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]

Jeong, Donghyun; Yan, James J.; Noh, Hyeonju; Hedman, Britt; Hodgson, Keith O.; Solomon, Edward I.; Cho, Jaeheung

doi:10.1002/anie.201802641

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]

Journal Article · Fri Apr 27 00:00:00 EDT 2018 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201802641· OSTI ID:1469755

Jeong, Donghyun ^[1]; Yan, James J. ^[2]; Noh, Hyeonju ^[1]; Hedman, Britt ^[3]; Hodgson, Keith O. ^[4]; Solomon, Edward I. ^[4];

^[1]

DGIST, Daegu (Korea)
Stanford Univ., Stanford, CA (United States)
Stanford Synchrotron Radiation Lab., Menlo Park, CA (United States)
Stanford Univ., Stanford, CA (United States); Stanford Synchrotron Radiation Lab., Menlo Park, CA (United States)

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

View Accepted Manuscript (DOE)

View Accepted Manuscript (Publisher)

Cite

Export

Save

Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: 2017R1A2B4005441; DGIST R&D Program 18-BD-0403; 2016M3D3A01913243; GM-40392; P41GM103393; AC02-76SF00515

OSTI ID:: 1469755

Alternate ID(s):: OSTI ID: 1438278

Journal Information:: Angewandte Chemie (International Edition), Vol. 57, Issue 26; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 17 works

Citation information provided by
Web of Science

References (46)

