Concerted proton-electron transfer oxidation of phenols and hydrocarbons by a high-valent nickel complex

Fisher, Katherine J.; Feuer, Margalit L.; Lant, Hannah M. C.; Mercado, Brandon Q.; Crabtree, Robert H.; Brudvig, Gary W.

doi:10.1039/c9sc05565g

Title: Concerted proton-electron transfer oxidation of phenols and hydrocarbons by a high-valent nickel complex

Journal Article · 06 January 2020 · Chemical Science

DOI: https://doi.org/10.1039/c9sc05565g · OSTI ID:1582476

Fisher, Katherine J. ^[1]; Feuer, Margalit L. ^[1]; Lant, Hannah M. C. ^[1]; Mercado, Brandon Q. ^[1];

^[1];

^[1]

Yale Univ., New Haven, CT (United States)

The high-valent nickel(III) complex Ni(pyalk)₂⁺ (2) was prepared by oxidation of a nickel(II) complex, Ni(pyalk)₂ (1) (pyalk = 2-pyridyl-2-propanoate). 2 and derivatives were fully characterized by mass spectrometry and X-ray crystallography. Electron paramagnetic resonance spectroscopy and X-ray photoelectron spectroscopy confirm that the oxidation is metal-centered. 2 was found to react with a variety of phenolic and hydrocarbon substrates. A linear correlation between the measured rate constant and the substrate bond dissociation enthalpy (BDE) was found for both phenolic and hydrocarbon substrates. Large H/D kinetic isotope effects were also observed for both sets of substrates. These results suggest that 2 reacts through concerted proton-electron transfer (CPET). Analysis of measured thermodynamic parameters allows us to calculate a bond dissociation free energy (BDFE) of ~91 kcal mol^–1 for the O–H bond of the bound pyalk ligand. These findings may shed light onto CPET steps in oxidative catalysis and have implications for ligand design in catalytic systems.

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Research Organization:: Northwestern Univ., Evanston, IL (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Light Energy Activated Redox Processes (LEAP)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001059; DGE1122492

OSTI ID:: 1582476

Alternate ID(s):: OSTI ID: 1624985

Journal Information:: Chemical Science, Vol. 11, Issue 6; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 12 works

Citation information provided by
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References (76)

