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.; Elder, Thomas; Bozell, Joseph J.

doi:10.1039/c9cy02040c

Title: Deactivation of Co-Schiff base catalysts in the oxidation of para-substituted lignin models for the production of benzoquinones

Journal Article · Fri Dec 06 00:00:00 UTC 2019 · Catalysis Science and Technology

DOI: https://doi.org/10.1039/c9cy02040c · OSTI ID:1799149

^[1]; Goenaga, Gabriel A. ^[2]; Zawodzinski, Thomas A. ^[3]; Elder, Thomas ^[4];

^[5]

Univ. of Tennessee, Knoxville, TN (United States). Center for Renewable Carbon. Bredesen Center for Interdisciplinary Research and Education; OSTI
Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemical and Biomolecular Engineering
Univ. of Tennessee, Knoxville, TN (United States). Bredesen Center for Interdisciplinary Research and Education. Dept. of Chemical and Biomolecular Engineering
USDA Forest Service, Southern Research Station, Auburn, AL (United States)
Univ. of Tennessee, Knoxville, TN (United States). Center for Renewable Carbon. Bredesen Center for Interdisciplinary Research and Education

The effect of quinones on the deactivation of four- and five-coordinate Co-Schiff base catalysts used for the oxidation of lignin models is systematically studied. 2,6-Dimethoxy-1,4-benzoquinone does not affect the catalytic activity of any of the studied Co-Schiff base catalysts, but 1,4-benzoquinone and 2-methoxy-1,4-benzoquinone have a strong effect on the catalytic activity. Quinone solubility in the reaction solvent does not correlate with catalyst deactivation, but added pyridine (a basic axial ligand) promotes catalyst deactivation by quinone. The synthesis and characterization of a catalytically inactive Co-Schiff base-quinone complex is presented and preliminary computational analysis of this complex in comparison to a dimeric Co-Schiff base peroxo complex is also discussed. Quinone and the Co-Schiff base redox potentials are found to correlate with catalyst deactivation. Thus, catalysts with a lower redox potential were more susceptible to deactivation, and quinones with a higher redox potential deactivate the catalysts. Based on these results, two mechanisms for deactivation of the catalyst are proposed. The first mechanism describes how the formation a Co-Schiff base-quinone complex prevents formation of the key catalytically active Co-superoxo complex. The second proposed mechanism suggests that quinones inhibit the Co-Schiff base catalyst by scavenging intermediate Co-superoxo radicals.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Northeastern Univ., Boston, MA (United States); Purdue Univ., West Lafayette, IN (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio) (EFRC)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Fuel Cell Technologies Office; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: EE0000459; SC0000997

OSTI ID:: 1799149

Journal Information:: Catalysis Science and Technology, Journal Name: Catalysis Science and Technology Journal Issue: 2 Vol. 10; ISSN 2044-4753

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (105)