Evidence for a Precursor Complex in CH Hydrogen Atom Transfer Reactions Mediated by a Manganese(IV) Oxo Complex Garcia-Bosch, Isaac; Company, Anna; Cady, Clyde W. Angewandte Chemie International Edition, Vol. 50, Issue 25 https://doi.org/10.1002/anie.201100907	journal	April 2011
Mutagenicity and Carcinogenicity of Nitroarenes and Their Sources in the Environment Tokiwa, Hiroshi; Ohnishi, Yoshinari; Rosenkranz, Herbert S. CRC Critical Reviews in Toxicology, Vol. 17, Issue 1 https://doi.org/10.3109/10408448609037070	journal	January 1986
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 Park, Jiyun; Lee, Yong-Min; Nam, Wonwoo Journal of the American Chemical Society, Vol. 135, Issue 13 https://doi.org/10.1021/ja311662w	journal	March 2013
Proton-Coupled Electron Transfer of Unsaturated Fatty Acids and Mechanistic Insight into Lipoxygenase Fukuzumi, Shunichi Helvetica Chimica Acta, Vol. 89, Issue 10 https://doi.org/10.1002/hlca.200690223	journal	October 2006
Equatorial Ligand Perturbations Influence the Reactivity of Manganese(IV)-Oxo Complexes Massie, Allyssa A.; Denler, Melissa C.; Cardoso, Luísa Thiara Angewandte Chemie International Edition, Vol. 56, Issue 15 https://doi.org/10.1002/anie.201612309	journal	March 2017
Efficient Epoxidation of Styrene Derivatives by a Nonheme Iron(IV)-Oxo Complex via Proton-Coupled Electron Transfer with Triflic Acid Park, Jiyun; Lee, Yong-Min; Ohkubo, Kei Inorganic Chemistry, Vol. 54, Issue 12 https://doi.org/10.1021/acs.inorgchem.5b00504	journal	May 2015
Structures of the high-valent metal-ion haem–oxygen intermediates in peroxidases, oxygenases and catalases Hersleth, Hans-Petter; Ryde, Ulf; Rydberg, Patrik Journal of Inorganic Biochemistry, Vol. 100, Issue 4 https://doi.org/10.1016/j.jinorgbio.2006.01.018	journal	April 2006
Changes in fatty acid composition in Pseudomonas putida and Pseudomonas stutzeri during naphthalene degradation Mrozik, Agnieszka; Łabużek, Sylwia; Piotrowska-Seget, Zofia Microbiological Research, Vol. 160, Issue 2 https://doi.org/10.1016/j.micres.2004.11.001	journal	April 2005
Combined Experimental and Theoretical Study on Aromatic Hydroxylation by Mononuclear Nonheme Iron(IV)−Oxo Complexes de Visser, Sam P.; Oh, Kyungeun; Han, Ah-Rim Inorganic Chemistry, Vol. 46, Issue 11 https://doi.org/10.1021/ic700462h	journal	May 2007
Proton-Promoted Oxygen Atom Transfer vs Proton-Coupled Electron Transfer of a Non-Heme Iron(IV)-Oxo Complex Park, Jiyun; Morimoto, Yuma; Lee, Yong-Min Journal of the American Chemical Society, Vol. 134, Issue 8 https://doi.org/10.1021/ja211641s	journal	February 2012
Accurate Oxidation Potentials of Benzene and Biphenyl Derivatives via Electron-Transfer Equilibria and Transient Kinetics Merkel, Paul B.; Luo, Pu; Dinnocenzo, Joseph P. The Journal of Organic Chemistry, Vol. 74, Issue 15 https://doi.org/10.1021/jo9011267	journal	August 2009
Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung Angewandte Chemie International Edition, Vol. 49, Issue 44 https://doi.org/10.1002/anie.201000819	journal	September 2010
The reactivity of the active metal oxo and hydroxo intermediates and their implications in oxidations Chen, Zhuqi; Yin, Guochuan Chemical Society Reviews, Vol. 44, Issue 5 https://doi.org/10.1039/C4CS00244J	journal	January 2015
Water as an Oxygen Source in the Generation of Mononuclear Nonheme Iron(IV) Oxo Complexes Lee, Yong-Min; Dhuri, Sunder N.; Sawant, Sarvesh C. Angewandte Chemie International Edition, Vol. 48, Issue 10 https://doi.org/10.1002/anie.200805670	journal	February 2009
Switchover of the Mechanism between Electron Transfer and Hydrogen-Atom Transfer for a Protonated Manganese(IV)-Oxo Complex by Changing Only the Reaction Temperature Jung, Jieun; Kim, Surin; Lee, Yong-Min Angewandte Chemie International Edition, Vol. 55, Issue 26 https://doi.org/10.1002/anie.201602460	journal	May 2016
Tuning Reactivity and Mechanism in Oxidation Reactions by Mononuclear Nonheme Iron(IV)-Oxo Complexes Nam, Wonwoo; Lee, Yong-Min; Fukuzumi, Shunichi Accounts of Chemical Research, Vol. 47, Issue 4 https://doi.org/10.1021/ar400258p	journal	February 2014
A structurally characterized monomeric Mn(IV) complex in a discrete N2O4 coordination environment Rajendiran, T. M.; Kampf, Jeff W.; Pecoraro, Vincent L. Inorganica Chimica Acta, Vol. 339 https://doi.org/10.1016/S0020-1693(02)00956-8	journal	November 2002
Crystal structure of ceric ammonium nitrate Beineke, Thomas A.; Delgaudio, J. Inorganic Chemistry, Vol. 7, Issue 4 https://doi.org/10.1021/ic50062a020	journal	April 1968
Multi-Electron Oxidation of Anthracene Derivatives by Nonheme Manganese(IV)-Oxo Complexes Sharma, Namita; Jung, Jieun; Lee, Yong-Min Chemistry - A European Journal, Vol. 23, Issue 29 https://doi.org/10.1002/chem.201700666	journal	May 2017
Steric and Electronic Influence on Proton-Coupled Electron-Transfer Reactivity of a Mononuclear Mn(III)-Hydroxo Complex Rice, Derek B.; Wijeratne, Gayan B.; Burr, Andrew D. Inorganic Chemistry, Vol. 55, Issue 16 https://doi.org/10.1021/acs.inorgchem.6b01217	journal	July 2016
New insights from spectroscopy into the structure/function relationships of lipoxygenases Solomon, Edward I.; Zhou, Jing; Neese, Frank Chemistry & Biology, Vol. 4, Issue 11 https://doi.org/10.1016/S1074-5521(97)90113-7	journal	November 1997
Tuning the reactivity of mononuclear nonheme manganese( iv )-oxo complexes by triflic acid Chen, Junying; Yoon, Heejung; Lee, Yong-Min Chemical Science, Vol. 6, Issue 6 https://doi.org/10.1039/C5SC00535C	journal	January 2015
Synthesis, Characterization, and Solution Properties of a Novel Cross-Bridged Cyclam Manganese(IV) Complex Having Two Terminal Hydroxo Ligands Yin, Guochuan; McCormick, James M.; Buchalova, Maria Inorganic Chemistry, Vol. 45, Issue 20 https://doi.org/10.1021/ic0521123	journal	October 2006
Rapid C–H Bond Activation by a Monocopper(III)–Hydroxide Complex Donoghue, Patrick J.; Tehranchi, Jacqui; Cramer, Christopher J. Journal of the American Chemical Society, Vol. 133, Issue 44 https://doi.org/10.1021/ja207882h	journal	November 2011
