Quinone 1 e – and 2 e – /2 H + Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships

Huynh, Mioy T.; Anson, Colin W.; Cavell, Andrew C.; Stahl, Shannon S.; Hammes-Schiffer, Sharon

doi:10.1021/jacs.6b05797

Quinone 1 e ^– and 2 e ^– /2 H ⁺ Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships

Journal Article · Thu Nov 10 04:00:00 EST 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b05797· OSTI ID:1339837

Huynh, Mioy T.; Anson, Colin W.; Cavell, Andrew C.; Stahl, Shannon S.; Hammes-Schiffer, Sharon

Quinones participate in diverse electron transfer and proton-coupled electron transfer processes in chemistry and biology. An experimental study of common quinones reveals a non-linear correlation between the 1 e^– and 2 e^–/2 H⁺ reduction potentials. This unexpected observation prompted a computational study of 128 different quinones, probing their 1 e^– reduction potentials, pKa values, and 2 e^–/2 H⁺ reduction potentials. The density functional theory calculations reveal an approximately linear correlation between these three properties and an effective Hammett constant associated with the quinone substituent(s). However, deviations from this linear scaling relationship are evident for quinones that feature halogen substituents, charged substituents, intramolecular hydrogen bonding in the hydroquinone, and/or sterically bulky substituents. These results, particularly the different substituent effects on the 1 e^– versus 2 e^– /2 H⁺ reduction potentials, have important implications for designing quinones with tailored redox properties.

Research Organization:: Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1339837

Report Number(s):: PNNL-SA--118838; KC0307010

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 49 Vol. 138; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (69)

Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide Song, Yang; Buettner, Garry R. Free Radical Biology and Medicine, Vol. 49, Issue 6 https://doi.org/10.1016/j.freeradbiomed.2010.05.009	journal	September 2010
Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals Becke, Axel D. The Journal of Chemical Physics, Vol. 107, Issue 20 https://doi.org/10.1063/1.475007	journal	November 1997
Self‐consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets Frisch, Michael J.; Pople, John A.; Binkley, J. Stephen The Journal of Chemical Physics, Vol. 80, Issue 7 https://doi.org/10.1063/1.447079	journal	April 1984
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model Barone, Vincenzo; Cossi, Maurizio The Journal of Physical Chemistry A, Vol. 102, Issue 11 https://doi.org/10.1021/jp9716997	journal	March 1998
Quantification of the Ambident Electrophilicities of Halogen-Substituted Quinones Guo, Xingwei; Mayr, Herbert Journal of the American Chemical Society, Vol. 136, Issue 32 https://doi.org/10.1021/ja505613b	journal	August 2014
Electrochemistry of ubiquinones: Menaquinones and plastoquinones in aprotic solvents Prince, Roger C.; Leslie Dutton, P.; Malcolm Bruce, J. FEBS Letters, Vol. 160, Issue 1-2 https://doi.org/10.1016/0014-5793(83)80981-8	journal	August 1983
Proton coupled electron transfer of ubiquinone Q2 incorporated in a self-assembled monolayer Lemmer, Celia; Bouvet, Marcel; Meunier-Prest, Rita Physical Chemistry Chemical Physics, Vol. 13, Issue 29 https://doi.org/10.1039/c0cp02700f	journal	January 2011
Mechanism of the oxidation of NADH by quinones. Energetics of one-electron and hydride routes Carlson, Brian W.; Miller, Larry L. Journal of the American Chemical Society, Vol. 107, Issue 2 https://doi.org/10.1021/ja00288a035	journal	January 1985
Efficient Dye-Sensitized Solar Cells Based on Hydroquinone/Benzoquinone as a Bioinspired Redox Couple Cheng, Ming; Yang, Xichuan; Zhang, Fuguo Angewandte Chemie International Edition, Vol. 51, Issue 39 https://doi.org/10.1002/anie.201205529	journal	September 2012
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Solvent dependence of the one-electron reduction of substituted benzo- and naphthoquinones Heffner, Janell E.; Wigal, Carl T.; Moe, Owen A. Electroanalysis, Vol. 9, Issue 8 https://doi.org/10.1002/elan.1140090810	journal	May 1997
A Metalloenzyme-Like Catalytic System for the Chemoselective Oxidative Cross-Coupling of Primary Amines to Imines under Ambient Conditions Largeron, Martine; Fleury, Maurice-Bernard Chemistry - A European Journal, Vol. 21, Issue 9 https://doi.org/10.1002/chem.201405843	journal	January 2015
Substituent Effects on Cobalt Diglyoxime Catalysts for Hydrogen Evolution Solis, Brian H.; Hammes-Schiffer, Sharon Journal of the American Chemical Society, Vol. 133, Issue 47 https://doi.org/10.1021/ja208091e	journal	November 2011
In situ coupled oxidation cycle catalyzed by highly active and reusable Pt-catalysts: dehydrogenative oxidation reactions in the presence of a catalytic amount of o-chloranil using molecular oxygen as the terminal oxidant Miyamura, Hiroyuki; Maehata, Kanako; Kobayashi, Shu Chemical Communications, Vol. 46, Issue 42 https://doi.org/10.1039/c0cc02865g	journal	January 2010
Pathway of proton transfer in bacterial reaction centers: replacement of serine-L223 by alanine inhibits electron and proton transfers associated with reduction of quinone to dihydroquinone. Paddock, M. L.; McPherson, P. H.; Feher, G. Proceedings of the National Academy of Sciences, Vol. 87, Issue 17 https://doi.org/10.1073/pnas.87.17.6803	journal	September 1990
Heterogeneous electron exchange of quinones in aprotic solvents Rüssel, C.; Janicke, W. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 199, Issue 1 https://doi.org/10.1016/0022-0728(86)87047-4	journal	February 1986
