High-Potential Electrocatalytic O2 Reduction with Nitroxyl / NOx Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis

Gerken, James B.; Stahl, Shannon S.

doi:10.1021/acscentsci.5b00163

Title: High-Potential Electrocatalytic O2 Reduction with Nitroxyl / NOx Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis

Journal Article · Wed Jul 15 00:00:00 EDT 2015 · ACS Central Science (Online)

DOI:https://doi.org/10.1021/acscentsci.5b00163· OSTI ID:1229947

Gerken, James B.; Stahl, Shannon S.

Efficient reduction of O2 to water is a central challenge in energy conversion and aerobic oxidation catalysis. In the present study, we investigate the electrochemical reduction of O2 with soluble organic nitroxyl and nitrogen oxide (NOx) mediators. When used alone, neither organic nitroxyls, such as TEMPO (2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl), nor NOx species, such as sodium nitrite, are effective mediators of electrochemical O2 reduction. The combination of nitroxyl/NOx species, however, mediates sustained O2 reduction at electrochemical potentials of 0.19–0.33 V (vs. Fc/Fc+) in acetonitrile containing trifluoroacetic acid. Mechanistic analysis of the coupled redox reactions supports a process in which the nitrogen oxide catalyst drives aerobic oxidation of a nitroxyl mediator to an oxoammonium species, which then is reduced back to the nitroxyl at the cathode. The electrolysis potential is dictated by the oxoammonium/nitroxyl reduction potential. The high potentials observed with this ORR system benefit from the mechanism-based specificity for four-electron reduction of oxygen to water mediated by NOx species, together with kinetically efficient reduction of oxidized NOx species by TEMPO and other organic nitroxyls. This research was supported as part of the Center for Molecular Electrocatalysis, an Energy Frontier Research Center, funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences.

Cite

Export

Save

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Molecular Electrocatalysis (CME); Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1229947

Report Number(s):: PNNL-SA-106633; KC0307010

Journal Information:: ACS Central Science (Online), Vol. 1, Issue 5; ISSN 2374-7951

Country of Publication:: United States

Language:: English

References (94)