Mechanism of Oxidation Reactions Catalyzed by Cytochrome P450 Enzymes Meunier, Bernard; de Visser, Samuël P.; Shaik, Sason Chemical Reviews, Vol. 104, Issue 9 https://doi.org/10.1021/cr020443g	journal	September 2004
Oxidizing species in the mechanism of cytochrome P450 Ortiz de Montellano, Paul R.; De Voss, James J. Natural Product Reports, Vol. 19, Issue 4 https://doi.org/10.1039/b101297p	journal	May 2002
Proton-Coupled Electron Transfer Weinberg, David R.; Gagliardi, Christopher J.; Hull, Jonathan F. Chemical Reviews, Vol. 112, Issue 7 https://doi.org/10.1021/cr200177j	journal	April 2012
Pivotal Role and Regulation of Proton Transfer in Water Oxidation on Hematite Photoanodes Zhang, Yuchao; Zhang, Hongna; Ji, Hongwei Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.5b12069	journal	February 2016
Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities Miller, David C.; Tarantino, Kyle T.; Knowles, Robert R. Topics in Current Chemistry, Vol. 374, Issue 3 https://doi.org/10.1007/s41061-016-0030-6	journal	May 2016
Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins Crossley, Steven W. M.; Obradors, Carla; Martinez, Ruben M. Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.6b00334	journal	June 2016
Nickel Superoxide Dismutase Structure and Mechanism ^† Barondeau, David P.; Kassmann, Carey J.; Bruns, Cami K. Biochemistry, Vol. 43, Issue 25 https://doi.org/10.1021/bi0496081	journal	June 2004
Use of a Metallopeptide-Based Mimic Provides Evidence for a Proton-Coupled Electron-Transfer Mechanism for Superoxide Reduction by Nickel-Containing Superoxide Dismutase Shearer, Jason Angewandte Chemie International Edition, Vol. 52, Issue 9 https://doi.org/10.1002/anie.201209746	journal	January 2013
Insight into the Structure and Mechanism of Nickel-Containing Superoxide Dismutase Derived from Peptide-Based Mimics Shearer, Jason Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500060s	journal	May 2014
A Pyridine Alkoxide Chelate Ligand That Promotes Both Unusually High Oxidation States and Water-Oxidation Catalysis Michaelos, Thoe K.; Shopov, Dimitar Y.; Sinha, Shashi Bhushan Accounts of Chemical Research, Vol. 50, Issue 4 https://doi.org/10.1021/acs.accounts.6b00652	journal	February 2017
Water-Nucleophilic Attack Mechanism for the Cu II (pyalk) 2 Water-Oxidation Catalyst Rudshteyn, Benjamin; Fisher, Katherine J.; Lant, Hannah M. C. ACS Catalysis, Vol. 8, Issue 9 https://doi.org/10.1021/acscatal.8b02466	journal	July 2018
Electrocatalytic Water Oxidation by a Water-Soluble Copper(II) Complex with a Copper-Bound Carbonate Group Acting as a Potential Proton Shuttle Chen, Fangfang; Wang, Ni; Lei, Haitao Inorganic Chemistry, Vol. 56, Issue 21 https://doi.org/10.1021/acs.inorgchem.7b02125	journal	October 2017
Characterization and Reactivity of a Terminal Nickel(III)-Oxygen Adduct Pirovano, Paolo; Farquhar, Erik R.; Swart, Marcel Chemistry - A European Journal, Vol. 21, Issue 9 https://doi.org/10.1002/chem.201406485	journal	January 2015
Water-soluble hexadentate Schiff-base ligands as sequestrating agents for iron(III) and gallium(III) Evans, Dennis F.; Jakubovic, David A. Journal of the Chemical Society, Dalton Transactions, Issue 12 https://doi.org/10.1039/dt9880002927	journal	January 1988
A Dinuclear Iridium(V,V) Oxo-Bridged Complex Characterized Using a Bulk Electrolysis Technique for Crystallizing Highly Oxidizing Compounds Shopov, Dimitar Y.; Sharninghausen, Liam S.; Sinha, Shashi Bhushan Inorganic Chemistry, Vol. 57, Issue 9 https://doi.org/10.1021/acs.inorgchem.8b00757	journal	April 2018
High Oxidation State Iridium Mono-μ-oxo Dimers Related to Water Oxidation Catalysis Sharninghausen, Liam S.; Sinha, Shashi Bhushan; Shopov, Dimitar Y. Journal of the American Chemical Society, Vol. 138, Issue 49 https://doi.org/10.1021/jacs.6b07716	journal	December 2016