A Cooperative Catalytic System of Platinum/Iridium Alloyed Nanoclusters and a Dimeric Catechol Derivative: An Efficient Synthesis of Quinazolines Through a Sequential Aerobic Oxidative Process Yuan, Hao; Yoo, Woo-Jin; Miyamura, Hiroyuki Advanced Synthesis & Catalysis, Vol. 354, Issue 16 https://doi.org/10.1002/adsc.201200880	journal	October 2012
Bioinspired Organocatalytic Aerobic C–H Oxidation of Amines with an ortho -Quinone Catalyst Qin, Yan; Zhang, Long; Lv, Jian Organic Letters, Vol. 17, Issue 6 https://doi.org/10.1021/acs.orglett.5b00351	journal	March 2015
Hydrogen atom vs electron transfer in catecholase-mimetic oxidations by superoxometal complexes. Deuterium kinetic isotope effects Simándi, Tatiana M.; May, Zoltán; Szigyártó, Imola Cs. Dalton Trans., Issue 2 https://doi.org/10.1039/B412500B	journal	January 2005
The influence of ion-association on the polarography of quinones in dimethylformamide Peover, M. E.; Davies, J. D. Journal of Electroanalytical Chemistry (1959), Vol. 6, Issue 1 https://doi.org/10.1016/0022-0728(63)80116-3	journal	July 1963
Theoretical Analysis of Mechanistic Pathways for Hydrogen Evolution Catalyzed by Cobaloximes Solis, Brian H.; Hammes-Schiffer, Sharon Inorganic Chemistry, Vol. 50, Issue 21 https://doi.org/10.1021/ic201842v	journal	November 2011
Chemoselective Organocatalytic Aerobic Oxidation of Primary Amines to Secondary Imines Wendlandt, Alison E.; Stahl, Shannon S. Organic Letters, Vol. 14, Issue 11 https://doi.org/10.1021/ol301095j	journal	May 2012
Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21+G basis set for first-row elements, Li-F Clark, Timothy; Chandrasekhar, Jayaraman; Spitznagel, G�nther W. Journal of Computational Chemistry, Vol. 4, Issue 3 https://doi.org/10.1002/jcc.540040303	journal	October 1983
Computational design of molecules for an all-quinone redox flow battery Er, Süleyman; Suh, Changwon; Marshak, Michael P. Chemical Science, Vol. 6, Issue 2, p. 885-893 https://doi.org/10.1039/C4SC03030C	journal	January 2015
Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements Francl, Michelle M.; Pietro, William J.; Hehre, Warren J. The Journal of Chemical Physics, Vol. 77, Issue 7, p. 3654-3665 https://doi.org/10.1063/1.444267	journal	October 1982
A Biologically Inspired Cu ^I /Topaquinone-Like Co-Catalytic System for the Highly Atom-Economical Aerobic Oxidation of Primary Amines to Imines Largeron, Martine; Fleury, Maurice-Bernard Angewandte Chemie International Edition, Vol. 51, Issue 22 https://doi.org/10.1002/anie.201200587	journal	April 2012
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
Using Cyclic Voltammetry and Molecular Modeling To Determine Substituent Effects in the One-Electron Reduction of Benzoquinones Heffner, Janell E.; Raber, Jeffrey C.; Moe, Owen A. Journal of Chemical Education, Vol. 75, Issue 3 https://doi.org/10.1021/ed075p365	journal	March 1998
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 density functional study of van der Waals interactions Kamiya, Muneaki; Tsuneda, Takao; Hirao, Kimihiko The Journal of Chemical Physics, Vol. 117, Issue 13 https://doi.org/10.1063/1.1501132	journal	October 2002
Electrochemistry of potentially bioreductive alkylating quinones Driebergen, R. J.; Moret, E. E.; Janssen, L. H. M. Analytica Chimica Acta, Vol. 257, Issue 2 https://doi.org/10.1016/0003-2670(92)85179-A	journal	February 1992
Proton-Coupled Electron Transfer Huynh, My Hang V.; Meyer, Thomas J. Chemical Reviews, Vol. 107, Issue 11 https://doi.org/10.1021/cr0500030	journal	November 2007