Activation of Molecular Oxygen Henrici-Olivé, G.; Olivé, S. Angewandte Chemie International Edition in English, Vol. 13, Issue 1 https://doi.org/10.1002/anie.197400291	journal	January 1974
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
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
Proton Transfer versus Hydrogen Bonding: The Reduction of Ubiquinone Q ₂ Incorporated in a Self-Assembled Monolayer in Unbuffered Aqueous Solution Liehn, Cédric; Bouvet, Marcel; Meunier-Prest, Rita ChemElectroChem, Vol. 1, Issue 12 https://doi.org/10.1002/celc.201402191	journal	September 2014
π-Bonded Quinonoid Transition-Metal Complexes Reingold, Jeffrey A.; Son, Seung Uk; Kim, Sang Bok ChemInform, Vol. 37, Issue 37 https://doi.org/10.1002/chin.200637207	journal	September 2006
Mechanistic Insights into the Oxidation of Veratryl Alcohol with Co(salen) and Oxygen in Aqueous Media: An in-situ Spectroscopic Study Kervinen, Kaisa; Korpi, Heikki; Gerbrand Mesu, J. European Journal of Inorganic Chemistry, Vol. 2005, Issue 13 https://doi.org/10.1002/ejic.200500042	journal	July 2005
Singlet Oxygen and Superoxide: Experimental Differentiation and Analysis Maurette, Marie-Th�r�se; Oliveros, Esther; Infelta, Pierre P. Helvetica Chimica Acta, Vol. 66, Issue 2 https://doi.org/10.1002/hlca.19830660236	journal	March 1983
Guidelines for accurate EC50/IC50 estimation Sebaugh, J. L. Pharmaceutical Statistics, Vol. 10, Issue 2 https://doi.org/10.1002/pst.426	journal	March 2011
Free Radical Scavenging Reactions of Tetrahydroxyquinone: A Pulse Radiolysis Study Joshi, Ravi ChemistrySelect, Vol. 1, Issue 5 https://doi.org/10.1002/slct.201600030	journal	April 2016
The Catalytic Efficacy of Co(salen)(AL) in O2 Oxidation Reactions in CO2-Expanded Solvent Media: Axial Ligand Dependence and Substrate Selectivity Rajagopalan, Bhuma; Cai, Hu; Busch, Daryle H. Catalysis Letters, Vol. 123, Issue 1-2 https://doi.org/10.1007/s10562-007-9379-z	journal	January 2008
Formation of semiquinone radical anion and free radical scavenging reactions of plumbagin: a pulse radiolysis study Joshi, Ravi; Gangabhagirathi, R. Journal of Radioanalytical and Nuclear Chemistry, Vol. 303, Issue 1 https://doi.org/10.1007/s10967-014-3501-7	journal	September 2014
The chemical and biological activities of quinones: overview and implications in analytical detection El-Najjar, Nahed; Gali-Muhtasib, Hala; Ketola, Raimo A. Phytochemistry Reviews, Vol. 10, Issue 3 https://doi.org/10.1007/s11101-011-9209-1	journal	April 2011
Are quinones producers or scavengers of superoxide ion in cells? Afanas'ev, Igor B.; Korkina, Ludmila G.; Suslova, Tatjana B. Archives of Biochemistry and Biophysics, Vol. 281, Issue 2 https://doi.org/10.1016/0003-9861(90)90439-6	journal	September 1990
Utilization of O2 for the specific oxidation of organic substrates with cobalt(II) catalysts Bailey, Cynthia L.; Drago, Russell S. Coordination Chemistry Reviews, Vol. 79, Issue 3 https://doi.org/10.1016/0010-8545(87)80009-7	journal	July 1987
The transition metal coordination chemistry of anion radicals Kaim, Wolfgang Coordination Chemistry Reviews, Vol. 76 https://doi.org/10.1016/0010-8545(87)85004-X	journal	February 1987
Reaction of superoxo Co(III) complex with quinones formation of a semiquinone Co(III) complex Nishinaga, A.; Tomita, H.; Matsuura, T. Tetrahedron Letters, Vol. 21, Issue 50 https://doi.org/10.1016/0040-4039(80)80157-2	journal	January 1980
Field Control of Regioselectivity in CoIII(salpr)(OH) Promoted Oxygenation of 4-Aryl-2,6-di-tert-butylphenols Yano, M. Tetrahedron Letters, Vol. 36, Issue 32 https://doi.org/10.1016/00404-0399(50)10994-	journal	August 1995
Redox and addition chemistry of quinoid compounds and its biological implications Brunmark, Anders; Cadenas, Enrique Free Radical Biology and Medicine, Vol. 7, Issue 4 https://doi.org/10.1016/0891-5849(89)90126-3	journal	January 1989