Redox Activity of Oxo-Bridged Iridium Dimers in an N,O-Donor Environment: Characterization of Remarkably Stable Ir(IV,V) Complexes Sinha, Shashi Bhushan; Shopov, Dimitar Y.; Sharninghausen, Liam S. Journal of the American Chemical Society, Vol. 139, Issue 28 https://doi.org/10.1021/jacs.7b04874	journal	July 2017
Synthesis and Characterization of Iridium(V) Coordination Complexes With an N,O-Donor Organic Ligand Sharninghausen, Liam S.; Sinha, Shashi Bhushan; Shopov, Dimitar Y. Angewandte Chemie, Vol. 129, Issue 42 https://doi.org/10.1002/ange.201707593	journal	September 2017
EPR and electrochemical study of nickel(III) complexes of bis(3,5-dichlorosalicylaldehyde) o-phenylenediimine. Evidence for adduct formation with pyridines De Castro, Baltazar; Freire, Cristina Inorganic Chemistry, Vol. 29, Issue 25 https://doi.org/10.1021/ic00350a019	journal	December 1990
Tuning the Reactivity of Terminal Nickel(III)–Oxygen Adducts for C–H Bond Activation Pirovano, Paolo; Farquhar, Erik R.; Swart, Marcel Journal of the American Chemical Society, Vol. 138, Issue 43 https://doi.org/10.1021/jacs.6b08406	journal	October 2016
Hydrogen Atom Transfer by a High-Valent Nickel-Chloride Complex Mondal, Prasenjit; Pirovano, Paolo; Das, Ankita Journal of the American Chemical Society, Vol. 140, Issue 5 https://doi.org/10.1021/jacs.7b11953	journal	January 2018
Electrocatalytic Water Oxidation by a Copper(II) Complex of an Oxidation-Resistant Ligand Fisher, Katherine J.; Materna, Kelly L.; Mercado, Brandon Q. ACS Catalysis, Vol. 7, Issue 5 https://doi.org/10.1021/acscatal.7b00494	journal	April 2017
The first crystal structure of a monomeric phenoxyl radical: 2,4,6-tri-tert-butylphenoxyl radical Manner, Virginia W.; Markle, Todd F.; Freudenthal, John H. Chem. Commun., Issue 2 https://doi.org/10.1039/B712872J	journal	January 2008
C−H Bond Cleavage with Reductants: Re-Investigating the Reactivity of Monomeric Mn ^III/IV −Oxo Complexes and the Role of Oxo Ligand Basicity Parsell, Trenton H.; Yang, Meng-Yin; Borovik, A. S. Journal of the American Chemical Society, Vol. 131, Issue 8 https://doi.org/10.1021/ja8100825	journal	March 2009
Monomeric Mn III/II and Fe III/II Complexes with Terminal Hydroxo and Oxo Ligands: Probing Reactivity via O−H Bond Dissociation Energies Gupta, Rajeev; Borovik, A. S. Journal of the American Chemical Society, Vol. 125, Issue 43 https://doi.org/10.1021/ja030149l	journal	October 2003
Probing the Compound I-like Reactivity of a Bare High-Valent Oxo Iron Porphyrin Complex: The Oxidation of Tertiary Amines Chiavarino, Barbara; Cipollini, Romano; Crestoni, Maria Elisa Journal of the American Chemical Society, Vol. 130, Issue 10 https://doi.org/10.1021/ja077286t	journal	March 2008
Density Functional Theory Study of Hydrogen Atom Abstraction from a Series of para -Substituted Phenols: Why is the Hammett σ p + Constant Able to Represent Radical Reaction Rates? Yoshida, Tatsusada; Hirozumi, Koji; Harada, Masataka The Journal of Organic Chemistry, Vol. 76, Issue 11 https://doi.org/10.1021/jo200450p	journal	June 2011
Bond Strengths of Toluenes, Anilines, and Phenols: To Hammett or Not Pratt, Derek A.; DiLabio, Gino A.; Mulder, Peter Accounts of Chemical Research, Vol. 37, Issue 5 https://doi.org/10.1021/ar010010k	journal	May 2004
Reactivity of the copper( iii )-hydroxide unit with phenols Dhar, Debanjan; Yee, Gereon M.; Markle, Todd F. Chemical Science, Vol. 8, Issue 2 https://doi.org/10.1039/C6SC03039D	journal	January 2017
Hydrogen Atom Abstraction by a High-Valent Manganese(V)−Oxo Corrolazine Lansky, David E.; Goldberg, David P. Inorganic Chemistry, Vol. 45, Issue 13 https://doi.org/10.1021/ic060491+	journal	May 2006
Oxygen-hydrogen bond dissociation energies in para-substituted phenols Mulder, P.; Saastad, O. W.; Griller, D. Journal of the American Chemical Society, Vol. 110, Issue 12 https://doi.org/10.1021/ja00220a088	journal	June 1988