Efficient Aerobic Oxidation of Secondary Alcohols at Ambient Temperature with an ABNO/NO _x Catalyst System Lauber, Markus B.; Stahl, Shannon S. ACS Catalysis, Vol. 3, Issue 11 https://doi.org/10.1021/cs400746m	journal	October 2013
Aerobic oxidation catalysis with stable radicals Cao, Qun; Dornan, Laura M.; Rogan, Luke Chem. Commun., Vol. 50, Issue 35 https://doi.org/10.1039/C3CC47081D	journal	January 2014
Potent catalysis of the electroreduction of oxygen to water by dicobalt porphyrin dimers adsorbed on graphite electrodes Collman, James P.; Marrocco, Matt; Denisevich, Peter Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 101, Issue 1 https://doi.org/10.1016/S0022-0728(79)80085-6	journal	July 1979
Multicopper Models for the Laccase Active Site: Effect of Nuclearity on Electrocatalytic Oxygen Reduction Tse, Edmund C. M.; Schilter, David; Gray, Danielle L. Inorganic Chemistry, Vol. 53, Issue 16 https://doi.org/10.1021/ic501080c	journal	July 2014
From Structural Models of Galactose Oxidase to Homogeneous Catalysis: Efficient Aerobic Oxidation of Alcohols Chaudhuri, Phalguni; Hess, Martina; Flörke, Ulrich Angewandte Chemie International Edition, Vol. 37, Issue 16 https://doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D	journal	September 1998
Electrode catalysis of the four-electron reduction of oxygen to water by dicobalt face-to-face porphyrins Collman, James P.; Denisevich, Peter; Konai, Yutaka Journal of the American Chemical Society, Vol. 102, Issue 19 https://doi.org/10.1021/ja00539a009	journal	September 1980
Role of Proton-Coupled Electron Transfer in O–O Bond Activation Rosenthal, Joel; Nocera, Daniel G. Accounts of Chemical Research, Vol. 40, Issue 7 https://doi.org/10.1021/ar7000638	journal	July 2007
Aerobic Alcohol Oxidations Mediated by Nitric Acid Aellig, Christof; Girard, Christophe; Hermans, Ive Angewandte Chemie International Edition, Vol. 50, Issue 51 https://doi.org/10.1002/anie.201105620	journal	October 2011
Electrocatalytic O ₂ Reduction by Covalently Immobilized Mononuclear Copper(I) Complexes: Evidence for a Binuclear Cu ₂ O ₂ Intermediate McCrory, Charles C. L.; Devadoss, Anando; Ottenwaelder, Xavier Journal of the American Chemical Society, Vol. 133, Issue 11 https://doi.org/10.1021/ja106338h	journal	March 2011
Analysis of Porphyrines as Catalysts for Electrochemical Reduction of O ₂ and Oxidation of H ₂ O Baran, Jakub D.; Grönbeck, Henrik; Hellman, Anders Journal of the American Chemical Society, Vol. 136, Issue 4 https://doi.org/10.1021/ja4060299	journal	January 2014
Kinetic studies on the single electron transfer reaction between 2, 2, 6, 6-tetramethylpiperidine oxoammonium ions and phenothiazines: the application of Marcus theory Wu, Longmin; Guo, Xia; Wang, Jun Science in China Series B: Chemistry, Vol. 42, Issue 2 https://doi.org/10.1007/BF02875509	journal	April 1999
Redox catalysis in organic electrosynthesis: basic principles and recent developments Francke, Robert; Little, R. Daniel Chemical Society Reviews, Vol. 43, Issue 8 https://doi.org/10.1039/c3cs60464k	journal	January 2014
High-Oxidation-State Palladium Catalysis: New Reactivity for Organic Synthesis Muñiz, Kilian Angewandte Chemie International Edition, Vol. 48, Issue 50 https://doi.org/10.1002/anie.200903671	journal	October 2009
Accurate Rate Constants for Decomposition of Aqueous Nitrous Acid Rayson, Mark S.; Mackie, John C.; Kennedy, Eric M. Inorganic Chemistry, Vol. 51, Issue 4 https://doi.org/10.1021/ic202081z	journal	January 2012
Catalytic Oxidation of Organic Substrates by Molecular Oxygen and Hydrogen Peroxide by Multistep Electron Transfer—A Biomimetic Approach Piera, Julio; Bäckvall, Jan-E. Angewandte Chemie International Edition, Vol. 47, Issue 19 https://doi.org/10.1002/anie.200700604	journal	April 2008