Recent developments in the studies of molecular oxygen adducts of cobalt (II) compounds and related systems Smith, Thomas D.; Pilbrow, John R. Coordination Chemistry Reviews, Vol. 39, Issue 3 https://doi.org/10.1016/S0010-8545(00)80509-3	journal	December 1981
Oxidative addition of quinones to planar cobalt(II) dithiolato, dithioacetylacetonato and Schiff-base complexes Hartl, F.; Vlček, A. Inorganica Chimica Acta, Vol. 118, Issue 1 https://doi.org/10.1016/S0020-1693(00)86407-5	journal	August 1986
The redox reactions of complex cobalt(II) cyanides. XI. The kinetics and mechanism of the redox addition reaction of pentacyanocobaltate(II) with 1,4-naphthoquinone in aqueous solution Fiala, J.; Vlček, A. A. Inorganica Chimica Acta, Vol. 42 https://doi.org/10.1016/S0020-1693(00)88890-8	journal	January 1980
Reaction of pentacyanocobaltate(II) with derivatives of p-benzoquinone Hanzlík, J.; Vlček, A. A. Inorganica Chimica Acta, Vol. 8 https://doi.org/10.1016/S0020-1693(00)92623-9	journal	January 1974
Decomposition pathways of homogeneous catalysts van Leeuwen, Piet W. N. M. Applied Catalysis A: General, Vol. 212, Issue 1-2 https://doi.org/10.1016/S0926-860X(00)00844-9	journal	April 2001
Reaction of radicals with benzoquinone—addition or electron transfer? Maroz, A.; Brede, O. Radiation Physics and Chemistry, Vol. 67, Issue 3-4 https://doi.org/10.1016/S0969-806X(03)00051-3	journal	June 2003
Recent advances in transition-metal-catalyzed selective oxidation of substituted phenols and methoxyarenes with environmentally benign oxidants Kholdeeva, Oxana A.; Zalomaeva, Olga V. Coordination Chemistry Reviews, Vol. 306 https://doi.org/10.1016/j.ccr.2015.07.019	journal	January 2016
Aerobic oxidation of benzyl alcohol to benzaldehyde catalyzed by carbon nanotubes without any promoter Luo, Jin; Yu, Hao; Wang, Hongjuan Chemical Engineering Journal, Vol. 240 https://doi.org/10.1016/j.cej.2013.11.093	journal	March 2014
The stabilizing role of intramolecular hydrogen bonding in disubstituted hydroxy-quinones Armendáriz-Vidales, Georgina; Martínez-González, Eduardo; Cuevas-Fernández, Héctor Javier Electrochimica Acta, Vol. 110 https://doi.org/10.1016/j.electacta.2013.05.123	journal	November 2013
Back-reactions, short-circuits, leaks and other energy wasteful reactions in biological electron transfer: Redox tuning to survive life in O ₂ Rutherford, A. William; Osyczka, Artur; Rappaport, Fabrice FEBS Letters, Vol. 586, Issue 5 https://doi.org/10.1016/j.febslet.2011.12.039	journal	January 2012
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
Electronic and steric effects in cobalt Schiff bases complexes: Synthesis, characterization and catalytic activity of some cobalt(II) tetra-halogens-dimethyl salen complexes Pui, Aurel; Policar, Clotilde; Mahy, Jean-Pierre Inorganica Chimica Acta, Vol. 360, Issue 6 https://doi.org/10.1016/j.ica.2006.10.040	journal	April 2007
The electrochemical reduction of 1,4-benzoquinone in 1-ethyl-3-methylimidazolium bis(trifluoromethane-sulfonyl)-imide, [C2mim][NTf2]: A voltammetric study of the comproportionation between benzoquinone and the benzoquinone dianion Wang, Yijun; Rogers, Emma I.; Belding, Stephen R. Journal of Electroanalytical Chemistry, Vol. 648, Issue 2 https://doi.org/10.1016/j.jelechem.2010.07.016	journal	October 2010
Formation of semiquinone radical in the reaction of embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone) with reductants as well as oxidants. Characterization by pulse radiolysis and structure investigation by quantum chemical study Joshi, Ravi; Ghanty, Tapan K.; Mukherjee, Tulsi Journal of Molecular Structure, Vol. 928, Issue 1-3 https://doi.org/10.1016/j.molstruc.2009.03.010	journal	June 2009
Synthesis, characterization and catalytic activity of halo-methyl-bis(salicylaldehyde)ethylenediamine cobalt(II) complexes Pui, Aurel; Mahy, Jean-Pierre Polyhedron, Vol. 26, Issue 13 https://doi.org/10.1016/j.poly.2007.02.030	journal	August 2007
Steric effects of bulky tethered arylpiperazines on the reactivity of Co-Schiff base oxidation catalysts—a synthetic and computational study Key, Rebecca E.; Elder, Thomas; Bozell, Joseph J. Tetrahedron, Vol. 75, Issue 23 https://doi.org/10.1016/j.tet.2019.04.059	journal	June 2019
Catalytic oxidation of para-substituted phenols with cobalt–Schiff base complexes/O2—selective conversion of syringyl and guaiacyl lignin models to benzoquinones Cedeno, Diana; Bozell, Joseph J. Tetrahedron Letters, Vol. 53, Issue 19 https://doi.org/10.1016/j.tetlet.2012.02.093	journal	May 2012
Superoxide Ion: Generation and Chemical Implications Hayyan, Maan; Hashim, Mohd Ali; AlNashef, Inas M. Chemical Reviews, Vol. 116, Issue 5 https://doi.org/10.1021/acs.chemrev.5b00407	journal	February 2016
Iron-Mediated Oxidation of Methoxyhydroquinone under Dark Conditions: Kinetic and Mechanistic Insights Yuan, Xiu; Davis, James A.; Nico, Peter S. Environmental Science & Technology, Vol. 50, Issue 4 https://doi.org/10.1021/acs.est.5b03939	journal	January 2016
Kinetic Stabilization of Quinone Dianions via Hydrogen Bonding by Water in Aprotic Solvents Staley, Patrick A.; Lopez, Eric M.; Clare, Laurie A. The Journal of Physical Chemistry C, Vol. 119, Issue 35 https://doi.org/10.1021/acs.jpcc.5b06323	journal	August 2015
Photocatalytic Cleavage of C–C Bond in Lignin Models under Visible Light on Mesoporous Graphitic Carbon Nitride through π–π Stacking Interaction Liu, Huifang; Li, Hongji; Lu, Jianmin ACS Catalysis, Vol. 8, Issue 6 https://doi.org/10.1021/acscatal.8b00022	journal	April 2018
Progress toward Lignin Valorization via Selective Catalytic Technologies and the Tailoring of Biosynthetic Pathways Key, Rebecca E.; Bozell, Joseph J. ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 10 https://doi.org/10.1021/acssuschemeng.6b01319	journal	August 2016
Spin-pairing model of dioxygen binding and its application to various transition-metal systems as well as hemoglobin cooperativity Drago, Russell S.; Corden, Barry B. Accounts of Chemical Research, Vol. 13, Issue 10 https://doi.org/10.1021/ar50154a003	journal	October 1980
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
Update 1 of: Electrochemical Approach to the Mechanistic Study of Proton-Coupled Electron Transfer Costentin, Cyrille; Robert, Marc; Savéant, Jean-Michel Chemical Reviews, Vol. 110, Issue 12 https://doi.org/10.1021/cr100038y	journal	December 2010
Deactivation in Homogeneous Transition Metal Catalysis: Causes, Avoidance, and Cure Crabtree, Robert H. Chemical Reviews, Vol. 115, Issue 1 https://doi.org/10.1021/cr5004375	journal	November 2014
Synthetic oxygen carriers related to biological systems Jones, Robert D.; Summerville, David A.; Basolo, Fred. Chemical Reviews, Vol. 79, Issue 2 https://doi.org/10.1021/cr60318a002	journal	April 1979
Enhanced Photocatalytic Removal of Sodium Pentachlorophenate with Self-Doped Bi ₂ WO ₆ under Visible Light by Generating More Superoxide Ions Ding, Xing; Zhao, Kun; Zhang, Lizhi Environmental Science & Technology, Vol. 48, Issue 10 https://doi.org/10.1021/es405714q	journal	May 2014
Autoxidation of Substituted Phenols Catalyzed by Cobalt Schiff Base Complexes in Supercritical Carbon Dioxide Musie, Ghezai T.; Wei, Ming; Subramaniam, Bala Inorganic Chemistry, Vol. 40, Issue 14 https://doi.org/10.1021/ic001288w	journal	July 2001
Oxygenation of Substituted Phenols Using Molecular Oxygen and Cobalt(II) Cyclidene Complexes Deng, Yanpei; Busch, Daryle H. Inorganic Chemistry, Vol. 34, Issue 25 https://doi.org/10.1021/ic00129a024	journal	December 1995