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
Oxidation of C−H Bonds by [(bpy) 2 (py)Ru IV O] 2+ Occurs by Hydrogen Atom Abstraction Bryant, Jasmine R.; Mayer, James M. Journal of the American Chemical Society, Vol. 125, Issue 34 https://doi.org/10.1021/ja035276w	journal	August 2003
A Continuum of Proton-Coupled Electron Transfer Reactivity Darcy, Julia W.; Koronkiewicz, Brian; Parada, Giovanny A. Accounts of Chemical Research, Vol. 51, Issue 10 https://doi.org/10.1021/acs.accounts.8b00319	journal	September 2018
pKa values in organic chemistry – Making maximum use of the available data Kütt, Agnes; Selberg, Sigrid; Kaljurand, Ivari Tetrahedron Letters, Vol. 59, Issue 42 https://doi.org/10.1016/j.tetlet.2018.08.054	journal	October 2018
Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications Warren, Jeffrey J.; Tronic, Tristan A.; Mayer, James M. Chemical Reviews, Vol. 110, Issue 12 https://doi.org/10.1021/cr100085k	journal	December 2010
A general treatment of hydrogen bond complexation constants in tetrachloromethane Abraham, Michael H.; Grellier, Priscilla L.; Prior, David V. Journal of the American Chemical Society, Vol. 110, Issue 25 https://doi.org/10.1021/ja00233a034	journal	December 1988
Predicting organic hydrogen atom transfer rate constants using the Marcus cross relation Warren, J. J.; Mayer, J. M. Proceedings of the National Academy of Sciences, Vol. 107, Issue 12 https://doi.org/10.1073/pnas.0910347107	journal	March 2010
Enthalpy of Formation of the Cyclohexadienyl Radical and the C−H Bond Enthalpy of 1,4-Cyclohexadiene: An Experimental and Computational Re-Evaluation Gao, Yide; DeYonker, Nathan J.; Garrett, E. Chauncey The Journal of Physical Chemistry A, Vol. 113, Issue 25 https://doi.org/10.1021/jp901314y	journal	June 2009
Quantum Chemical Modeling of the Oxidation of Dihydroanthracene by the Biomimetic Nonheme Iron Catalyst [(TMC)Fe IV (O)] 2+ Johansson, Adam Johannes; Blomberg, Margareta R. A.; Siegbahn, Per E. M. The Journal of Physical Chemistry C, Vol. 111, Issue 33 https://doi.org/10.1021/jp0730444	journal	August 2007
Chemistry of the t -Butoxyl Radical: Evidence that Most Hydrogen Abstractions from Carbon are Entropy-Controlled Finn, Meghan; Friedline, Robert; Suleman, N. Kamrudin Journal of the American Chemical Society, Vol. 126, Issue 24 https://doi.org/10.1021/ja0493493	journal	June 2004
Mechanism of phenol oxidation by heterodinuclear Ni Cu bis(μ-oxo) complexes involving nucleophilic oxo groups Kundu, Subrata; Miceli, Enrico; Farquhar, Erik R. Dalton Trans., Vol. 43, Issue 11 https://doi.org/10.1039/C3DT52644E	journal	January 2014
C−H Bond Activation by a Ferric Methoxide Complex: Modeling the Rate-Determining Step in the Mechanism of Lipoxygenase Goldsmith, Christian R.; Jonas, Robert T.; Stack, T. Daniel P. Journal of the American Chemical Society, Vol. 124, Issue 1 https://doi.org/10.1021/ja016451g	journal	January 2002
Properties of the oxo/aqua system (bpy)2(py)RuO2+/(bpy)2(py)Ru(OH2)2+ Moyer, Bruce A.; Meyer, Thomas J. Inorganic Chemistry, Vol. 20, Issue 2 https://doi.org/10.1021/ic50216a024	journal	February 1981
Mechanistic Implications of Proton Transfer Coupled to Electron Transfer Lebeau, Estelle L.; Binstead, Robert A.; Meyer, Thomas J. Journal of the American Chemical Society, Vol. 123, Issue 43 https://doi.org/10.1021/ja000517a	journal	October 2001
Electrocatalytic water oxidation by a molecular cobalt complex through a high valent cobalt oxo intermediate Das, Debasree; Pattanayak, Santanu; Singh, Kundan K. Chemical Communications, Vol. 52, Issue 79 https://doi.org/10.1039/C6CC05773J	journal	January 2016
Homogeneous Electrocatalytic Water Oxidation at Neutral pH by a Robust Macrocyclic Nickel(II) Complex Zhang, Mei; Zhang, Ming-Tian; Hou, Cheng Angewandte Chemie International Edition, Vol. 53, Issue 48 https://doi.org/10.1002/anie.201406983	journal	September 2014