Kinetics and mechanism of the comproportionation reaction between oxoammonium cation and hydroxylamine derived from cyclic nitroxides Israeli, Avner; Patt, Miriam; Oron, Miriam Free Radical Biology and Medicine, Vol. 38, Issue 3 https://doi.org/10.1016/j.freeradbiomed.2004.09.037	journal	February 2005
Direct Determination of Equilibrium Potentials for Hydrogen Oxidation/Production by Open Circuit Potential Measurements in Acetonitrile Roberts, John A. S.; Bullock, R. Morris Inorganic Chemistry, Vol. 52, Issue 7 https://doi.org/10.1021/ic302461q	journal	June 2012
Mechanistic Study of Alcohol Oxidation by the Pd(OAc) ₂ /O ₂ /DMSO Catalyst System and Implications for the Development of Improved Aerobic Oxidation Catalysts Steinhoff, Bradley A.; Fix, Shannon R.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 124, Issue 5 https://doi.org/10.1021/ja016806w	journal	February 2002
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-Butyl Nitrite/Oxygen: A Versatile Catalytic Oxidation System Shen, Zhenlu; Dai, Jialiang; Xiong, Jie Advanced Synthesis & Catalysis, Vol. 353, Issue 16 https://doi.org/10.1002/adsc.201100429	journal	November 2011
Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin Rahimi, Alireza; Azarpira, Ali; Kim, Hoon Journal of the American Chemical Society, Vol. 135, Issue 17, p. 6415-6418 https://doi.org/10.1021/ja401793n	journal	April 2013
Reduction Potentials of One‐Electron Couples Involving Free Radicals in Aqueous Solution Wardman, Peter Journal of Physical and Chemical Reference Data, Vol. 18, Issue 4 https://doi.org/10.1063/1.555843	journal	October 1989
Aerobic oxidative deprotection of benzyl-type ethers under atmospheric pressure catalyzed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/tert-butyl nitrite Shen, Zhenlu; Sheng, Lili; Zhang, Xiaochu Tetrahedron Letters, Vol. 54, Issue 12 https://doi.org/10.1016/j.tetlet.2013.01.045	journal	March 2013
Palladium-catalyzed aerobic acetoxylation of benzene using NOx-based redox mediators Zultanski, Susan L.; Stahl, Shannon S. Journal of Organometallic Chemistry, Vol. 793 https://doi.org/10.1016/j.jorganchem.2015.03.003	journal	September 2015
Combined Redox Couples for Catalytic Oxidation of Methane by Dioxygen at Low Temperatures An, Zengjian; Pan, Xiulian; Liu, Xiumei Journal of the American Chemical Society, Vol. 128, Issue 50 https://doi.org/10.1021/ja0647912	journal	December 2006
Cobalt(III) Corroles as Electrocatalysts for the Reduction of Dioxygen: Reactivity of a Monocorrole, Biscorroles, and Porphyrin−Corrole Dyads Kadish, Karl M.; Frémond, Laurent; Ou, Zhongping Journal of the American Chemical Society, Vol. 127, Issue 15 https://doi.org/10.1021/ja0501060	journal	April 2005
Efficient reduction of dioxygen with ferrocene derivatives, catalyzed by metalloporphyrins in the presence of perchloric acid Fukuzumi, Shunichi; Mochizuki, Seiji; Tanaka, Toshio Inorganic Chemistry, Vol. 28, Issue 12 https://doi.org/10.1021/ic00311a042	journal	June 1989
Dioxygen activation by an organometallic Pd( ii ) precursor: formation of a Pd( iv )–OH complex and its C–O bond formation reactivity Qu, Fengrui; Khusnutdinova, Julia R.; Rath, Nigam P. Chem. Commun., Vol. 50, Issue 23 https://doi.org/10.1039/C3CC49387C	journal	January 2014
The Aerobic Oxidation of a Pd(II) Dimethyl Complex Leads to Selective Ethane Elimination from a Pd(III) Intermediate Khusnutdinova, Julia R.; Rath, Nigam P.; Mirica, Liviu M. Journal of the American Chemical Society, Vol. 134, Issue 4 https://doi.org/10.1021/ja210841f	journal	January 2012
Biochemistry of nitric oxide and its redox-activated forms Stamler, J.; Singel, D.; Loscalzo, J. Science, Vol. 258, Issue 5090 https://doi.org/10.1126/science.1281928	journal	December 1992
Oxygen Electrochemistry as a Cornerstone for Sustainable Energy Conversion Katsounaros, Ioannis; Cherevko, Serhiy; Zeradjanin, Aleksandar R. Angewandte Chemie International Edition, Vol. 53, Issue 1 https://doi.org/10.1002/anie.201306588	journal	December 2013
Bimetallic Redox Synergy in Oxidative Palladium Catalysis Powers, David C.; Ritter, Tobias Accounts of Chemical Research, Vol. 45, Issue 6 https://doi.org/10.1021/ar2001974	journal	October 2011
Selective Oxidation of Unsaturated Alcohols Catalyzed by Sodium Nitrite and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone with Molecular Oxygen under Mild Conditions Wang, Lianyue; Li, Jun; Yang, Hua The Journal of Organic Chemistry, Vol. 77, Issue 1 https://doi.org/10.1021/jo202301s	journal	December 2011
Electrocatalytic Oxygen Reduction by Iron Tetra-arylporphyrins Bearing Pendant Proton Relays Carver, Colin T.; Matson, Benjamin D.; Mayer, James M. Journal of the American Chemical Society, Vol. 134, Issue 12 https://doi.org/10.1021/ja211987f	journal	March 2012
Electrocatalysis of oxygen reduction. 5. Oxygen to hydrogen peroxide conversion by cobalt(II) tetrakis(N-methyl-4-pyridyl)porphyrin Chan, Ray J. H.; Su, Y. Oliver; Kuwana, Theodore Inorganic Chemistry, Vol. 24, Issue 23 https://doi.org/10.1021/ic00217a017	journal	November 1985
On the Theory of Electron‐Transfer Reactions. VI. Unified Treatment for Homogeneous and Electrode Reactions Marcus, R. A. The Journal of Chemical Physics, Vol. 43, Issue 2 https://doi.org/10.1063/1.1696792	journal	July 1965
Novel Multinuclear Catalysts for the Electroreduction of Dioxygen Directly to Water Anson, Fred C.; Shi, Chunnian; Steiger, Beat Accounts of Chemical Research, Vol. 30, Issue 11 https://doi.org/10.1021/ar960264j	journal	November 1997
Functional Analogues of Cytochrome c Oxidase, Myoglobin, and Hemoglobin Collman, James P.; Boulatov, Roman; Sunderland, Christopher J. Chemical Reviews, Vol. 104, Issue 2 https://doi.org/10.1021/cr0206059	journal	February 2004
Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions Lyons, Thomas W.; Sanford, Melanie S. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900184e	journal	February 2010
Hangman Corroles: Efficient Synthesis and Oxygen Reaction Chemistry Dogutan, Dilek K.; Stoian, Sebastian A.; McGuire, Robert Journal of the American Chemical Society, Vol. 133, Issue 1 https://doi.org/10.1021/ja108904s	journal	January 2011
Electrocatalytic reduction of molecular oxygen using non-planar cobalt tetrakis-(4-sulfonatophenyl)-β-octabromoporphyrin D'Souza, Francis; Hsieh, Yi-Ying; Deviprasad, G. R. Journal of Electroanalytical Chemistry, Vol. 426, Issue 1-2 https://doi.org/10.1016/S0022-0728(97)00040-5	journal	April 1997
Efficient Two-Electron Reduction of Dioxygen to Hydrogen Peroxide with One-Electron Reductants with a Small Overpotential Catalyzed by a Cobalt Chlorin Complex Mase, Kentaro; Ohkubo, Kei; Fukuzumi, Shunichi Journal of the American Chemical Society, Vol. 135, Issue 7 https://doi.org/10.1021/ja312199h	journal	February 2013
Molecular Catalysis of Electrochemical Reactions. Mechanistic Aspects Savéant, Jean-Michel Chemical Reviews, Vol. 108, Issue 7, p. 2348-2378 https://doi.org/10.1021/cr068079z	journal	July 2008
Homogeneous catalysis of the electrochemical reduction of dioxygen by a macrocyclic cobalt(III) complex Geiger, Thomas; Anson, Fred C. Journal of the American Chemical Society, Vol. 103, Issue 25 https://doi.org/10.1021/ja00415a016	journal	December 1981
Dinitrogen trioxide. Part XI. The electronic spectrum of dinitrogen trioxide Shaw, A. W.; Vosper, A. J. Journal of the Chemical Society, Dalton Transactions, Issue 8-9 https://doi.org/10.1039/dt9720000961	journal	January 1972
Mechanistic Insight into Aerobic Alcohol Oxidation Using NO _x –Nitroxide Catalysis Based on Catalyst Structure–Activity Relationships Shibuya, Masatoshi; Nagasawa, Shota; Osada, Yuji The Journal of Organic Chemistry, Vol. 79, Issue 21 https://doi.org/10.1021/jo501862k	journal	October 2014
Nitrate as a redox co-catalyst for the aerobic Pd-catalyzed oxidation of unactivated sp3-C–H bonds Stowers, Kara J.; Kubota, Asako; Sanford, Melanie S. Chemical Science, Vol. 3, Issue 11 https://doi.org/10.1039/c2sc20800h	journal	January 2012
The NO2 absorption spectrum. II. Absorption cross-sections at low temperatures in the 400?500 nm region Coquart, B.; Jenouvrier, A.; Merienne, M. F. Journal of Atmospheric Chemistry, Vol. 21, Issue 3 https://doi.org/10.1007/BF00696757	journal	July 1995
The use of cyclic nitroxide radicals as HNO scavengers Samuni, Yuval; Samuni, Uri; Goldstein, Sara Journal of Inorganic Biochemistry, Vol. 118 https://doi.org/10.1016/j.jinorgbio.2012.10.002	journal	January 2013
H ₂ Evolution and Molecular Electrocatalysts: Determination of Overpotentials and Effect of Homoconjugation Fourmond, Vincent; Jacques, Pierre-André; Fontecave, Marc Inorganic Chemistry, Vol. 49, Issue 22 https://doi.org/10.1021/ic101187v	journal	November 2010
Reaction of Cyclic Nitroxides with Nitrogen Dioxide: The Intermediacy of the Oxoammonium Cations Goldstein, Sara; Samuni, Amram; Russo, Angelo Journal of the American Chemical Society, Vol. 125, Issue 27 https://doi.org/10.1021/ja035286x	journal	July 2003
Nitroxide-catalyzed transition-metal-free aerobic oxidation processes Wertz, Sebastian; Studer, Armido Green Chemistry, Vol. 15, Issue 11 https://doi.org/10.1039/c3gc41459k	journal	January 2013
Solvent dynamical effects on the electron self-exchange rate of the TEMPO˙/TEMPO + couple (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy radical) : Part I. ESR-linebroadening measurements at T = 298 K Grampp, Guenter; Rasmussen, Kenneth Phys. Chem. Chem. Phys., Vol. 4, Issue 22 https://doi.org/10.1039/B206313A	journal	January 2002
Transition-Metal-Free: A Highly Efficient Catalytic Aerobic Alcohol Oxidation Process Liu, Renhua; Liang, Xinmiao; Dong, Chunyan Journal of the American Chemical Society, Vol. 126, Issue 13 https://doi.org/10.1021/ja031765k	journal	April 2004
Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation Hoover, Jessica M.; Ryland, Bradford L.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 135, Issue 6 https://doi.org/10.1021/ja3117203	journal	January 2013
A Redox Fuel Cell That Operates with Methane as Fuel at 120 C Bergens, S. H.; Gorman, C. B.; Palmore, G. T. R. Science, Vol. 265, Issue 5177 https://doi.org/10.1126/science.265.5177.1418	journal	September 1994
The oxidative coupling of benzylic compounds catalyzed by 2,3-dichloro-5,6-dicyano-benzoquinone and sodium nitrite using molecular oxygen as a co-oxidant Cheng, Dongping; Yuan, Kun; Xu, Xiaoliang Tetrahedron Letters, Vol. 56, Issue 13 https://doi.org/10.1016/j.tetlet.2015.02.018	journal	March 2015
Determination of Rate Constants in Second-Order Kinetics Using UV-Visible Spectroscopy Bijlsma, Sabina; Boelens, Hans F. M.; Smilde, Age K. Applied Spectroscopy, Vol. 55, Issue 1 https://doi.org/10.1366/0003702011951281	journal	January 2001
Spectroscopic and Optimization Modeling Study of Nitrous Acid in Aqueous Solution Riordan, Eoin; Minogue, Nicholas; Healy, David The Journal of Physical Chemistry A, Vol. 109, Issue 5 https://doi.org/10.1021/jp040269v	journal	February 2005
Mechanistic - Kinetic Scheme of Oxidation/Reduction of TEMPO Involving Hydrogen Bonded Dimer. RDE Probe for Availability of Protons in Reaction Environment Janiszewska, Anna?Maria; Grzeszczuk, Maria Electroanalysis, Vol. 16, Issue 20 https://doi.org/10.1002/elan.200303011	journal	October 2004
Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin Lancefield, Christopher S.; Ojo, O. Stephen; Tran, Fanny Angewandte Chemie International Edition, Vol. 54, Issue 1 https://doi.org/10.1002/anie.201409408	journal	November 2014
Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant Gligorich, Keith M.; Sigman, Matthew S. Chemical Communications, Issue 26 https://doi.org/10.1039/b902868d	journal	January 2009
Electronic effects in transition metal porphyrins. 2. The sensitivity of redox and ligand addition reactions in para-substituted tetraphenylporphyrin complexes of cobalt(II) Walker, F. Ann; Beroiz, D.; Kadish, K. M. Journal of the American Chemical Society, Vol. 98, Issue 12 https://doi.org/10.1021/ja00428a016	journal	June 1976