Iron(III) complexes with semiquinone and hydroquinone ligands Tuchagues, Jean Pierre M.; Hendrickson, David N. Inorganic Chemistry, Vol. 22, Issue 18 https://doi.org/10.1021/ic00160a016	journal	August 1983
Metallotetraphenylporphyrin-catalyzed oxidation of 2,6-di-tert-butylphenol Wang, Xian Yuan; Motekaitis, Ramunas J.; Martell, Arthur E. Inorganic Chemistry, Vol. 23, Issue 3 https://doi.org/10.1021/ic00171a004	journal	February 1984
Unusual ligand field effects in square-planar cobalt(II) complexes of quadridentate Schiff bases Ceulemans, A.; Dendooven, M.; Vanquickenborne, L. G. Inorganic Chemistry, Vol. 24, Issue 8 https://doi.org/10.1021/ic00202a009	journal	April 1985
Dioxygen affinities of synthetic cobalt Schiff base complexes Chen, Dian; Martell, A. E. Inorganic Chemistry, Vol. 26, Issue 7 https://doi.org/10.1021/ic00254a013	journal	April 1987
Redox reactions of cobalt-cyanide complexes. II. Reaction of pentacyanocobaltate(II) with p-benzoquinone. Properties of decacyano[.mu.-hydroquinnonato(2-)]dicobaltate(6-) Vlcek, Antonin A.; Hanzlik, Jiri Inorganic Chemistry, Vol. 6, Issue 11 https://doi.org/10.1021/ic50057a027	journal	November 1967
Preparation and oxidation of some quinone adducts of transition metal complexes Girgis, Amal Y.; Sohn, Y. S.; Balch, Alan L. Inorganic Chemistry, Vol. 14, Issue 10 https://doi.org/10.1021/ic50152a006	journal	October 1975
Magnetic exchange interactions in transition metal dimers. 11. Structural and magnetic characterization of [Ni2(tren)2(C6O4Cl2)](BPh4)2 and [Cu2(Me5dien)2(C6O4Cl2)](BPh4)2. Magnetic exchange interactions propagated by the dianions of 2,5-dihydroxy-1,4-benzoquinones Pierpont, Cortlandt G.; Francesconi, Lynn C.; Hendrickson, David N. Inorganic Chemistry, Vol. 16, Issue 9 https://doi.org/10.1021/ic50175a043	journal	September 1977
Magnetic exchange interactions in binuclear transition-metal complexes. 16. Binuclear ferric complexes from the reaction of iron(II)(salen) with p-quinones Kessel, Stephen L.; Hendrickson, David N. Inorganic Chemistry, Vol. 17, Issue 9 https://doi.org/10.1021/ic50187a053	journal	September 1978
Electrochemical investigation of a series of peroxo-bridged binuclear cobalt complexes Harris, Wesley R.; McLendon, George L.; Martell, Arthur E. Inorganic Chemistry, Vol. 19, Issue 1 https://doi.org/10.1021/ic50203a005	journal	January 1980
Iron(III), manganese(III), and cobalt(III) complexes with single chelating o-semiquinone ligands Kessel, Stephen L.; Emberson, R. M.; Debrunner, P. G. Inorganic Chemistry, Vol. 19, Issue 5 https://doi.org/10.1021/ic50207a012	journal	May 1980
Importance of Counterion Reactivity on the Deactivation of Co−Salen Catalysts in the Hydrolytic Kinetic Resolution of Epichlorohydrin Jain, Surbhi; Zheng, Xiaolai; Jones, Christopher W. Inorganic Chemistry, Vol. 46, Issue 21 https://doi.org/10.1021/ic700782f	journal	October 2007
Mechanistic studies on the cobalt(II) Schiff base catalyzed oxidation of olefins by O2 Hamilton, Dorothy E.; Drago, Russell S.; Zombeck, Alan Journal of the American Chemical Society, Vol. 109, Issue 2 https://doi.org/10.1021/ja00236a014	journal	January 1987
Novel cobalt(II)-catalyzed oxidative cleavage of a carbon-carbon double bond Drago, R. S.; Corden, B. B.; Barnes, C. W. Journal of the American Chemical Society, Vol. 108, Issue 9 https://doi.org/10.1021/ja00269a057	journal	April 1986
Mixed-valence semiquinone-catecholate-iron complexes Lynch, Michael W.; Valentine, Mark; Hendrickson, David N. Journal of the American Chemical Society, Vol. 104, Issue 25 https://doi.org/10.1021/ja00389a016	journal	December 1982
Activation of molecular oxygen. Kinetic studies of the oxidation of hindered phenols with cobalt-dioxygen complexes Zombeck, Alan; Drago, Russell S.; Corden, Barry B. Journal of the American Chemical Society, Vol. 103, Issue 25 https://doi.org/10.1021/ja00415a027	journal	December 1981
Nature of the bound oxygen in a series of cobalt dioxygen adducts Tovrog, Benjamin S.; Kitko, David J.; Drago, Russell S. Journal of the American Chemical Society, Vol. 98, Issue 17 https://doi.org/10.1021/ja00433a016	journal	August 1976
Novel peroxycobalt(III) complexes derived from 4-aryl-2,6-di-tert-butylphenols. A model intermediate of dioxygenase reaction Nishinaga, A.; Nishizawa, K.; Tomita, H. Journal of the American Chemical Society, Vol. 99, Issue 4 https://doi.org/10.1021/ja00446a064	journal	February 1977
Oxidation and reduction of iron porphyrins and hemoproteins by quinones and hydroquinones Castro, C. E.; Hathaway, G. M.; Havlin, R. Journal of the American Chemical Society, Vol. 99, Issue 24 https://doi.org/10.1021/ja00466a042	journal	November 1977
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
Voltammetry of Quinones in Unbuffered Aqueous Solution: Reassessing the Roles of Proton Transfer and Hydrogen Bonding in the Aqueous Electrochemistry of Quinones Quan, May; Sanchez, Daniel; Wasylkiw, Mark F. Journal of the American Chemical Society, Vol. 129, Issue 42, p. 12847-12856 https://doi.org/10.1021/ja0743083	journal	October 2007
Hydrogen-Bonding Interactions between Water and the One- and Two-Electron-Reduced Forms of Vitamin K ₁ : Applying Quinone Electrochemistry To Determine the Moisture Content of Non-Aqueous Solvents Hui, Yanlan; Chng, Elaine Lay Khim; Chng, Cheryl Yi Lin Journal of the American Chemical Society, Vol. 131, Issue 4 https://doi.org/10.1021/ja8080428	journal	February 2009
Hydrogen-Bonding and Protonation Effects in Electrochemistry of Quinones in Aprotic Solvents Gupta, Neeraj; Linschitz, Henry Journal of the American Chemical Society, Vol. 119, Issue 27 https://doi.org/10.1021/ja970028j	journal	July 1997
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
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. Journal of the American Chemical Society, Vol. 138, Issue 49 https://doi.org/10.1021/jacs.6b05797	journal	November 2016
Cobalt-Schiff Base Complex Catalyzed Oxidation of Para-Substituted Phenolics. Preparation of Benzoquinones Bozell, Joseph J.; Hames, Bonnie R.; Dimmel, Donald R. The Journal of Organic Chemistry, Vol. 60, Issue 8 https://doi.org/10.1021/jo00113a020	journal	April 1995
Oxygenation of 2,6-di-tert-butylphenols bearing an electron-withdrawing group in the 4-position Nishinaga, Akira; Shimizu, Tadashi; Toyoda, Yasushi The Journal of Organic Chemistry, Vol. 47, Issue 12 https://doi.org/10.1021/jo00133a009	journal	June 1982
Factors controlling the reactivity of a ligninase model based on the association of potassium monopersulfate to manganese and iron porphyrin complexes Labat, Gilles; Meunier, Bernard The Journal of Organic Chemistry, Vol. 54, Issue 21 https://doi.org/10.1021/jo00282a011	journal	October 1989
Synthesis of Enantiomerically Pure Lignin Dimer Models for Catalytic Selectivity Studies Njiojob, Costyl N.; Rhinehart, Jennifer L.; Bozell, Joseph J. The Journal of Organic Chemistry, Vol. 80, Issue 3 https://doi.org/10.1021/jo502685k	journal	January 2015
The Unusual Reaction of Semiquinone Radicals with Molecular Oxygen Valgimigli, Luca; Amorati, Riccardo; Fumo, Maria Grazia The Journal of Organic Chemistry, Vol. 73, Issue 5 https://doi.org/10.1021/jo7024543	journal	March 2008
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
Reaction of Superoxide Radical with Quinone Molecules Samoilova, Rimma I.; Crofts, Antony R.; Dikanov, Sergei A. The Journal of Physical Chemistry A, Vol. 115, Issue 42 https://doi.org/10.1021/jp204891n	journal	October 2011
The Structure and Function of Quinones in Biological Solar Energy Transduction: A Cyclic Voltammetry, EPR, and Hyperfine Sub-Level Correlation (HYSCORE) Spectroscopy Study of Model Naphthoquinones Coates, Christopher S.; Ziegler, Jessica; Manz, Katherine The Journal of Physical Chemistry B, Vol. 117, Issue 24 https://doi.org/10.1021/jp401024p	journal	June 2013
Characterizing Anharmonic Vibrational Modes of Quinones with Two-Dimensional Infrared Spectroscopy Cyran, Jenée D.; Nite, Jacob M.; Krummel, Amber T. The Journal of Physical Chemistry B, Vol. 119, Issue 29 https://doi.org/10.1021/jp506900n	journal	September 2014
Efficient Cobalt-Catalyzed Oxidative Conversion of Lignin Models to Benzoquinones Biannic, Berenger; Bozell, Joseph J. Organic Letters, Vol. 15, Issue 11 https://doi.org/10.1021/ol401065r	journal	May 2013
Inhibition of Cytochrome P450 Enzymes by Quinones and Anthraquinones Sridhar, Jayalakshmi; Liu, Jiawang; Foroozesh, Maryam Chemical Research in Toxicology, Vol. 25, Issue 2 https://doi.org/10.1021/tx2004163	journal	January 2012
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
π-Bonded quinonoid transition-metal complexes Reingold, Jeffrey A.; Uk Son, Seung; Bok Kim, Sang Dalton Trans., Issue 20 https://doi.org/10.1039/B602678H	journal	January 2006
Steric effects in the design of Co-Schiff base complexes for the catalytic oxidation of lignin models to para-benzoquinones Biannic, Berenger; Bozell, Joseph J.; Elder, Thomas Green Chem., Vol. 16, Issue 7 https://doi.org/10.1039/C4GC00709C	journal	January 2014
Transition-metal catalyzed valorization of lignin: the key to a sustainable carbon-neutral future Kärkäs, Markus D.; Matsuura, Bryan S.; Monos, Timothy M. Organic & Biomolecular Chemistry, Vol. 14, Issue 6 https://doi.org/10.1039/C5OB02212F	journal	January 2016
Quinone and its derivatives for energy harvesting and storage materials Son, Eun Jin; Kim, Jae Hong; Kim, Kayoung Journal of Materials Chemistry A, Vol. 4, Issue 29 https://doi.org/10.1039/C6TA03123D	journal	January 2016
Oxidation of phenols by molecular oxygen catalysed by transition metal complexes. Comparison between the activity of various cobalt and manganese complexes and the role of peroxy intermediates Frostin-Rio, Maryvonne; Pujol, Danièle; Bied-Charreton, Claude J. Chem. Soc., Perkin Trans. 1, Issue 0 https://doi.org/10.1039/P19840001971	journal	January 1984
Spectromagnetic investigation of the active species in the oxidation of propenoidic phenols catalysed by [N,N′-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) * Bolzacchini, Ezio; Canevali, Carmen; Morazzoni, Franca Journal of the Chemical Society, Dalton Transactions, Issue 24 https://doi.org/10.1039/a705188c	journal	January 1997
Oxidation studies of phenols with cobalt(II) ion-modified silica in a liquid chromatographic reactor Deng, Zengqun; Dieckmann, Gunnar R.; Langer, Stanley H. Journal of the Chemical Society, Perkin Transactions 2, Issue 5 https://doi.org/10.1039/a801253i	journal	January 1998
Oxidative degradation of monomeric and dimeric phenylpropanoids: reactivity and mechanistic investigation Canevali, Carmen; Orlandi, Marco; Pardi, Luca Journal of the Chemical Society, Dalton Transactions, Issue 15 https://doi.org/10.1039/b203386k	journal	July 2002
The effect of axial ligand on the oxidation of syringyl alcohol by Co(salen) adducts Elder, Thomas; Bozell, Joseph J.; Cedeno, Diana Physical Chemistry Chemical Physics, Vol. 15, Issue 19 https://doi.org/10.1039/c3cp44404j	journal	January 2013
Quinone adducts of cobalt(II) and iron(II) complexes with a quadridentate Schiff's base Floriani, C.; Fachinetti, G.; Calderazzo, F. Journal of the Chemical Society, Dalton Transactions, Issue 7 https://doi.org/10.1039/dt9730000765	journal	January 1973
Regioselective formation of peroxyquinolatocobalt(III) complexes in the oxygenation of 2,6-di-t-butylphenols with cobalt(II) Schiff-base complexes Nishinaga, Akira; Tomita, Haruo; Nishizawa, Kanji Journal of the Chemical Society, Dalton Transactions, Issue 7 https://doi.org/10.1039/dt9810001504	journal	January 1981
X-Ray and electrochemical investigation on a series of cobalt(II) complexes with quinquedentate ligands and their reactivity towards dioxygen Zanello, Piero; Cini, Renzo; Cinquantini, Arnaldo Journal of the Chemical Society, Dalton Transactions, Issue 10 https://doi.org/10.1039/dt9830002159	journal	January 1983
Reactivity of semiquinone radicals and its relation to the biochemical role of superoxide Sutton, Harry C.; Sangster, David F. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 78, Issue 3 https://doi.org/10.1039/f19827800695	journal	January 1982
Oxygenation of 2,6-di-t-butylphenol catalysed by a new cobalt(II) complex [Co(babp)]: a salen analogue having higher catalytic activity, selectivity, and durability Yamada, Masaki; Araki, Koji; Shiraishi, Shinsaku Journal of the Chemical Society, Perkin Transactions 1, Issue 10 https://doi.org/10.1039/p19900002687	journal	January 1990
Oxidation of Lignin Model Compounds with Cobalt‐sulphosalen Catalyst in the Presence and Absence of Carbohydrate Model Compound Sippola, V.; Krause, O.; Vuorinen, T. Journal of Wood Chemistry and Technology, Vol. 24, Issue 4 https://doi.org/10.1081/WCT-200046246	journal	January 2004
Ubiquinone-10 as an Antioxidant Petillo, David; Hultin, Herbert O. Journal of Food Biochemistry, Vol. 32, Issue 2 https://doi.org/10.1111/j.1745-4514.2008.00151.x	journal	April 2008
Alkaline quinone flow battery Lin, K.; Chen, Q.; Gerhardt, M. R. Science, Vol. 349, Issue 6255, p. 1529-1532 https://doi.org/10.1126/science.aab3033	journal	September 2015
Reactions of superoxide ion with redox-active substances of physiological importance: Generation of semiquinone radicals from physiologically important quinones. Ozawa, Toshihiko; Hanaki, Akira CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 31, Issue 8 https://doi.org/10.1248/cpb.31.2535	journal	January 1983
Catalysis-a potential alternative to kraft pulping Rudie, Alan W.; Hart, Peter W. TAPPI Journal, Vol. 13, Issue 10 https://doi.org/10.32964/TJ13.10.13	journal	November 2014
Electrochemical Reduction of Quinones in Different Media: A Review Guin, Partha Sarathi; Das, Saurabh; Mandal, P. C. International Journal of Electrochemistry, Vol. 2011, Article No. 816202 https://doi.org/10.4061/2011/816202	journal	January 2011
The Electrochemical Reaction Mechanism and Applications of Quinones Kim, R. Soyoung; Chung, Taek Dong Bulletin of the Korean Chemical Society, Vol. 35, Issue 11 https://doi.org/10.5012/bkcs.2014.35.11.3143	journal	November 2014

Similar Records

Cobalt-Schiff base complex catalyzed oxidation of para-substituted phenolics. Preparation of benzoquinones

Journal Article · Fri Apr 21 04:00:00 UTC 1995 · Journal of Organic Chemistry · OSTI ID:471560

Bozell, J J; Hames, B R; Dimmel, D R

DT-diaphorase-catalyzed two-electron reduction of various p-benzoquinone- and 1,4-naphthoquinone epoxides

Journal Article · Fri Jan 01 04:00:00 UTC 1988 · Free Radical Biology and Medicine; (USA) · OSTI ID:5668484

Brunmark, A; Cadenas, E; Segura-Aguilar, J; +2 more

Genotoxicity of 1,4-benzoquinone and 1,4-naphthoquinone in relation to effects on glutathione and NAD(P)H levels in V79 cells

Journal Article · Sat Jul 01 04:00:00 UTC 1989 · Environmental Health Perspectives; (USA) · OSTI ID:6967846

Ludewig, G; Dogra, S; Glatt, H

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Deactivation of Co-Schiff base catalysts in the oxidation of para-substituted lignin models for the production of benzoquinones

Citation Formats

References (105)

Similar Records

Related Subjects