Bond Strengths of Toluenes, Anilines, and Phenols: To Hammett or Not Pratt, Derek A.; Dilabio, Gino A.; Mulder, Peter ChemInform, Vol. 35, Issue 30 https://doi.org/10.1002/chin.200430297	journal	July 2004
Proton-Coupled Electron Transfer J., Meyer, Thomas; V., Huynh, My Hang The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/cywa-5d70	text	January 2007
Use of a Metallopeptide-Based Mimic Provides Evidence for a Proton-Coupled Electron-Transfer Mechanism for Superoxide Reduction by Nickel-Containing Superoxide Dismutase Shearer, Jason Angewandte Chemie, Vol. 125, Issue 9 https://doi.org/10.1002/ange.201209746	journal	January 2013
Homogeneous Electrocatalytic Water Oxidation at Neutral pH by a Robust Macrocyclic Nickel(II) Complex Zhang, Mei; Zhang, Ming-Tian; Hou, Cheng Angewandte Chemie, Vol. 126, Issue 48 https://doi.org/10.1002/ange.201406983	journal	September 2014
Proton-Coupled Electron Transfer Cukier, Robert I.; Nocera, Daniel G. Annual Review of Physical Chemistry, Vol. 49, Issue 1 https://doi.org/10.1146/annurev.physchem.49.1.337	journal	October 1998
Characterization and Reactivity of a Terminal Nickel(III)-Oxygen Adduct Pirovano, Paolo; Farquhar, Erik R.; Swart, Marcel Chemistry - A European Journal, Vol. 21, Issue 9 https://doi.org/10.1002/chem.201406485	journal	January 2015
Bond Strengths of Toluenes, Anilines, and Phenols: To Hammett or Not Pratt, Derek A.; Dilabio, Gino A.; Mulder, Peter ChemInform, Vol. 35, Issue 30 https://doi.org/10.1002/chin.200430297	journal	July 2004
A Pyridine Alkoxide Chelate Ligand That Promotes Both Unusually High Oxidation States and Water-Oxidation Catalysis Michaelos, Thoe K.; Shopov, Dimitar Y.; Sinha, Shashi Bhushan Accounts of Chemical Research, Vol. 50, Issue 4 https://doi.org/10.1021/acs.accounts.6b00652	journal	February 2017
A Continuum of Proton-Coupled Electron Transfer Reactivity Darcy, Julia W.; Koronkiewicz, Brian; Parada, Giovanny A. Accounts of Chemical Research, Vol. 51, Issue 10 https://doi.org/10.1021/acs.accounts.8b00319	journal	September 2018
A Dinuclear Iridium(V,V) Oxo-Bridged Complex Characterized Using a Bulk Electrolysis Technique for Crystallizing Highly Oxidizing Compounds Shopov, Dimitar Y.; Sharninghausen, Liam S.; Sinha, Shashi Bhushan Inorganic Chemistry, Vol. 57, Issue 9 https://doi.org/10.1021/acs.inorgchem.8b00757	journal	April 2018
Insight into the Structure and Mechanism of Nickel-Containing Superoxide Dismutase Derived from Peptide-Based Mimics Shearer, Jason Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500060s	journal	May 2014
Nickel Superoxide Dismutase Structure and Mechanism ^† Barondeau, David P.; Kassmann, Carey J.; Bruns, Cami K. Biochemistry, Vol. 43, Issue 25 https://doi.org/10.1021/bi0496081	journal	June 2004
Mechanism of Oxidation Reactions Catalyzed by Cytochrome P450 Enzymes Meunier, Bernard; de Visser, Samuël P.; Shaik, Sason Chemical Reviews, Vol. 104, Issue 9 https://doi.org/10.1021/cr020443g	journal	September 2004
Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications Warren, Jeffrey J.; Tronic, Tristan A.; Mayer, James M. Chemical Reviews, Vol. 110, Issue 12 https://doi.org/10.1021/cr100085k	journal	December 2010
Mechanistic Implications of Proton Transfer Coupled to Electron Transfer Lebeau, Estelle L.; Binstead, Robert A.; Meyer, Thomas J. Journal of the American Chemical Society, Vol. 123, Issue 43 https://doi.org/10.1021/ja000517a	journal	October 2001
Monomeric Mn III/II and Fe III/II Complexes with Terminal Hydroxo and Oxo Ligands: Probing Reactivity via O−H Bond Dissociation Energies Gupta, Rajeev; Borovik, A. S. Journal of the American Chemical Society, Vol. 125, Issue 43 https://doi.org/10.1021/ja030149l	journal	October 2003