Activity benchmarks and requirements for Pt, Pt-alloy, and non-Pt oxygen reduction catalysts for PEMFCs Gasteiger, Hubert A.; Kocha, Shyam S.; Sompalli, Bhaskar Applied Catalysis B: Environmental, Vol. 56, Issue 1-2, p. 9-35 https://doi.org/10.1016/j.apcatb.2004.06.021	journal	March 2005
A mechanistic glimpse into the oxidation of alcohols using TEMPO/NOx catalytic systems: towards a greener bifunctional catalyst Ionita, Petre RSC Advances, Vol. 3, Issue 44 https://doi.org/10.1039/c3ra44863k	journal	January 2013
Catalytic Activity of Biscobalt Porphyrin-Corrole Dyads Toward the Reduction of Dioxygen Kadish, Karl M.; Frémond, Laurent; Shen, Jing Inorganic Chemistry, Vol. 48, Issue 6 https://doi.org/10.1021/ic802092n	journal	March 2009
Aerobic Oxidation of Pd ^II to Pd ^IV by Active Radical Reactants: Direct C–H Nitration and Acylation of Arenes via Oxygenation Process with Molecular Oxygen Liang, Yu-Feng; Li, Xinyao; Wang, Xiaoyang ACS Catalysis, Vol. 5, Issue 3 https://doi.org/10.1021/cs502126n	journal	February 2015
Anaerobic Nitroxide-Catalyzed Oxidation of Alcohols Using the NO ⁺ /NO· Redox Pair Holan, Martin; Jahn, Ullrich Organic Letters, Vol. 16, Issue 1 https://doi.org/10.1021/ol403016p	journal	December 2013
Oxygen carrier and redox properties of some neutral cobalt chelates. Axial and in-plane ligand effects Carter, Mark J.; Rillema, D. Paul; Basolo, Fred Journal of the American Chemical Society, Vol. 96, Issue 2, p. 392-400 https://doi.org/10.1021/ja00809a012	journal	January 1974
Exploration of gas sensing possibilities with edge plane pyrolytic graphite electrodes: nitrogen dioxide detection Banks, Craig E.; Goodwin, Alexander; Heald, Charles G. R. The Analyst, Vol. 130, Issue 3 https://doi.org/10.1039/b416715e	journal	January 2005
Nitrogen Cycle Electrocatalysis Rosca, Victor; Duca, Matteo; de Groot, Matheus T. Chemical Reviews, Vol. 109, Issue 6 https://doi.org/10.1021/cr8003696	journal	June 2009
Organic Nitrosonium Salts. II. Stability Studies and Oxidations of Some Indole Derivatives M. Bobbitt, James; M. Bobbitt, James; Cecile Flores Guttermuth, M. HETEROCYCLES, Vol. 30, Issue 2 https://doi.org/10.3987/COM-89-S112	journal	January 1990
Recommendations on reporting electrode potentials in nonaqueous solvents (Provisional) Gritzner, G.; Kuta, J. Pure and Applied Chemistry, Vol. 54, Issue 8 https://doi.org/10.1351/pac198254081527	journal	January 1982
Mechanistic aspects of the catalytic reduction of dioxygen by cofacial metalloporphyrins Durand, Richard R.; Bencosme, C. Susana; Collman, James P. Journal of the American Chemical Society, Vol. 105, Issue 9 https://doi.org/10.1021/ja00347a032	journal	May 1983
Molecular Oxygen To Regenerate PdII Active Species Muzart, Jacques Chemistry – An Asian Journal, Vol. 1, Issue 4 https://doi.org/10.1002/asia.200600202	journal	October 2006
Highly Efficient Catalytic Aerobic Oxidations of Benzylic Alcohols in Water Liu, Renhua; Dong, Chunyan; Liang, Xinmiao The Journal of Organic Chemistry, Vol. 70, Issue 2 https://doi.org/10.1021/jo048369k	journal	January 2005
Preparation of 4-Acetylamino-2,2,6,6-Tetramethylpiperidine-1-Oxoammonium Tetrafluoroborate, and the Oxidation of Geraniol to Geranial Bobbitt, James M.; Merbouh, Nabyl Organic Syntheses, Vol. 82, p. 80 https://doi.org/10.15227/orgsyn.082.0080	journal	January 2005
Aerobic Palladium-Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite Wickens, Zachary K.; Guzmán, Pablo E.; Grubbs, Robert H. Angewandte Chemie International Edition, Vol. 54, Issue 1 https://doi.org/10.1002/anie.201408650	journal	November 2014
Reactions of Nitric Oxide, Peroxynitrite, and Carbonate Radicals with Nitroxides and Their Corresponding Oxoammonium Cations Goldstein, Sara; Samuni, Amram; Merenyi, Gabor Chemical Research in Toxicology, Vol. 17, Issue 2 https://doi.org/10.1021/tx0342363	journal	February 2004
Electron transfer between azide and chlorine dioxide: the effect of solvent barrier nonadditivity Awad, H. H.; Stanbury, D. M. Journal of the American Chemical Society, Vol. 115, Issue 9 https://doi.org/10.1021/ja00062a030	journal	May 1993
Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen-Coupled Turnover Stahl, Shannon S. Angewandte Chemie International Edition, Vol. 43, Issue 26 https://doi.org/10.1002/anie.200300630	journal	June 2004
Redox equilibria of the nitrosonium cation and of its nonbonded complexes Lee, K. Y.; Kuchynka, D. J.; Kochi, Jay K. Inorganic Chemistry, Vol. 29, Issue 21 https://doi.org/10.1021/ic00346a008	journal	October 1990
Sustainable, mild and efficient p-methoxybenzyl ether deprotections utilizing catalytic DDQ Walsh, Katie; Sneddon, Helen F.; Moody, Christopher J. Tetrahedron, Vol. 70, Issue 40 https://doi.org/10.1016/j.tet.2014.07.003	journal	October 2014
Biphasic Synthesis of Hydrogen Peroxide from Carbon Monoxide, Water, and Oxygen Catalyzed by Palladium Complexes with Bidentate Nitrogen Ligands Bianchi, Daniele; Bortolo, Rossella; D'Aloisio, Rino Angewandte Chemie International Edition, Vol. 38, Issue 5 https://doi.org/10.1002/(SICI)1521-3773(19990301)38:5<706::AID-ANIE706>3.0.CO;2-G	journal	March 1999
Pulsradiolytische Beobachtungen über die Reduktion des NO ₃ ⁻ -Ions und über Bildung und Zerfall der persalpetrigen Säure in wäßriger Lösung Grätzel, M.; Henglein, A.; Taniguchi, S. Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 74, Issue 3 https://doi.org/10.1002/bbpc.19700740322	journal	March 1970
The NO2 absorption spectrum. I: Absorption cross-sections at ambient temperature in the 300?500 nm region M�rienne, M. F.; Jenouvrier, A.; Coquart, B. Journal of Atmospheric Chemistry, Vol. 20, Issue 3 https://doi.org/10.1007/BF00694498	journal	March 1995
The NO₂ Absorption Spectrum. IV: The 200–400 nm Region at 220 K Merienne, M. F.; Jenouvrier, A.; Coquart, B. Journal of Atmospheric Chemistry, Vol. 27, Issue 3, p. 219-232 https://doi.org/10.1023/A:1005829213463	journal	January 1997
Molecular Catalysts for Multielectron Redox Reactions of Small Molecules: The“Cofacial Metallodiporphyrin” Approach Collman, James P.; Wagenknecht, Paul S.; Hutchison, James E. Angewandte Chemie International Edition in English, Vol. 33, Issue 1516 https://doi.org/10.1002/anie.199415371	journal	September 1994
Electrocatalytic four-electron reduction of oxygen to water by a highly flexible cofacial cobalt bisporphyrin Chang, Christopher J.; Deng, Yongqi; Nocera, Daniel G. Chemical Communications, Issue 15 https://doi.org/10.1039/b001620i	journal	January 2000
Highly Efficient, Organocatalytic Aerobic Alcohol Oxidation Shibuya, Masatoshi; Osada, Yuji; Sasano, Yusuke Journal of the American Chemical Society, Vol. 133, Issue 17 https://doi.org/10.1021/ja110940c	journal	May 2011
A chemically regenerative redox fuel cell. II Kummer, J. T.; Oei, D. -G. Journal of Applied Electrochemistry, Vol. 15, Issue 4 https://doi.org/10.1007/BF01059304	journal	July 1985
Autoxidation kinetics of aqueous nitric oxide Ford, Peter C.; Wink, David A.; Stanbury, David M. FEBS Letters, Vol. 326, Issue 1-3 https://doi.org/10.1016/0014-5793(93)81748-O	journal	July 1993
Electroreduction of oxygen by pillared cobalt(II) cofacial diporphyrin catalysts Chang, C. K.; Liu, H. Y.; Abdalmuhdi, I. Journal of the American Chemical Society, Vol. 106, Issue 9 https://doi.org/10.1021/ja00321a055	journal	May 1984
ON THE THEORY OF OXIDATION—REDUCTION REACTIONS INVOLVING ELECTRON TRANSFER. V. COMPARISON AND PROPERTIES OF ELECTROCHEMICAL AND CHEMICAL RATE CONSTANTS ¹ Marcus, R. A. The Journal of Physical Chemistry, Vol. 67, Issue 4 https://doi.org/10.1021/j100798a033	journal	April 1963
Study of the Kinetics of Vanadium Redox Reaction by Rotating Disk Electrode Wu, Chun-Hsing; Liao, Hsin-Yi; Hsueh, Kan-Lin ECS Transactions, Vol. 35, Issue 32 https://doi.org/10.1149/1.3655684	journal	October 2011

