Iron-Mediated Oxidation of Methoxyhydroquinone under Dark Conditions: Kinetic and Mechanistic Insights

Yuan, Xiu; Davis, James A.; Nico, Peter S.

doi:10.1021/acs.est.5b03939

Iron-Mediated Oxidation of Methoxyhydroquinone under Dark Conditions: Kinetic and Mechanistic Insights

Journal Article · Tue Jan 19 23:00:00 EST 2016 · Environmental Science and Technology

DOI:https://doi.org/10.1021/acs.est.5b03939· OSTI ID:1471008

Yuan, Xiu ^[1]; Davis, James A. ^[1]; Nico, Peter S. ^[1]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Earth and Environmental Sciences

Despite the biogeochemical significance of the interactions between natural organic matter (NOM) and iron species, considerable uncertainty still remains as to the exact processes contributing to the rates and extents of complexation and redox reactions between these important and complex environmental components. Investigations on the reactivity of low-molecular-weight quinones, which are believed to be key redox active compounds within NOM, toward iron species, could provide considerable insight into the kinetics and mechanisms of reactions involving NOM and iron. Here in this study, the oxidation of 2-methoxyhydroquinone (MH₂Q) by ferric iron (Fe(III)) under dark conditions in the absence and presence of oxygen was investigated within a pH range of 4-6. Although Fe(III) was capable of stoichiometrically oxidizing MH₂Q under anaerobic conditions, catalytic oxidation of MH₂Q was observed in the presence of O₂ due to further cycling between oxygen, semiquinone radicals, and iron species. A detailed kinetic model was developed to describe the predominant mechanisms, which indicated that both the undissociated and monodissociated anions of MH₂Q were kinetically active species toward Fe(III) reduction, with the monodissociated anion being the key species accounting for the pH dependence of the oxidation. The generated radical intermediates, namely semiquinone and superoxide, are of great importance in reaction-chain propagation. In conclusion, the kinetic model may provide critical insight into the underlying mechanisms of the thermodynamic and kinetic characteristics of metal-organic interactions and assist in understanding and predicting the factors controlling iron and organic matter transformation and bioavailability in aquatic systems.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1471008

Journal Information:: Environmental Science and Technology, Journal Name: Environmental Science and Technology Journal Issue: 4 Vol. 50; ISSN 0013-936X

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (70)