Oxidation of C−H Bonds by [(bpy) 2 (py)Ru IV O] 2+ Occurs by Hydrogen Atom Abstraction Bryant, Jasmine R.; Mayer, James M. Journal of the American Chemical Society, Vol. 125, Issue 34 https://doi.org/10.1021/ja035276w	journal	August 2003
Chemistry of the t -Butoxyl Radical: Evidence that Most Hydrogen Abstractions from Carbon are Entropy-Controlled Finn, Meghan; Friedline, Robert; Suleman, N. Kamrudin Journal of the American Chemical Society, Vol. 126, Issue 24 https://doi.org/10.1021/ja0493493	journal	June 2004
Probing the Compound I-like Reactivity of a Bare High-Valent Oxo Iron Porphyrin Complex: The Oxidation of Tertiary Amines Chiavarino, Barbara; Cipollini, Romano; Crestoni, Maria Elisa Journal of the American Chemical Society, Vol. 130, Issue 10 https://doi.org/10.1021/ja077286t	journal	March 2008
C−H Bond Cleavage with Reductants: Re-Investigating the Reactivity of Monomeric Mn ^III/IV −Oxo Complexes and the Role of Oxo Ligand Basicity Parsell, Trenton H.; Yang, Meng-Yin; Borovik, A. S. Journal of the American Chemical Society, Vol. 131, Issue 8 https://doi.org/10.1021/ja8100825	journal	March 2009
Pivotal Role and Regulation of Proton Transfer in Water Oxidation on Hematite Photoanodes Zhang, Yuchao; Zhang, Hongna; Ji, Hongwei Journal of the American Chemical Society, Vol. 138, Issue 8 https://doi.org/10.1021/jacs.5b12069	journal	February 2016
High Oxidation State Iridium Mono-μ-oxo Dimers Related to Water Oxidation Catalysis Sharninghausen, Liam S.; Sinha, Shashi Bhushan; Shopov, Dimitar Y. Journal of the American Chemical Society, Vol. 138, Issue 49 https://doi.org/10.1021/jacs.6b07716	journal	December 2016
Tuning the Reactivity of Terminal Nickel(III)–Oxygen Adducts for C–H Bond Activation Pirovano, Paolo; Farquhar, Erik R.; Swart, Marcel Journal of the American Chemical Society, Vol. 138, Issue 43 https://doi.org/10.1021/jacs.6b08406	journal	October 2016
Redox Activity of Oxo-Bridged Iridium Dimers in an N,O-Donor Environment: Characterization of Remarkably Stable Ir(IV,V) Complexes Sinha, Shashi Bhushan; Shopov, Dimitar Y.; Sharninghausen, Liam S. Journal of the American Chemical Society, Vol. 139, Issue 28 https://doi.org/10.1021/jacs.7b04874	journal	July 2017
Hydrogen Atom Transfer by a High-Valent Nickel-Chloride Complex Mondal, Prasenjit; Pirovano, Paolo; Das, Ankita Journal of the American Chemical Society, Vol. 140, Issue 5 https://doi.org/10.1021/jacs.7b11953	journal	January 2018
Enthalpy of Formation of the Cyclohexadienyl Radical and the C−H Bond Enthalpy of 1,4-Cyclohexadiene: An Experimental and Computational Re-Evaluation Gao, Yide; DeYonker, Nathan J.; Garrett, E. Chauncey The Journal of Physical Chemistry A, Vol. 113, Issue 25 https://doi.org/10.1021/jp901314y	journal	June 2009
Oxidizing species in the mechanism of cytochrome P450 Ortiz de Montellano, Paul R.; De Voss, James J. Natural Product Reports, Vol. 19, Issue 4 https://doi.org/10.1039/b101297p	journal	May 2002
Radical reactivity of the Fe( iii )/( ii ) tetramesitylporphyrin couple: hydrogen atom transfer, oxyl radical dissociation, and catalytic disproportionation of a hydroxylamine Porter, Thomas R.; Mayer, James M. Chem. Sci., Vol. 5, Issue 1 https://doi.org/10.1039/c3sc52055b	journal	January 2014
Predicting organic hydrogen atom transfer rate constants using the Marcus cross relation Warren, J. J.; Mayer, J. M. Proceedings of the National Academy of Sciences, Vol. 107, Issue 12 https://doi.org/10.1073/pnas.0910347107	journal	March 2010

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CCDC 1954011: Experimental Crystal Structure Determination J., Fisher, Katherine; L., Feuer, Margalit; C., Lant, Hannah M. https://doi.org/10.5517/ccdc.csd.cc23l9mn The current record is supplemented by this dataset	dataset	January 2020
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