroxo) Complex in the Presence of Acid [Naphthalene Oxidation of Manganese(IV)-Bis(Hydroxo) Complex in the Presence of Acid]},
author = {Jeong, Donghyun and Yan, James J. and Noh, Hyeonju and Hedman, Britt and Hodgson, Keith O. and Solomon, Edward I. and Cho, Jaeheung},
abstractNote = {Naphthalene oxidation with metal–oxygen intermediates is a difficult reaction in environmental and biological chemistry. Herein, we report that a MnIV 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 MnIV bis(hydroxo) complex gave a one–electron reduction potential of 1.09 V, which is the most positive potential for all reported nonheme MnIV bis(hydroxo) species as well as MnIV oxo analogues. Here, kinetic studies, including kinetic isotope effect analysis, suggest that the naphthalene oxidation occurs through a rate–determining electron transfer process.},
doi = {10.1002/anie.201802641},
journal = {Angewandte Chemie (International Edition)},
number = 26,
volume = 57,
place = {United States},
year = {2018},
month = {4}
}

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Cited by: 1 work
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  • Angewandte Chemie, Vol. 123, Issue 25
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    Works referencing / citing this record:

    Water as an Oxygen Source in the Generation of Mononuclear Nonheme Iron(IV) Oxo Complexes
    journal, February 2009

    • Lee, Yong-Min; Dhuri, Sunder N.; Sawant, Sarvesh C.
    • Angewandte Chemie, Vol. 121, Issue 10
    • DOI: 10.1002/ange.200805670

    Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex
    journal, September 2010

    • Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung
    • Angewandte Chemie, Vol. 122, Issue 44
    • DOI: 10.1002/ange.201000819

    Evidence for a Precursor Complex in CH Hydrogen Atom Transfer Reactions Mediated by a Manganese(IV) Oxo Complex
    journal, April 2011

    • Garcia-Bosch, Isaac; Company, Anna; Cady, Clyde W.
    • Angewandte Chemie, Vol. 123, Issue 25
    • DOI: 10.1002/ange.201100907

    Equatorial Ligand Perturbations Influence the Reactivity of Manganese(IV)-Oxo Complexes
    journal, March 2017

    • Massie, Allyssa A.; Denler, Melissa C.; Cardoso, Luísa Thiara
    • Angewandte Chemie, Vol. 129, Issue 15
    • DOI: 10.1002/ange.201612309

    Water as an Oxygen Source in the Generation of Mononuclear Nonheme Iron(IV) Oxo Complexes
    journal, February 2009

    • Lee, Yong-Min; Dhuri, Sunder N.; Sawant, Sarvesh C.
    • Angewandte Chemie International Edition, Vol. 48, Issue 10
    • DOI: 10.1002/anie.200805670

    Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex
    journal, September 2010

    • Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung
    • Angewandte Chemie International Edition, Vol. 49, Issue 44
    • DOI: 10.1002/anie.201000819

    Evidence for a Precursor Complex in CH Hydrogen Atom Transfer Reactions Mediated by a Manganese(IV) Oxo Complex
    journal, April 2011

    • Garcia-Bosch, Isaac; Company, Anna; Cady, Clyde W.
    • Angewandte Chemie International Edition, Vol. 50, Issue 25
    • DOI: 10.1002/anie.201100907

    Switchover of the Mechanism between Electron Transfer and Hydrogen-Atom Transfer for a Protonated Manganese(IV)-Oxo Complex by Changing Only the Reaction Temperature
    journal, May 2016

    • Jung, Jieun; Kim, Surin; Lee, Yong-Min
    • Angewandte Chemie International Edition, Vol. 55, Issue 26
    • DOI: 10.1002/anie.201602460

    Equatorial Ligand Perturbations Influence the Reactivity of Manganese(IV)-Oxo Complexes
    journal, March 2017

    • Massie, Allyssa A.; Denler, Melissa C.; Cardoso, Luísa Thiara
    • Angewandte Chemie International Edition, Vol. 56, Issue 15
    • DOI: 10.1002/anie.201612309

    Multi-Electron Oxidation of Anthracene Derivatives by Nonheme Manganese(IV)-Oxo Complexes
    journal, May 2017

    • Sharma, Namita; Jung, Jieun; Lee, Yong-Min
    • Chemistry - A European Journal, Vol. 23, Issue 29
    • DOI: 10.1002/chem.201700666

    Proton-Coupled Electron Transfer of Unsaturated Fatty Acids and Mechanistic Insight into Lipoxygenase
    journal, October 2006


    Understanding the Zero-Field Splitting of Mononuclear Manganese(II) Complexes from Combined EPR Spectroscopy and Quantum Chemistry
    journal, November 2009

    • Duboc, Carole; Collomb, Marie-Noëlle; Neese, Frank
    • Applied Magnetic Resonance, Vol. 37, Issue 1-4
    • DOI: 10.1007/s00723-009-0085-4

    Structures of the high-valent metal-ion haem–oxygen intermediates in peroxidases, oxygenases and catalases
    journal, April 2006


    Changes in fatty acid composition in Pseudomonas putida and Pseudomonas stutzeri during naphthalene degradation
    journal, April 2005

    • Mrozik, Agnieszka; Łabużek, Sylwia; Piotrowska-Seget, Zofia
    • Microbiological Research, Vol. 160, Issue 2
    • DOI: 10.1016/j.micres.2004.11.001

    Formation, Characterization, and O–O Bond Activation of a Peroxomanganese(III) Complex Supported by a Cross-Clamped Cyclam Ligand
    journal, February 2016