Cited By (9)

Reaching Your Full (Over)Potential: A Novel Approach to Electrocatalytic Oxygen Reduction Knowles, Robert R. ACS Central Science, Vol. 1, Issue 5 https://doi.org/10.1021/acscentsci.5b00257	journal	August 2015
Ein Fest der Wissenschaft inmitten der Natur: Die 54. Bürgenstock‐Konferenz Baráth, Eszter; Mejía, Esteban Angewandte Chemie, Vol. 131, Issue 48 https://doi.org/10.1002/ange.201906781	journal	November 2019
Integrating TEMPO and Its Analogues with Visible-Light Photocatalysis Lang, Xianjun; Zhao, Jincai Chemistry - An Asian Journal, Vol. 13, Issue 6 https://doi.org/10.1002/asia.201701765	journal	February 2018
Studies on Effective Generation of Mediators Simultaneously at Both Half-Cells for VOC Degradation by Mediated Electroreduction and Mediated Electrooxidation Govindan, Muthuraman; Pillai, K. Chandrasekara; Subramanian, Balaji ACS Omega, Vol. 2, Issue 7 https://doi.org/10.1021/acsomega.7b00352	journal	July 2017
A Celebration of Science amidst Nature: The 54th Bürgenstock Conference Baráth, Eszter; Mejía, Esteban Angewandte Chemie International Edition, Vol. 58, Issue 48 https://doi.org/10.1002/anie.201906781	journal	November 2019
Copper nitrate: a privileged reagent for organic synthesis Gao, Mingchun; Ye, Rongxuan; Shen, Weijia Organic & Biomolecular Chemistry, Vol. 16, Issue 15 https://doi.org/10.1039/c8ob00332g	journal	January 2018
Ordered nanoporous lyotropic liquid crystal polymer resin for heterogeneous catalytic aerobic oxidation of alcohols Dwulet, Gregory E.; Gin, Douglas L. Chemical Communications, Vol. 54, Issue 85 https://doi.org/10.1039/c8cc05661g	journal	January 2018
Direct C(sp ² )−H Hydroxylation of Arenes with Palladium(II)/Oxygen Using Sulfoximines as a Recyclable Directing Group Das, Prasenjit; Guin, Joyram ChemCatChem, Vol. 10, Issue 11 https://doi.org/10.1002/cctc.201800064	journal	April 2018
Nitroxide Chemical Reactions Likhtenshtein, Gertz I. Nitroxides: Brief History, Fundamentals, and Recent Developments, p. 35-69 https://doi.org/10.1007/978-3-030-34822-9_3	book	January 2020

Similar Records

High-Potential Electrocatalytic O₂ Reduction with Nitroxyl/NO_x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis

Journal Article · Wed Jul 15 00:00:00 EDT 2015 · ACS Central Science · OSTI ID:1229947

Gerken, James B.; Stahl, Shannon S.

Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron–Proton Transfer Mediators

Journal Article · Wed Feb 12 00:00:00 EST 2020 · Accounts of Chemical Research · OSTI ID:1229947

Wang, Fei; Stahl, Shannon S.

Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron-Proton Transfer Mediators

Journal Article · Tue Mar 17 00:00:00 EDT 2020 · Accounts of Chemical Research · OSTI ID:1229947

Wang, Fei; Stahl, Shannon S.

Title: High-Potential Electrocatalytic O2 Reduction with Nitroxyl / NOx Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis

Citation Formats

References (94)

Cited By (9)

Similar Records

Related Subjects