A Highly Reactive Mononuclear Non-Heme Manganese(IV)–Oxo Complex That Can Activate the Strong C–H Bonds of Alkanes Wu, Xiujuan; Seo, Mi Sook; Davis, Katherine M. Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja208523u	journal	December 2011
Hydrogen Atom Abstraction by a Mononuclear Ferric Hydroxide Complex: Insights into the Reactivity of Lipoxygenase Goldsmith, Christian R.; Stack, T. Daniel P. Inorganic Chemistry, Vol. 45, Issue 15 https://doi.org/10.1021/ic060621e	journal	July 2006
Equatorial Ligand Perturbations Influence the Reactivity of Manganese(IV)-Oxo Complexes Massie, Allyssa A.; Denler, Melissa C.; Cardoso, Luísa Thiara Angewandte Chemie, Vol. 129, Issue 15 https://doi.org/10.1002/ange.201612309	journal	March 2017
Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex Sawant, Sarvesh C.; Wu, Xiujuan; Cho, Jaeheung Angewandte Chemie, Vol. 122, Issue 44 https://doi.org/10.1002/ange.201000819	journal	September 2010
Mn K-Edge X-ray Absorption Studies of Oxo- and Hydroxo-manganese(IV) Complexes: Experimental and Theoretical Insights into Pre-Edge Properties Leto, Domenick F.; Jackson, Timothy A. Inorganic Chemistry, Vol. 53, Issue 12 https://doi.org/10.1021/ic5006902	journal	May 2014
Structure and mechanism of lipoxygenases Prigge, S. T.; Boyington, J. C.; Faig, M. Biochimie, Vol. 79, Issue 11 https://doi.org/10.1016/S0300-9084(97)83495-5	journal	November 1997
Understanding the Zero-Field Splitting of Mononuclear Manganese(II) Complexes from Combined EPR Spectroscopy and Quantum Chemistry Duboc, Carole; Collomb, Marie-Noëlle; Neese, Frank Applied Magnetic Resonance, Vol. 37, Issue 1-4 https://doi.org/10.1007/s00723-009-0085-4	journal	November 2009
Understanding the Selectivity of a Moderate Oxidation Catalyst: Hydrogen Abstraction by a Fully Characterized, Activated Catalyst, the Robust Dihydroxo Manganese(IV) Complex of a Bridged Cyclam Yin, Guochuan; Danby, Andrew M.; Kitko, David Journal of the American Chemical Society, Vol. 129, Issue 6 https://doi.org/10.1021/ja0673229	journal	February 2007
Water as an Oxygen Source in the Generation of Mononuclear Nonheme Iron(IV) Oxo Complexes Lee, Yong-Min; Dhuri, Sunder N.; Sawant, Sarvesh C. Angewandte Chemie, Vol. 121, Issue 10 https://doi.org/10.1002/ange.200805670	journal	February 2009
Formation, Characterization, and O–O Bond Activation of a Peroxomanganese(III) Complex Supported by a Cross-Clamped Cyclam Ligand Colmer, Hannah E.; Howcroft, Anthony W.; Jackson, Timothy A. Inorganic Chemistry, Vol. 55, Issue 5 https://doi.org/10.1021/acs.inorgchem.5b02398	journal	February 2016
Switchover of the Mechanism between Electron Transfer and Hydrogen‐Atom Transfer for a Protonated Manganese(IV)–Oxo Complex by Changing Only the Reaction Temperature Jung, Jieun; Kim, Surin; Lee, Yong‐Min Angewandte Chemie, Vol. 128, Issue 26 https://doi.org/10.1002/ange.201602460	journal	May 2016
Remarkable solvent effect on the yield and specificity of oxidation of naphthalene catalyzed by iron(III)porphyrins Khavasi, Hamid Reza; Hosseiny Davarani, S. Saeed; Safari, Nasser Journal of Molecular Catalysis A: Chemical, Vol. 188, Issue 1-2 https://doi.org/10.1016/S1381-1169(02)00354-0	journal	September 2002
Hydrogen Atom Abstraction from Hydrocarbons by a Copper(III)-Hydroxide Complex Dhar, Debanjan; Tolman, William B. Journal of the American Chemical Society, Vol. 137, Issue 3 https://doi.org/10.1021/ja512014z	journal	January 2015
Multielectron Oxidation of Anthracenes with a One-Electron Oxidant via Water-Accelerated Electron-Transfer Disproportionation of the Radical Cations as the Rate-Determining Step Fukuzumi, Shunichi; Nakanishi, Ikuo; Tanaka, Keiko The Journal of Physical Chemistry A, Vol. 103, Issue 50 https://doi.org/10.1021/jp990541e	journal	December 1999
Bio-inspired arenecis-dihydroxylation by a non-haem iron catalyst modeling the action of naphthalene dioxygenase Feng, Yan; Ke, Chun-yen; Xue, Genqiang Chem. Commun., Issue 1 https://doi.org/10.1039/B817222F	journal	January 2008
Oxidative Reactivity Difference among the Metal Oxo and Metal Hydroxo Moieties: pH Dependent Hydrogen Abstraction by a Manganese(IV) Complex Having Two Hydroxide Ligands Yin, Guochuan; Danby, Andrew M.; Kitko, David Journal of the American Chemical Society, Vol. 130, Issue 48 https://doi.org/10.1021/ja804305x	journal	December 2008
A simple synthetic route to N,N′-dialkyl-2,11-diaza[3.3](2,6)-pyridinophanes. Crystal structures of N,N′-di-tert-butyl-2,11-diaza[3.3](2,6)pyridinophane and its copper(II) complex Che, Chi-Ming; Li, Zao-Ying; Wong, Kwok-Yin Polyhedron, Vol. 13, Issue 5 https://doi.org/10.1016/S0277-5387(00)81683-6	journal	January 1994
Preparation and Properties of a Monomeric Mn ^IV −Oxo Complex Parsell, Trenton H.; Behan, Rachel K.; Green, Michael T. Journal of the American Chemical Society, Vol. 128, Issue 27 https://doi.org/10.1021/ja062332v	journal	July 2006
Crystal Structure of Naphthalene Dioxygenase: Side-on Binding of Dioxygen to Iron Karlsson, A. Science, Vol. 299, Issue 5609 https://doi.org/10.1126/science.1078020	journal	February 2003
Active transition metal oxo and hydroxo moieties in nature's redox, enzymes and their synthetic models: Structure and reactivity relationships Yin, Guochuan Coordination Chemistry Reviews, Vol. 254, Issue 15-16 https://doi.org/10.1016/j.ccr.2010.01.016	journal	August 2010
Evidence for a Precursor Complex in CH Hydrogen Atom Transfer Reactions Mediated by a Manganese(IV) Oxo Complex Garcia-Bosch, Isaac; Company, Anna; Cady, Clyde W. Angewandte Chemie, Vol. 123, Issue 25 https://doi.org/10.1002/ange.201100907	journal	April 2011
Proton-Coupled Electron Transfer of Unsaturated Fatty Acids and Mechanistic Insight into Lipoxygenase Fukuzumi, Shunichi ChemInform, Vol. 38, Issue 4 https://doi.org/10.1002/chin.200704245	journal	January 2007