Aerobic Oxidation of Hydroquinone Derivatives Catalyzed by Polymer-Incarcerated Platinum Catalyst Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke Angewandte Chemie International Edition, Vol. 47, Issue 42 https://doi.org/10.1002/anie.200802192	journal	October 2008
Modular o -Quinone Catalyst System for Dehydrogenation of Tetrahydroquinolines under Ambient Conditions Wendlandt, Alison E.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 136, Issue 34 https://doi.org/10.1021/ja506546w	journal	August 2014
Ab Initio Calculations of Thermodynamic Hydricities of Transition-Metal Hydrides in Acetonitrile Qi, Xiu-Juan; Fu, Yao; Liu, Lei Organometallics, Vol. 26, Issue 17 https://doi.org/10.1021/om0702429	journal	August 2007
Dispersion and repulsion contributions to the solvation energy: Refinements to a simple computational model in the continuum approximation Floris, F. M.; Tomasi, J.; Ahuir, J. L. Pascual Journal of Computational Chemistry, Vol. 12, Issue 7 https://doi.org/10.1002/jcc.540120703	journal	September 1991
Possible molecular mechanisms of the protonmotive function of cytochrome systems Mitchell, Peter Journal of Theoretical Biology, Vol. 62, Issue 2 https://doi.org/10.1016/0022-5193(76)90124-7	journal	October 1976
Substituent Effect on a Family of Quinones in Aprotic Solvents: An Experimental and Theoretical Approach Frontana, Carlos; Vázquez-Mayagoitia, Álvaro; Garza, Jorge The Journal of Physical Chemistry A, Vol. 110, Issue 30 https://doi.org/10.1021/jp060836+	journal	July 2006
Evaluation of the dispersion contribution to the solvation energy. A simple computational model in the continuum approximation Floris, F.; Tomasi, J. Journal of Computational Chemistry, Vol. 10, Issue 5 https://doi.org/10.1002/jcc.540100504	journal	July 1989
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/PhysRevA.38.3098	journal	September 1988
Co(salophen)-Catalyzed Aerobic Oxidation of p -Hydroquinone: Mechanism and Implications for Aerobic Oxidation Catalysis Anson, Colin W.; Ghosh, Soumya; Hammes-Schiffer, Sharon Journal of the American Chemical Society, Vol. 138, Issue 12 https://doi.org/10.1021/jacs.6b00254	journal	March 2016
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
Computing Free Energy Landscapes: Application to Ni-based Electrocatalysts with Pendant Amines for H ₂ Production and Oxidation Chen, Shentan; Ho, Ming-Hsun; Bullock, R. Morris ACS Catalysis, Vol. 4, Issue 1 https://doi.org/10.1021/cs401104w	journal	December 2013
Discovery of a Metalloenzyme-like Cooperative Catalytic System of Metal Nanoclusters and Catechol Derivatives for the Aerobic Oxidation of Amines Yuan, Hao; Yoo, Woo-Jin; Miyamura, Hiroyuki Journal of the American Chemical Society, Vol. 134, Issue 34 https://doi.org/10.1021/ja306934b	journal	August 2012
Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni Journal of Computational Chemistry, Vol. 24, Issue 6 https://doi.org/10.1002/jcc.10189	journal	April 2003
A Bio-Inspired, Small Molecule Electron-Coupled-Proton Buffer for Decoupling the Half-Reactions of Electrolytic Water Splitting Rausch, Benjamin; Symes, Mark D.; Cronin, Leroy Journal of the American Chemical Society, Vol. 135, Issue 37 https://doi.org/10.1021/ja4071893	journal	September 2013
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst Wendlandt, Alison E.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 136, Issue 1 https://doi.org/10.1021/ja411692v	journal	December 2013
Substituent effects on the stabilities of phenoxyl radicals and the acidities of phenoxyl radical cations Bordwell, Frederick G.; Cheng, Jinpei Journal of the American Chemical Society, Vol. 113, Issue 5 https://doi.org/10.1021/ja00005a042	journal	February 1991