    Steric and Electronic Influence on Proton-Coupled Electron-Transfer Reactivity of a Mononuclear Mn(III)-Hydroxo Complex
    journal, July 2016


    Tuning Reactivity and Mechanism in Oxidation Reactions by Mononuclear Nonheme Iron(IV)-Oxo Complexes
    journal, February 2014

    • Nam, Wonwoo; Lee, Yong-Min; Fukuzumi, Shunichi
    • Accounts of Chemical Research, Vol. 47, Issue 4
    • DOI: 10.1021/ar400258p

    Synthesis, Characterization, and Solution Properties of a Novel Cross-Bridged Cyclam Manganese(IV) Complex Having Two Terminal Hydroxo Ligands
    journal, October 2006

    • Yin, Guochuan; McCormick, James M.; Buchalova, Maria
    • Inorganic Chemistry, Vol. 45, Issue 20
    • DOI: 10.1021/ic0521123

    Hydrogen Atom Abstraction by a Mononuclear Ferric Hydroxide Complex:  Insights into the Reactivity of Lipoxygenase
    journal, July 2006

    • Goldsmith, Christian R.; Stack, T. Daniel P.
    • Inorganic Chemistry, Vol. 45, Issue 15
    • DOI: 10.1021/ic060621e

    Crystal structure of ceric ammonium nitrate
    journal, April 1968

    • Beineke, Thomas A.; Delgaudio, J.
    • Inorganic Chemistry, Vol. 7, Issue 4
    • DOI: 10.1021/ic50062a020

    Combined Experimental and Theoretical Study on Aromatic Hydroxylation by Mononuclear Nonheme Iron(IV)−Oxo Complexes
    journal, May 2007

    • de Visser, Sam P.; Oh, Kyungeun; Han, Ah-Rim
    • Inorganic Chemistry, Vol. 46, Issue 11
    • DOI: 10.1021/ic700462h

    Preparation and Properties of a Monomeric Mn IV −Oxo Complex
    journal, July 2006

    • Parsell, Trenton H.; Behan, Rachel K.; Green, Michael T.
    • Journal of the American Chemical Society, Vol. 128, Issue 27
    • DOI: 10.1021/ja062332v

    Rapid C–H Bond Activation by a Monocopper(III)–Hydroxide Complex
    journal, November 2011

    • Donoghue, Patrick J.; Tehranchi, Jacqui; Cramer, Christopher J.
    • Journal of the American Chemical Society, Vol. 133, Issue 44
    • DOI: 10.1021/ja207882h

    A Highly Reactive Mononuclear Non-Heme Manganese(IV)–Oxo Complex That Can Activate the Strong C–H Bonds of Alkanes
    journal, December 2011

    • Wu, Xiujuan; Seo, Mi Sook; Davis, Katherine M.
    • Journal of the American Chemical Society, Vol. 133, Issue 50
    • DOI: 10.1021/ja208523u

    Proton-Promoted Oxygen Atom Transfer vs Proton-Coupled Electron Transfer of a Non-Heme Iron(IV)-Oxo Complex
    journal, February 2012

    • Park, Jiyun; Morimoto, Yuma; Lee, Yong-Min
    • Journal of the American Chemical Society, Vol. 134, Issue 8
    • DOI: 10.1021/ja211641s

    Brønsted Acid-Promoted C–H Bond Cleavage via Electron Transfer from Toluene Derivatives to a Protonated Nonheme Iron(IV)-Oxo Complex with No Kinetic Isotope Effect
    journal, March 2013

    • Park, Jiyun; Lee, Yong-Min; Nam, Wonwoo
    • Journal of the American Chemical Society, Vol. 135, Issue 13
    • DOI: 10.1021/ja311662w

    Hydrogen Atom Abstraction from Hydrocarbons by a Copper(III)-Hydroxide Complex
    journal, January 2015

    • Dhar, Debanjan; Tolman, William B.
    • Journal of the American Chemical Society, Vol. 137, Issue 3
    • DOI: 10.1021/ja512014z

    Oxidative Reactivity Difference among the Metal Oxo and Metal Hydroxo Moieties: pH Dependent Hydrogen Abstraction by a Manganese(IV) Complex Having Two Hydroxide Ligands
    journal, December 2008

    • Yin, Guochuan; Danby, Andrew M.; Kitko, David
    • Journal of the American Chemical Society, Vol. 130, Issue 48
    • DOI: 10.1021/ja804305x

    Accurate Oxidation Potentials of Benzene and Biphenyl Derivatives via Electron-Transfer Equilibria and Transient Kinetics
    journal, August 2009

    • Merkel, Paul B.; Luo, Pu; Dinnocenzo, Joseph P.
    • The Journal of Organic Chemistry, Vol. 74, Issue 15
    • DOI: 10.1021/jo9011267

    Multielectron Oxidation of Anthracenes with a One-Electron Oxidant via Water-Accelerated Electron-Transfer Disproportionation of the Radical Cations as the Rate-Determining Step
    journal, December 1999

    • Fukuzumi, Shunichi; Nakanishi, Ikuo; Tanaka, Keiko
    • The Journal of Physical Chemistry A, Vol. 103, Issue 50
    • DOI: 10.1021/jp990541e

    Crystal Structure of Naphthalene Dioxygenase: Side-on Binding of Dioxygen to Iron
    journal, February 2003


    Mutagenicity and Carcinogenicity of Nitroarenes and Their Sources in the Environment
    journal, January 1986

    • Tokiwa, Hiroshi; Ohnishi, Yoshinari; Rosenkranz, Herbert S.
    • CRC Critical Reviews in Toxicology, Vol. 17, Issue 1
    • DOI: 10.3109/10408448609037070