Oxidation of Hydroquinone by Copper: Chemical Mechanism and Biological Effects Li, Y. B.; Trush, M. A. Archives of Biochemistry and Biophysics, Vol. 300, Issue 1 https://doi.org/10.1006/abbi.1993.1047	journal	January 1993
The Pecking Order of Free Radicals and Antioxidants: Lipid Peroxidation, α-Tocopherol, and Ascorbate Buettner, G. R. Archives of Biochemistry and Biophysics, Vol. 300, Issue 2 https://doi.org/10.1006/abbi.1993.1074	journal	February 1993
A Stable Nonfluorescent Derivative of Resorufin for the Fluorometric Determination of Trace Hydrogen Peroxide: Applications in Detecting the Activity of Phagocyte NADPH Oxidase and Other Oxidases Zhou, Mingjie; Diwu, Zhenjun; Panchuk-Voloshina, Nataliya Analytical Biochemistry, Vol. 253, Issue 2 https://doi.org/10.1006/abio.1997.2391	journal	November 1997
Reduction of Substituted p-Benzoquinones by FeII Near Neutral pH Uchimiya, Minori; Stone, Alan T. Aquatic Geochemistry, Vol. 16, Issue 1 https://doi.org/10.1007/s10498-009-9077-0	journal	November 2009
The kinetics and thermodynamics of the reduction of cytochrome c by substituted p-benzoquinols in solution Rich, Peter R.; Bendall, Derek S. Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 592, Issue 3 https://doi.org/10.1016/0005-2728(80)90095-X	journal	October 1980
Electron transfer reactions between quinols and quinones in aqueous and aprotic media Rich, Peter R. Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 637, Issue 1 https://doi.org/10.1016/0005-2728(81)90206-1	journal	August 1981
Free energy correlation of rate constants for electron transfer between organic systems in aqueous solutions Meisel, Dan Chemical Physics Letters, Vol. 34, Issue 2 https://doi.org/10.1016/0009-2614(75)85269-9	journal	July 1975
Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone Eyer, Peter Chemico-Biological Interactions, Vol. 80, Issue 2 https://doi.org/10.1016/0009-2797(91)90022-Y	journal	January 1991
ESR evidence for the generation of reactive oxygen species from the copper-mediated oxidation of the benzene metabolite, hydroquinone: role in DNA damage Li, Yunbo; Kuppusamy, Periannan; Zweier, Jay L. Chemico-Biological Interactions, Vol. 94, Issue 2 https://doi.org/10.1016/0009-2797(94)03326-4	journal	February 1995
A mechanism for the reduction of cytochromes by quinols in solution and its relevance to biological electron transfer reactions Rich, Peter R.; Bendall, Derek S. FEBS Letters, Vol. 105, Issue 2 https://doi.org/10.1016/0014-5793(79)80608-0	journal	September 1979
Intracellular quinone reduction in Sporotrichum pulverulentum by a NAD(P)H: Quinone oxidoreductase: Possible role in vanillic acid catabolism Buswell, J. A.; Hamp, S.; Eriksson, K. -E. FEBS Letters, Vol. 108, Issue 1 https://doi.org/10.1016/0014-5793(79)81216-8	journal	December 1979
An electron spin resonance study of the reduction of peroxides by anthracycline semiquinones Kalyanaraman, B.; Sealy, R.; Sinha, B. Biochimica et Biophysica Acta (BBA) - General Subjects, Vol. 799, Issue 3 https://doi.org/10.1016/0304-4165(84)90270-8	journal	June 1984
Chemistry of superoxide ion-radical (O2−) in seawater. I. (HOO) and uncatalyzed dismutation kinetics studied by pulse radiolysis Zafiriou, O. C. Marine Chemistry, Vol. 30 https://doi.org/10.1016/0304-4203(90)90060-P	journal	January 1990
Dual effects of superoxide dismutase on the autoxidation of 1,4-naphthohydroquinone Ishii, T. Free Radical Biology and Medicine, Vol. 8, Issue 1 https://doi.org/10.1016/0891-5849(90)90140-E	journal	January 1990
One-electron-transfer reactions in biochemical systems I. Kinetic analysis of the oxidation-reduction equilibrium between quinol-quinone and ferro-ferricytochrome c Yamazaki, Isao; Ohnishi, Toshiyuki Biochimica et Biophysica Acta (BBA) - Biophysics including Photosynthesis, Vol. 112, Issue 3 https://doi.org/10.1016/0926-6585(66)90249-4	journal	March 1966
Reduction of Mn-oxides by ferrous iron in a flow system: column experiment and reactive transport modeling Postma, D.; Appelo, C. A. J. Geochimica et Cosmochimica Acta, Vol. 64, Issue 7 https://doi.org/10.1016/S0016-7037(99)00356-7	journal	April 2000
Electrochemical reactions with protonations at equilibrium Laviron, E. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 146, Issue 1 https://doi.org/10.1016/S0022-0728(83)80110-7	journal	April 1983
Abiotic Fe(III) induced mineralization of phenolic substances Pracht, J.; Boenigk, J.; Isenbeck-Schröter, M. Chemosphere, Vol. 44, Issue 4 https://doi.org/10.1016/S0045-6535(00)00490-2	journal	August 2001
The roles of natural organic matter in chemical and microbial reduction of ferric iron Chen, J.; Gu, B.; Royer, R. The Science of The Total Environment, Vol. 307, Issue 1-3 https://doi.org/10.1016/S0048-9697(02)00538-7	journal	May 2003
Kinetic analysis and mechanistic aspects of autoxidation of catechins Mochizuki, Manabu; Yamazaki, Shin-ichi; Kano, Kenji Biochimica et Biophysica Acta (BBA) - General Subjects, Vol. 1569, Issue 1-3 https://doi.org/10.1016/S0304-4165(01)00230-6	journal	January 2002
Metal-independent production of hydroxyl radicals by halogenated quinones and hydrogen peroxide: an ESR spin trapping study Zhu, Ben-Zhan; Zhao, Hong-Tao; Kalyanaraman, Balaraman Free Radical Biology and Medicine, Vol. 32, Issue 5 https://doi.org/10.1016/S0891-5849(01)00824-3	journal	March 2002
Global Kinetic Explorer: A new computer program for dynamic simulation and fitting of kinetic data Johnson, Kenneth A.; Simpson, Zachary B.; Blom, Thomas Analytical Biochemistry, Vol. 387, Issue 1 https://doi.org/10.1016/j.ab.2008.12.024	journal	April 2009
Ligand dependence in the copper-catalyzed oxidation of hydroquinones Mandal, Subrata; Kazmi, Najam H.; Sayre, Lawrence M. Archives of Biochemistry and Biophysics, Vol. 435, Issue 1 https://doi.org/10.1016/j.abb.2004.11.025	journal	March 2005
Reversible redox chemistry of quinones: Impact on biogeochemical cycles Uchimiya, Minori; Stone, Alan T. Chemosphere, Vol. 77, Issue 4 https://doi.org/10.1016/j.chemosphere.2009.07.025	journal	October 2009
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
Kinetics and mechanism of auto- and copper-catalyzed oxidation of 1,4-naphthohydroquinone Yuan, Xiu; Miller, Christopher J.; Pham, A. Ninh Free Radical Biology and Medicine, Vol. 71 https://doi.org/10.1016/j.freeradbiomed.2014.03.021	journal	June 2014
Redox reactions between iron and quinones: Thermodynamic constraints Uchimiya, Minori; Stone, Alan T. Geochimica et Cosmochimica Acta, Vol. 70, Issue 6 https://doi.org/10.1016/j.gca.2005.11.020	journal	March 2006
Oxygenation of Fe(II) in natural waters revisited: Kinetic modeling approaches, rate constant estimation and the importance of various reaction pathways Pham, A. Ninh; Waite, T. David Geochimica et Cosmochimica Acta, Vol. 72, Issue 15 https://doi.org/10.1016/j.gca.2008.05.032	journal	August 2008
Ferrous iron oxidation under acidic conditions – The effect of ferric oxide surfaces Jones, Adele M.; Griffin, Phillipa J.; Collins, Richard N. Geochimica et Cosmochimica Acta, Vol. 145 https://doi.org/10.1016/j.gca.2014.09.020	journal	November 2014
Ferrous iron oxidation by molecular oxygen under acidic conditions: The effect of citrate, EDTA and fulvic acid Jones, Adele M.; Griffin, Philippa J.; Waite, T. David Geochimica et Cosmochimica Acta, Vol. 160 https://doi.org/10.1016/j.gca.2015.03.026	journal	July 2015
Mechanistic insights into iron redox transformations in the presence of natural organic matter: Impact of pH and light Garg, Shikha; Jiang, Chao; David Waite, T. Geochimica et Cosmochimica Acta, Vol. 165 https://doi.org/10.1016/j.gca.2015.05.010	journal	September 2015
Flow Injection Analysis of H ₂ O ₂ in Natural Waters Using Acridinium Ester Chemiluminescence: Method Development and Optimization Using a Kinetic Model King, D. Whitney; Cooper, William J.; Rusak, Steven A. Analytical Chemistry, Vol. 79, Issue 11 https://doi.org/10.1021/ac062228w	journal	April 2007
Hydroquinone-Mediated Redox Cycling of Iron and Concomitant Oxidation of Hydroquinone in Oxic Waters under Acidic Conditions: Comparison with Iron–Natural Organic Matter Interactions Jiang, Chao; Garg, Shikha; Waite, T. David Environmental Science & Technology, Vol. 49, Issue 24 https://doi.org/10.1021/acs.est.5b03189	journal	December 2015
Rates and Mechanism of Fe(II) Oxidation at Nanomolar Total Iron Concentrations King, D. Whitney.; Lounsbury, Heather A.; Millero, Frank J. Environmental Science & Technology, Vol. 29, Issue 3 https://doi.org/10.1021/es00003a033	journal	March 1995
Electrochemical Properties of Natural Organic Matter (NOM), Fractions of NOM, and Model Biogeochemical Electron Shuttles Nurmi, James T.; Tratnyek, Paul G. Environmental Science & Technology, Vol. 36, Issue 4 https://doi.org/10.1021/es0110731	journal	February 2002
Aqueous Oxidation of Substituted Dihydroxybenzenes by Substituted Benzoquinones Uchimiya, Minori; Stone, Alan T. Environmental Science & Technology, Vol. 40, Issue 11 https://doi.org/10.1021/es052578k	journal	June 2006
Nature and Abundance of Organic Radicals in Natural Organic Matter: Effect of pH and Irradiation Paul, Andrea; Stösser, Reinhard; Zehl, Andrea Environmental Science & Technology, Vol. 40, Issue 19 https://doi.org/10.1021/es060742d	journal	October 2006
Electrochemical Analysis of Proton and Electron Transfer Equilibria of the Reducible Moieties in Humic Acids Aeschbacher, Michael; Vergari, Daniele; Schwarzenbach, René P. Environmental Science & Technology, Vol. 45, Issue 19 https://doi.org/10.1021/es201981g	journal	October 2011
Effects of pH, Chloride, and Bicarbonate on Cu(I) Oxidation Kinetics at Circumneutral pH Yuan, Xiu; Pham, A. Ninh; Xing, Guowei Environmental Science & Technology, Vol. 46, Issue 3 https://doi.org/10.1021/es203394k	journal	January 2012
Antioxidant Properties of Humic Substances Aeschbacher, Michael; Graf, Cornelia; Schwarzenbach, René P. Environmental Science & Technology, Vol. 46, Issue 9 https://doi.org/10.1021/es300039h	journal	April 2012
Impact of Natural Organic Matter on H ₂ O ₂ -Mediated Oxidation of Fe(II) in Coastal Seawaters Miller, Christopher J.; Vincent Lee, Siu Man; Rose, Andrew L. Environmental Science & Technology, Vol. 46, Issue 20 https://doi.org/10.1021/es3022792	journal	September 2012
Mechanism and Kinetics of Dark Iron Redox Transformations in Previously Photolyzed Acidic Natural Organic Matter Solutions Garg, Shikha; Ito, Hiroaki; Rose, Andrew L. Environmental Science & Technology, Vol. 47, Issue 4 https://doi.org/10.1021/es3035889	journal	February 2013
Hydroxyl Radical Production by H ₂ O ₂ -Mediated Oxidation of Fe(II) Complexed by Suwannee River Fulvic Acid Under Circumneutral Freshwater Conditions Miller, Christopher J.; Rose, Andrew L.; Waite, T. David Environmental Science & Technology, Vol. 47, Issue 2 https://doi.org/10.1021/es303876h	journal	December 2012
Iron Redox Transformations in Continuously Photolyzed Acidic Solutions Containing Natural Organic Matter: Kinetic and Mechanistic Insights Garg, Shikha; Jiang, Chao; Miller, Christopher J. Environmental Science & Technology, Vol. 47, Issue 16 https://doi.org/10.1021/es401087q	journal	August 2013
Copper-Catalyzed Hydroquinone Oxidation and Associated Redox Cycling of Copper under Conditions Typical of Natural Saline Waters Yuan, Xiu; Pham, A. Ninh; Miller, Christopher J. Environmental Science & Technology, Vol. 47, Issue 15 https://doi.org/10.1021/es4014344	journal	July 2013
Dark Formation of Hydroxyl Radical in Arctic Soil and Surface Waters Page, Sarah E.; Kling, George W.; Sander, Michael Environmental Science & Technology, Vol. 47, Issue 22 https://doi.org/10.1021/es4033265	journal	October 2013
Geochemical Production of Reactive Oxygen Species From Biogeochemically Reduced Fe Murphy, Sarah A.; Solomon, Benson M.; Meng, Shengnan Environmental Science & Technology, Vol. 48, Issue 7 https://doi.org/10.1021/es4051764	journal	March 2014
Biogeochemical Redox Processes and their Impact on Contaminant Dynamics Borch, Thomas; Kretzschmar, Ruben; Kappler, Andreas Environmental Science & Technology, Vol. 44, Issue 1 https://doi.org/10.1021/es9026248	journal	January 2010
Novel Electrochemical Approach to Assess the Redox Properties of Humic Substances Aeschbacher, Michael; Sander, Michael; Schwarzenbach, René P. Environmental Science & Technology, Vol. 44, Issue 1 https://doi.org/10.1021/es902627p	journal	January 2010
Influence of Organic Ligands on Chromium(VI) Reduction by Iron(II) Buerge, Ignaz J.; Hug, Stephan J. Environmental Science & Technology, Vol. 32, Issue 14 https://doi.org/10.1021/es970932b	journal	July 1998
Quinone Moieties Act as Electron Acceptors in the Reduction of Humic Substances by Humics-Reducing Microorganisms Scott, Durelle T.; McKnight, Diane M.; Blunt-Harris, Elizabeth L. Environmental Science & Technology, Vol. 32, Issue 19 https://doi.org/10.1021/es980272q	journal	October 1998
Pulse radiolytic studies of the reaction of perhydroxyl/superoxide O2- with iron(II)/iron(III) ions. The reactivity of HO2/O2- with ferric ions and its implication on the occurrence of the Haber-Weiss reaction Rush, James D.; Bielski, Benon H. J. The Journal of Physical Chemistry, Vol. 89, Issue 23 https://doi.org/10.1021/j100269a035	journal	November 1985
One-electron transfer equilibriums and redox potentials of radicals studied by pulse radiolysis Meisel, Dan; Czapski, Gideon The Journal of Physical Chemistry, Vol. 79, Issue 15 https://doi.org/10.1021/j100582a004	journal	July 1975
Equilibria of Substituted Semiquinones at High pH Bishop, C. A.; Tong, L. K. J. Journal of the American Chemical Society, Vol. 87, Issue 3 https://doi.org/10.1021/ja01081a018	journal	February 1965
Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains Hong, Yeonsun; Sengupta, Sandip; Hur, Wooyoung Journal of Medicinal Chemistry, Vol. 58, Issue 9 https://doi.org/10.1021/jm501846y	journal	April 2015
Stimulated anoxic biodegradation of aromatic hydrocarbons using Fe(III) ligands Lovley, Derek R.; Woodward, Joan C.; Chapelle, Francis H. Nature, Vol. 370, Issue 6485 https://doi.org/10.1038/370128a0	journal	July 1994
Humic substances as electron acceptors for microbial respiration Lovley, Derek R.; Coates, John D.; Blunt-Harris, Elizabeth L. Nature, Vol. 382, Issue 6590 https://doi.org/10.1038/382445a0	journal	August 1996
The kinetics and thermodynamics of quinone–semiquinone–hydroquinone systems under physiological conditions Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf Journal of the Chemical Society, Perkin Transactions 2, Issue 4 https://doi.org/10.1039/a807650b	journal	January 1999
Kinetics of oxidation of hydroquinones by molecular oxygen. Effect of superoxide dismutase Roginsky, Vitaly; Barsukova, Tatyana Journal of the Chemical Society, Perkin Transactions 2, Issue 7 https://doi.org/10.1039/b000538j	journal	January 2000
Kinetics and equilibria in the system ferrous ion + ferric ion + hydro-quinone + quinone Baxendale, J. H.; Hardy, H. R.; Sutcliffe, L. H. Transactions of the Faraday Society, Vol. 47 https://doi.org/10.1039/tf9514700963	journal	January 1951
Kinetics and equilibria in solutions containing ferrous ion, ferric ion, and some substituted hydroquinones and quinones Baxendale, J. H.; Hardy, H. R. Transactions of the Faraday Society, Vol. 50 https://doi.org/10.1039/tf9545000808	journal	January 1954
Pulse radiolysis of benzoquinone and hydroquinone. Semiquinone formation by water elimination from trihydroxy-cyclohexadienyl radicals Adams, G. E.; Michael, B. D. Transactions of the Faraday Society, Vol. 63 https://doi.org/10.1039/tf9676301171	journal	January 1967
Superoxide Radical Reactions in Aqueous Solutions of Pyrogallol and N-propyl Gallate: The Involvement of Phenoxyl Radicals. A Pulse Radiolysis Study Deeble, David J.; Parsons, Barry J.; Phillips, Glyn O. International Journal of Radiation Biology, Vol. 54, Issue 2 https://doi.org/10.1080/09553008814551621	journal	January 1988
Advanced Oxidation Processes for Organic Contaminant Destruction Based on the Fenton Reaction and Related Chemistry Pignatello, Joseph J.; Oliveros, Esther; MacKay, Allison Critical Reviews in Environmental Science and Technology, Vol. 36, Issue 1 https://doi.org/10.1080/10643380500326564	journal	January 2006
DNA damage resulting from the oxidation of hydroquinone by copper: role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation Li, Yunbo; Trush, Michael A. Carcinogenesis, Vol. 14, Issue 7 https://doi.org/10.1093/carcin/14.7.1303	journal	January 1993
Methoxyhydroquinone, an Intermediate of Vanillate Catabolism by Polyporus dichrous Kirk, T. Kent; Lorenz, L. F. Applied Microbiology, Vol. 26, Issue 2 https://doi.org/10.1128/AEM.26.2.173-175.1973	journal	January 1973
Methoxyhydroquinone, an Intermediate of Vanillate Catabolism by Polyporus dichrous Kirk, T. Kent; Lorenz, L. F. Applied Microbiology, Vol. 26, Issue 2 https://doi.org/10.1128/am.26.2.173-175.1973	journal	August 1973
THE REDUCTION OF CYTOCHROME c BY HYDROQUINONE Williams, G. R. Canadian Journal of Biochemistry and Physiology, Vol. 41, Issue 1 https://doi.org/10.1139/o63-028	journal	January 1963
Reduction of crystalline iron(III) oxyhydroxides using hydroquinone: Influence of phase and particle size Anschutz, Amy J.; Penn, R. Lee Geochemical Transactions, Vol. 6, Issue 3 https://doi.org/10.1186/1467-4866-6-60	journal	September 2005
Scavenging Effects of Dihydric and Polydric Phenols on Superoxide Anion Radicals, Studied by Electron Spin Resonance Spectrometry. Kitagawa, Shuji; Fujisawa, Hiroko; Sakurai, Hiromu Chemical and Pharmaceutical Bulletin, Vol. 40, Issue 2 https://doi.org/10.1248/cpb.40.304	journal	January 1992

Cited By (4)

Electron Transfer between Electrically Conductive Minerals and Quinones Taran, Olga Frontiers in Chemistry, Vol. 5 https://doi.org/10.3389/fchem.2017.00049	journal	July 2017
Elimination of 4‐chlorophenol in aqueous solution by the Novel Pd/MIL‐101(Cr)‐Hydrogen‐Accelerated catalytic fenton system Liu, Xin; Fan, Jin‐Hong; Liu, Zhong‐Xing Applied Organometallic Chemistry, Vol. 33, Issue 11 https://doi.org/10.1002/aoc.5194	journal	August 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
The construction of accelerated catalytic Fenton reaction based on Pd/MIL-101(Cr) and H ₂ Liu, Xin; Gao, Shi-Qian; Fan, Jin-Hong New Journal of Chemistry, Vol. 43, Issue 21 https://doi.org/10.1039/c9nj00204a	journal	January 2019

Similar Records

Iron-mediated oxidation of methoxyhydroquinone at Rifle, Colorado

Dataset · Mon Dec 31 23:00:00 EST 2018 · OSTI ID:1508396

Iron dynamics: Transformation of Fe(II)/Fe(III) during injection of natural organic matter in a sandy aquifer

Journal Article · Sat May 01 00:00:00 EDT 1993 · Geochimica et Cosmochimica Acta; (United States) · OSTI ID:6114617

Effects of fulvic acid on Fe(II) oxidation by hydrogen peroxide

Journal Article · Sun Mar 31 23:00:00 EST 1996 · Environmental Science and Technology · OSTI ID:226680

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
54 ENVIRONMENTAL SCIENCES

Iron-Mediated Oxidation of Methoxyhydroquinone under Dark Conditions: Kinetic and Mechanistic Insights

Citation Formats

References (70)

Cited By (4)

Similar Records

Related Subjects