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Theoretical Analysis of the Sequential Proton-Coupled Electron Transfer Mechanisms for H ₂ Oxidation and Production Pathways Catalyzed by Nickel Molecular Electrocatalysts Fernandez, Laura E.; Horvath, Samantha; Hammes-Schiffer, Sharon The Journal of Physical Chemistry C, Vol. 116, Issue 4 https://doi.org/10.1021/jp210690q	journal	January 2012
Novel Catalysis of Hydroquinone Autoxidation with Nitrogen Oxides Bosch, E.; Rathore, R.; Kochi, J. K. The Journal of Organic Chemistry, Vol. 59, Issue 9 https://doi.org/10.1021/jo00088a039	journal	May 1994
Photobasicity in Quinolines: Origin and Tunability via the Substituents’ Hammett Parameters Driscoll, Eric William; Hunt, Jonathan Ryan; Dawlaty, Jahan M. The Journal of Physical Chemistry Letters, Vol. 7, Issue 11 https://doi.org/10.1021/acs.jpclett.6b00790	journal	May 2016
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
Self‐Consistent Molecular‐Orbital Methods. IX. An Extended Gaussian‐Type Basis for Molecular‐Orbital Studies of Organic Molecules Ditchfield, R.; Hehre, W. J.; Pople, J. A. The Journal of Chemical Physics, Vol. 54, Issue 2 https://doi.org/10.1063/1.1674902	journal	January 1971
Quinone-Catalyzed Selective Oxidation of Organic Molecules Wendlandt, Alison E.; Stahl, Shannon S. Angewandte Chemie International Edition, Vol. 54, Issue 49 https://doi.org/10.1002/anie.201505017	journal	November 2015
Mechanisms of Hydride Abstractions by Quinones Guo, Xingwei; Zipse, Hendrik; Mayr, Herbert Journal of the American Chemical Society, Vol. 136, Issue 39 https://doi.org/10.1021/ja507598y	journal	September 2014
Microbial ubiquinones: multiple roles in respiration, gene regulation and oxidative stress management Søballe, Britta; Poole, Robert K. Microbiology, Vol. 145, Issue 8 https://doi.org/10.1099/13500872-145-8-1817	journal	August 1999
A survey of Hammett substituent constants and resonance and field parameters Hansch, Corwin.; Leo, A.; Taft, R. W. Chemical Reviews, Vol. 91, Issue 2 https://doi.org/10.1021/cr00002a004	journal	March 1991
High-Potential Electrocatalytic O ₂ Reduction with Nitroxyl/NO _x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis Gerken, James B.; Stahl, Shannon S. ACS Central Science, Vol. 1, Issue 5 https://doi.org/10.1021/acscentsci.5b00163	journal	July 2015
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
Dioxygen Reduction by a Pd(0)–Hydroquinone Diphosphine Complex Horak, Kyle T.; Agapie, Theodor Journal of the American Chemical Society, Vol. 138, Issue 10 https://doi.org/10.1021/jacs.5b12928	journal	March 2016
Semiempirical GGA-type density functional constructed with a long-range dispersion correction Grimme, Stefan Journal of Computational Chemistry, Vol. 27, Issue 15, p. 1787-1799 https://doi.org/10.1002/jcc.20495	journal	January 2006
van der Waals Volumes and Radii Bondi, A. The Journal of Physical Chemistry, Vol. 68, Issue 3, p. 441-451 https://doi.org/10.1021/j100785a001	journal	March 1964
Density-functional approximation for the correlation energy of the inhomogeneous electron gas Perdew, John P. Physical Review B, Vol. 33, Issue 12 https://doi.org/10.1103/PhysRevB.33.8822	journal	June 1986
A scaled particle theory of aqueous and nonaqueous solutions Pierotti, Robert A. Chemical Reviews, Vol. 76, Issue 6 https://doi.org/10.1021/cr60304a002	journal	December 1976
Oxidation of Unactivated Primary Aliphatic Amines Catalyzed by an Electrogenerated 3,4-Azaquinone Species: A Small-Molecule Mimic of Amine Oxidases Largeron, Martine; Neudorffer, Anne; Fleury, Maurice-Bernard Angewandte Chemie International Edition, Vol. 42, Issue 9 https://doi.org/10.1002/anie.200390263	journal	March 2003
A metal-free organic–inorganic aqueous flow battery Huskinson, Brian; Marshak, Michael P.; Suh, Changwon Nature, Vol. 505, Issue 7482, p. 195-198 https://doi.org/10.1038/nature12909	journal	January 2014