Linked Research (2)

Similar Records

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

Journal Article · Tue May 22 00:00:00 EDT 2018 · Angewandte Chemie · OSTI ID:1469755

Jeong, Donghyun; Yan, James J.; Noh, Hyeonju; +4 more

Tuning the reactivity of mononuclear nonheme manganese(iv)-oxo complexes by triflic acid

Journal Article · Tue Apr 14 00:00:00 EDT 2015 · Chemical Science · OSTI ID:1469755

Chen, Junying; Yoon, Heejung; Lee, Yong -Min; +4 more

A High‐Valent Non‐Heme μ‐Oxo Manganese(IV) Dimer Generated from a Thiolate‐Bound Manganese(II) Complex and Dioxygen

Journal Article · Fri Jun 09 00:00:00 EDT 2017 · Angewandte Chemie · OSTI ID:1469755

Brazzolotto, Deborah; Cantú Reinhard, Fabián G.; Smith‐Jones, Julian; +8 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
manganese
metal–hydroxo compounds
naphthalene
oxidation
reaction mechanisms

CCDC 1813763: Experimental Crystal Structure Determination: JIFLOC : [3,11-di-t-butyl-3,11,17,18-tetra-azatricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene]-dihydroxy-manganese(iv) hexakis[nitrato]-cerium(iv) Jeong, Donghyun; Yan, James J.; Noh, Hyeonju https://doi.org/10.5517/ccdc.csd.cc1ywchp The current record is supplemented by this dataset	dataset	December 2017
CCDC 1814153: Experimental Crystal Structure Determination: JIFLUI : [3,11-di-t-butyl-3,11,17,18-tetra-azatricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene]-bis(trifluoromethanesulfonato)-manganese(ii) Jeong, Donghyun; Yan, James; Noh, Hyeonju https://doi.org/10.5517/ccdc.csd.cc1yws2p The current record is supplemented by this dataset	dataset	December 2017

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]

Citation Formats

References (46)

Linked Research (2)

Similar Records

Related Subjects