Cited By (24)

Uncatalyzed Oxidative C−H Amination of 9,10‐Dihydro‐9‐Heteroanthracenes: A Mechanistic Study van Leest, Nicolaas P.; Grooten, Lars; van der Vlugt, Jarl Ivar Chemistry – A European Journal, Vol. 25, Issue 23 https://doi.org/10.1002/chem.201900377	journal	March 2019
Design and synthesis of functionalized coordination polymers as recyclable heterogeneous photocatalysts Ye, Cai-Ping; Xu, Gan; Wang, Zheng Dalton Transactions, Vol. 47, Issue 18 https://doi.org/10.1039/c8dt00902c	journal	January 2018
Toward High‐Voltage, Energy‐Dense, and Durable Aqueous Organic Redox Flow Batteries: Role of the Supporting Electrolytes Chen, Ruiyong ChemElectroChem, Vol. 6, Issue 3 https://doi.org/10.1002/celc.201801505	journal	September 2018
Palladium-Catalyzed C-H Functionalization of Amido-Substitued 1,4-Napthoquinone in the Presence of Amines toward the Formation of Pyrroles and Imidazoles Chen, Szu-Wei; Hong, Fung-E ChemistrySelect, Vol. 2, Issue 31 https://doi.org/10.1002/slct.201702173	journal	October 2017
Electrochemical characterization of natural organic matter by direct voltammetry in an aprotic solvent Pavitt, Ania S.; Tratnyek, Paul G. Environmental Science: Processes & Impacts, Vol. 21, Issue 10 https://doi.org/10.1039/c9em00313d	journal	January 2019
Redox‐Active Guanidines in Proton‐Coupled Electron‐Transfer Reactions: Real Alternatives to Benzoquinones? Wild, Ute; Hübner, Olaf; Himmel, Hans‐Jörg Chemistry – A European Journal, Vol. 25, Issue 70 https://doi.org/10.1002/chem.201903438	journal	October 2019
Diversity and uniformity in anion–π complexes of thiocyanate with aromatic, olefinic and quinoidal π-acceptors Wilson, Joshua; Maxson, Tristan; Wright, Isabelle Dalton Transactions, Vol. 49, Issue 25 https://doi.org/10.1039/d0dt01654c	journal	January 2020
Multi‐electron Reduction Capacity and Multiple Binding Pockets in Metal–Organic Redox Assembly at Surfaces Morris, Tobias W.; Huerfano, I. J.; Wang, Miao Chemistry – A European Journal, Vol. 25, Issue 21 https://doi.org/10.1002/chem.201900002	journal	March 2019
Mapping the frontiers of quinone stability in aqueous media: implications for organic aqueous redox flow batteries Tabor, Daniel P.; Gómez-Bombarelli, Rafael; Tong, Liuchuan Journal of Materials Chemistry A, Vol. 7, Issue 20 https://doi.org/10.1039/c9ta03219c	journal	January 2019
Systematic High-Accuracy Prediction of Electron Affinities for Biological Quinones: Systematic High-Accuracy Prediction of Electron Affinities for Biological Quinones Schulz, Christine E.; Dutta, Achintya Kumar; Izsák, Róbert Journal of Computational Chemistry, Vol. 39, Issue 29 https://doi.org/10.1002/jcc.25570	journal	October 2018
Electrophotocatalytic S _N Ar Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base Huang, He; Lambert, Tristan H. Angewandte Chemie, Vol. 132, Issue 2 https://doi.org/10.1002/ange.201909983	journal	November 2019
Deactivation of Co-Schiff base catalysts in the oxidation of para -substituted lignin models for the production of benzoquinones Zuleta, Ernesto C.; Goenaga, Gabriel A.; Zawodzinski, Thomas A. Catalysis Science & Technology, Vol. 10, Issue 2 https://doi.org/10.1039/c9cy02040c	journal	January 2020
Photoredox-Switchable Resorcin[4]arene Cavitands: Radical Control of Molecular Gripping Machinery via Hydrogen Bonding Milić, Jovana; Zalibera, Michal; Talaat, Darius Chemistry - A European Journal, Vol. 24, Issue 6 https://doi.org/10.1002/chem.201704788	journal	December 2017
Electrophotocatalytic S _N Ar Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base Huang, He; Lambert, Tristan H. Angewandte Chemie International Edition, Vol. 59, Issue 2 https://doi.org/10.1002/anie.201909983	journal	January 2020
Syntheses, crystal structures and photocatalytic properties of transition metal complexes based on 9,10-anthraquinone-1,3-dicarboxylate Ye, Cai-Ping; Ling, Rong; Yang, Lin-Feng Transition Metal Chemistry, Vol. 44, Issue 5 https://doi.org/10.1007/s11243-019-00334-2	journal	June 2019
Intermolecular Interactions between Halogen‐Substituted p ‐Benzoquinones and Halide Anions: Anion‐π Complexes versus Halogen Bonding Jalilov, Almaz; Deats, Spencer; Albukhari, Muath ChemPlusChem, Vol. 85, Issue 3 https://doi.org/10.1002/cplu.202000012	journal	March 2020
Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions Ortiz‐Rojano, Laura; Rojas‐Martín, Jaime; Rodríguez‐Diaz, Ciro Chemistry – A European Journal, Vol. 25, Issue 66 https://doi.org/10.1002/chem.201904138	journal	October 2019
Probing the Proton‐Coupled Electron‐Transfer (PCET) Reactivity of a Cross‐Conjugated Cruciform Chromophore by Redox‐State‐Dependent Fluorescence Wagner, Conrad; Hübner, Olaf; Kaifer, Elisabeth Chemistry – A European Journal, Vol. 25, Issue 15 https://doi.org/10.1002/chem.201900268	journal	February 2019
Stable, Dual Redox Unit Organic Electrodes An, So Young; Schon, Tyler B.; Seferos, Dwight S. ACS Omega, Vol. 5, Issue 2 https://doi.org/10.1021/acsomega.9b03355	journal	January 2020
C-H Bond Functionalization of 1,4-Benzoquinone by Silver-Mediated Regioselective Phosphination and Amination Reactions: C-H Bond Functionalization of 1,4-Benzoquinone by Silver-Mediated Regioselective Phosphination and Amination Reactions Chang, Yu-Chang; Yuan, Pin-Ting; Hong, Fung-E European Journal of Organic Chemistry, Vol. 2017, Issue 17 https://doi.org/10.1002/ejoc.201700109	journal	May 2017
Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones Gerken, James B.; Stamoulis, Alexios; Suh, Sung-Eun Chemical Communications, Vol. 56, Issue 8 https://doi.org/10.1039/c9cc08878d	journal	January 2020
A Stereodynamic Redox‐Interconversion Network of Vicinal Tertiary and Quaternary Carbon Stereocenters in Hydroquinone–Quinone Hybrid Dihydrobenzofurans Storch, Golo; Kim, Byoungmoo; Mercado, Brandon Q. Angewandte Chemie, Vol. 130, Issue 46 https://doi.org/10.1002/ange.201808305	journal	October 2018
Electron transfer in complexes of B ^II cations with organic π-acceptors: a combined experimental and quantum-chemical study Vogler, Daniel; Wolf, Nina; Kaifer, Elisabeth Dalton Transactions, Vol. 48, Issue 38 https://doi.org/10.1039/c9dt03151k	journal	January 2019
A Stereodynamic Redox‐Interconversion Network of Vicinal Tertiary and Quaternary Carbon Stereocenters in Hydroquinone–Quinone Hybrid Dihydrobenzofurans Storch, Golo; Kim, Byoungmoo; Mercado, Brandon Q. Angewandte Chemie International Edition, Vol. 57, Issue 46 https://doi.org/10.1002/anie.201808305	journal	November 2018

Similar Records

Quinone 1 e^– and 2 e^–/2 H⁺ Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships

Journal Article · Wed Nov 09 19:00:00 EST 2016 · Journal of the American Chemical Society · OSTI ID:1388875

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY