Sulfate radical oxidation of aromatic contaminants: a detailed assessment of density functional theory and high-level quantum chemical methods

Pari, Sangavi; Wang, Inger A.; Liu, Haizhou; Wong, Bryan M.

doi:10.1039/C7EM00009J

Title: Sulfate radical oxidation of aromatic contaminants: a detailed assessment of density functional theory and high-level quantum chemical methods

Journal Article · Tue Feb 14 00:00:00 EST 2017 · Environmental Science: Processes & Impacts

DOI:https://doi.org/10.1039/C7EM00009J· OSTI ID:1483459

Pari, Sangavi ^[1]; Wang, Inger A. ^[1];

^[1];

^[2]

Univ. of California, Riverside, CA (United States). Department of Chemical & Environmental Engineering
Univ. of California, Riverside, CA (United States). Department of Chemical & Environmental Engineering and Materials Science & Engineering Program

We present that advanced oxidation processes that utilize highly oxidative radicals are widely used in water reuse treatment. In recent years, the application of sulfate radical (SO₄˙^-) as a promising oxidant for water treatment has gained increasing attention. To understand the efficiency of SO₄˙^- in the degradation of organic contaminants in wastewater effluent, it is important to be able to predict the reaction kinetics of various SO₄˙^--driven oxidation reactions. In this study, we utilize density functional theory (DFT) and high-level wavefunction-based methods (including computationally-intensive coupled cluster methods), to explore the activation energies of SO₄˙^--driven oxidation reactions on a series of benzene-derived contaminants. Additionally, these high-level calculations encompass a wide set of reactions including 110 forward/reverse reactions and 5 different computational methods in total. Based on the high-level coupled-cluster quantum calculations, we find that the popular M06-2X DFT functional is significantly more accurate for OH^- additions than for SO₄˙^- reactions. Most importantly, we highlight some of the limitations and deficiencies of other computational methods, and we recommend the use of high-level quantum calculations to spot-check environmental chemistry reactions that may lie outside the training set of the M06-2X functional, particularly for water oxidation reactions that involve SO₄˙^- and other inorganic species.

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Research Organization:: Univ. of California, Riverside, CA (United States)

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

Grant/Contract Number:: SC0016269

OSTI ID:: 1483459

Journal Information:: Environmental Science: Processes & Impacts, Vol. 19, Issue 3; ISSN 2050-7887

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 48 works

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References (64)

Synergetic effect of combination of AOP's (hydrodynamic cavitation and H2O2) on the degradation of neonicotinoid class of insecticide Raut-Jadhav, Sunita; Saharan, Virendra Kumar; Pinjari, Dipak Journal of Hazardous Materials, Vol. 261 https://doi.org/10.1016/j.jhazmat.2013.07.012	journal	October 2013
Removal of Pharmaceutical and Personal Care Products from Reverse Osmosis Retentate Using Advanced Oxidation Processes Abdelmelek, Sihem Ben; Greaves, John; Ishida, Kenneth P. Environmental Science & Technology, Vol. 45, Issue 8 https://doi.org/10.1021/es104287n	journal	April 2011
Quadratic configuration interaction. A general technique for determining electron correlation energies Pople, John A.; Head‐Gordon, Martin; Raghavachari, Krishnan The Journal of Chemical Physics, Vol. 87, Issue 10 https://doi.org/10.1063/1.453520	journal	November 1987
Kinetics and mechanisms of cylindrospermopsin destruction by sulfate radical-based advanced oxidation processes He, Xuexiang; de la Cruz, Armah A.; O'Shea, Kevin E. Water Research, Vol. 63 https://doi.org/10.1016/j.watres.2014.06.004	journal	October 2014
A direct MP2 gradient method Frisch, Michael J.; Head-Gordon, Martin; Pople, John A. Chemical Physics Letters, Vol. 166, Issue 3 https://doi.org/10.1016/0009-2614(90)80029-D	journal	February 1990
An efficient reformulation of the closed‐shell coupled cluster single and double excitation (CCSD) equations Scuseria, Gustavo E.; Janssen, Curtis L.; Schaefer, Henry F. The Journal of Chemical Physics, Vol. 89, Issue 12 https://doi.org/10.1063/1.455269	journal	December 1988
Remediation of a winery wastewater combining aerobic biological oxidation and electrochemical advanced oxidation processes Moreira, Francisca C.; Boaventura, Rui A. R.; Brillas, Enric Water Research, Vol. 75 https://doi.org/10.1016/j.watres.2015.02.029	journal	May 2015
Electron-transfer processes: peroxydisulfate, a useful and versatile reagent in organic chemistry Minisci, Francesco; Citterio, Attilio; Giordano, Claudio Accounts of Chemical Research, Vol. 16, Issue 1 https://doi.org/10.1021/ar00085a005	journal	January 1983
Changes in precipitation with climate change Trenberth, Ke Climate Research, Vol. 47, Issue 1 https://doi.org/10.3354/cr00953	journal	March 2011
Impact of the Ultraviolet Photolysis of Monochloramine on 1,4-Dioxane Removal: New Insights into Potable Water Reuse Patton, Samuel; Li, Wei; Couch, Kylie D. Environmental Science & Technology Letters, Vol. 4, Issue 1 https://doi.org/10.1021/acs.estlett.6b00444	journal	December 2016
Electron correlation and solvation effects. I. Basic formulation and preliminary attempt to include the electron correlation in the quantum mechanical polarizable continuum model so as to study solvation phenomena del Valle, F. J. Olivares; Tomasi, J. Chemical Physics, Vol. 150, Issue 2 https://doi.org/10.1016/0301-0104(91)80124-Z	journal	February 1991
Polarizabilities of π-Conjugated Chains Revisited: Improved Results from Broken-Symmetry Range-Separated DFT and New CCSD(T) Benchmarks Oviedo, M. Belén; Ilawe, Niranjan V.; Wong, Bryan M. Journal of Chemical Theory and Computation, Vol. 12, Issue 8 https://doi.org/10.1021/acs.jctc.6b00360	journal	July 2016
Analytical MBPT(4) gradients Trucks, Gary W.; Watts, John D.; Salter, E. A. Chemical Physics Letters, Vol. 153, Issue 6 https://doi.org/10.1016/0009-2614(88)85248-5	journal	December 1988
Electron correlation and solvation effects. II. The description of the vibrational properties of a water molecule in a dielectric given by the application of the polarizable continuum model with inclusion of correlation effects Aguilar, M. A.; del Valle, F. J. Olivares; Tomasi, J. Chemical Physics, Vol. 150, Issue 2 https://doi.org/10.1016/0301-0104(91)80125-2	journal	February 1991
Degradation of Reactive Red 120 dye using hydrodynamic cavitation Saharan, Virendra Kumar; Badve, Mandar P.; Pandit, Aniruddha B. Chemical Engineering Journal, Vol. 178 https://doi.org/10.1016/j.cej.2011.10.018	journal	December 2011
A full coupled‐cluster singles and doubles model: The inclusion of disconnected triples Purvis, George D.; Bartlett, Rodney J. The Journal of Chemical Physics, Vol. 76, Issue 4 https://doi.org/10.1063/1.443164	journal	February 1982
Self-assembly of ordered water tetramers in an encapsulated [Br(H2O)12]− complex Saeed, Musabbir A.; Pramanik, Avijit; Wong, Bryan M. Chemical Communications, Vol. 48, Issue 69 https://doi.org/10.1039/c2cc30767g	journal	January 2012
Oxidation of Benzene by Persulfate in the Presence of Fe(III)- and Mn(IV)-Containing Oxides: Stoichiometric Efficiency and Transformation Products Liu, Haizhou; Bruton, Thomas A.; Li, Wei Environmental Science & Technology, Vol. 50, Issue 2 https://doi.org/10.1021/acs.est.5b04815	journal	December 2015
Comparison of Halide Impacts on the Efficiency of Contaminant Degradation by Sulfate and Hydroxyl Radical-Based Advanced Oxidation Processes (AOPs) Yang, Yi; Pignatello, Joseph J.; Ma, Jun Environmental Science & Technology, Vol. 48, Issue 4 https://doi.org/10.1021/es404118q	journal	February 2014
Degradation rates of benzotriazoles and benzothiazoles under UV-C irradiation and the advanced oxidation process UV/H2O2 Bahnmüller, Sabrina; Loi, Clara H.; Linge, Kathryn L. Water Research, Vol. 74 https://doi.org/10.1016/j.watres.2014.12.039	journal	May 2015
Linear Free Energy Relationships between Aqueous phase Hydroxyl Radical Reaction Rate Constants and Free Energy of Activation Minakata, Daisuke; Crittenden, John Environmental Science & Technology, Vol. 45, Issue 8 https://doi.org/10.1021/es1020313	journal	April 2011
Theory and implementation of the MBPT density matrix. An application to one-electron properties Trucks, Gary W.; Salter, E. A.; Sosa, Carlos Chemical Physics Letters, Vol. 147, Issue 4 https://doi.org/10.1016/0009-2614(88)80249-5	journal	June 1988
Fate of Endocrine-Disruptor, Pharmaceutical, and Personal Care Product Chemicals during Simulated Drinking Water Treatment Processes Westerhoff, Paul; Yoon, Yeomin; Snyder, Shane Environmental Science & Technology, Vol. 39, Issue 17 https://doi.org/10.1021/es0484799	journal	September 2005
Molecular Mechanism of NDMA Formation from N , N -Dimethylsulfamide During Ozonation: Quantum Chemical Insights into a Bromide-Catalyzed Pathway Trogolo, Daniela; Mishra, Brijesh Kumar; Heeb, Michèle B. Environmental Science & Technology, Vol. 49, Issue 7 https://doi.org/10.1021/es504407h	journal	March 2015
A new mixing of Hartree–Fock and local density‐functional theories Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 2 https://doi.org/10.1063/1.464304	journal	January 1993
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
Intermediates and Reaction Pathways from the Degradation of Microcystin-LR with Sulfate Radicals Antoniou, Maria G.; de la Cruz, Armah A.; Dionysiou, Dionysios D. Environmental Science & Technology, Vol. 44, Issue 19 https://doi.org/10.1021/es1000243	journal	October 2010
Density functional theory is straying from the path toward the exact functional Medvedev, Michael G.; Bushmarinov, Ivan S.; Sun, Jianwei Science, Vol. 355, Issue 6320 https://doi.org/10.1126/science.aah5975	journal	January 2017
QSARs for phenols and phenolates: oxidation potential as a predictor of reaction rate constants with photochemically produced oxidants Arnold, William A.; Oueis, Yan; O'Connor, Meghan Environmental Science: Processes & Impacts, Vol. 19, Issue 3 https://doi.org/10.1039/C6EM00580B	journal	January 2017
A computer-based prediction platform for the reaction of ozone with organic compounds in aqueous solution: kinetics and mechanisms Lee, Minju; Blum, Lorenz C.; Schmid, Emanuel Environ. Sci.: Processes Impacts, Vol. 19, Issue 3 https://doi.org/10.1039/C6EM00584E	journal	January 2017
Perfluorooctanoic Acid Degradation Using UV–Persulfate Process: Modeling of the Degradation and Chlorate Formation Qian, Yajie; Guo, Xin; Zhang, Yalei Environmental Science & Technology, Vol. 50, Issue 2 https://doi.org/10.1021/acs.est.5b03715	journal	December 2015
Detection of pharmaceutically active compounds in the rivers and tap water of the Madrid Region (Spain) and potential ecotoxicological risk Valcárcel, Y.; González Alonso, S.; Rodríguez-Gil, J. L. Chemosphere, Vol. 84, Issue 10 https://doi.org/10.1016/j.chemosphere.2011.05.014	journal	September 2011
Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/⋅O ⁻ in Aqueous Solution Buxton, George V.; Greenstock, Clive L.; Helman, W. Phillips Journal of Physical and Chemical Reference Data, Vol. 17, Issue 2 https://doi.org/10.1063/1.555805	journal	April 1988
Pharmaceuticals and Endocrine Disrupting Compounds in U.S. Drinking Water Benotti, Mark; Trenholm, Rebecca; Vanderford, Brett Environmental Science & Technology, Vol. 43, Issue 3, p. 597-603 https://doi.org/10.1021/es801845a	journal	December 2008
Occurrence and removal of pharmaceuticals and hormones through drinking water treatment Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc Water Research, Vol. 45, Issue 3 https://doi.org/10.1016/j.watres.2010.10.036	journal	January 2011
In Situ Chemical Oxidation of Contaminated Groundwater by Persulfate: Decomposition by Fe(III)- and Mn(IV)-Containing Oxides and Aquifer Materials Liu, Haizhou; Bruton, Thomas A.; Doyle, Fiona M. Environmental Science & Technology, Vol. 48, Issue 17 https://doi.org/10.1021/es502056d	journal	August 2014
A novel homogeneous Fenton-like system with Fe(III)–phosphotungstate for oxidation of organic compounds at neutral pH values Lee, Changha; Sedlak, David L. Journal of Molecular Catalysis A: Chemical, Vol. 311, Issue 1-2 https://doi.org/10.1016/j.molcata.2009.07.001	journal	September 2009
The free-radical chemistry of persulfate-based total organic carbon analyzers Peyton, Gary R. Marine Chemistry, Vol. 41, Issue 1-3 https://doi.org/10.1016/0304-4203(93)90108-Z	journal	January 1993
Degradation of Pharmaceuticals and Metabolite in Synthetic Human Urine by UV, UV/H ₂ O ₂ , and UV/PDS Zhang, Ruochun; Sun, Peizhe; Boyer, Treavor H. Environmental Science & Technology, Vol. 49, Issue 5 https://doi.org/10.1021/es504799n	journal	February 2015
Rate constants and mechanism of reaction of sulfate radical anion with aromatic compounds Neta, P.; Madhavan, V.; Zemel, Haya Journal of the American Chemical Society, Vol. 99, Issue 1 https://doi.org/10.1021/ja00443a030	journal	January 1977
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
Persistence of pharmaceutical compounds and other organic wastewater contaminants in a conventional drinking-water-treatment plant Stackelberg, Paul E.; Furlong, Edward T.; Meyer, Michael T. Science of The Total Environment, Vol. 329, Issue 1-3 https://doi.org/10.1016/j.scitotenv.2004.03.015	journal	August 2004
Standard Gibbs Free Energies of Reactions of Ozone with Free Radicals in Aqueous Solution: Quantum-Chemical Calculations Naumov, Sergej; von Sonntag, Clemens Environmental Science & Technology, Vol. 45, Issue 21 https://doi.org/10.1021/es2018658	journal	November 2011
Formation of bromate in sulfate radical based oxidation: Mechanistic aspects and suppression by dissolved organic matter Lutze, Holger V.; Bakkour, Rani; Kerlin, Nils Water Research, Vol. 53 https://doi.org/10.1016/j.watres.2014.01.001	journal	April 2014
Efficient visible light photo-Fenton-like degradation of organic pollutants using in situ surface-modified BiFeO3 as a catalyst An, Junjian; Zhu, Lihua; Zhang, Yingying Journal of Environmental Sciences, Vol. 25, Issue 6 https://doi.org/10.1016/S1001-0742(12)60172-7	journal	June 2013
Electronic Signatures of Large Amplitude Motions: Dipole Moments of Vibrationally Excited Local-Bend and Local-Stretch States of S ₀ Acetylene ^† Wong, Bryan M.; Steeves, Adam H.; Field, Robert W. The Journal of Physical Chemistry B, Vol. 110, Issue 38 https://doi.org/10.1021/jp061924x	journal	September 2006
MP2 energy evaluation by direct methods Head-Gordon, Martin; Pople, John A.; Frisch, Michael J. Chemical Physics Letters, Vol. 153, Issue 6 https://doi.org/10.1016/0009-2614(88)85250-3	journal	December 1988
Charge-Assisted Encapsulation of Two Chlorides by a Hexaprotonated Azamacrocycle Hossain, Md. Alamgir; Saeed, Musabbir A.; Fronczek, Frank R. Crystal Growth & Design, Vol. 10, Issue 4 https://doi.org/10.1021/cg100110f	journal	April 2010
Occurrence and fate of pharmaceutical products and by-products, from resource to drinking water Mompelat, S.; Le Bot, B.; Thomas, O. Environment International, Vol. 35, Issue 5 https://doi.org/10.1016/j.envint.2008.10.008	journal	July 2009
Development of a Group Contribution Method To Predict Aqueous Phase Hydroxyl Radical (HO•) Reaction Rate Constants Minakata, Daisuke; Li, Ke; Westerhoff, Paul Environmental Science & Technology, Vol. 43, Issue 16 https://doi.org/10.1021/es900956c	journal	August 2009
Electron correlation and solvation effects Del Valle, Francisco J. Olivares; Bonaccorsi, Rosanna; Cammi, Roberto Journal of Molecular Structure: THEOCHEM, Vol. 230 https://doi.org/10.1016/0166-1280(91)85186-B	journal	May 1991
Thermodynamic calculations for molecules with asymmetric internal rotors—application to 1,3-butadiene Wong, Bryan M.; Raman, Sumathy Journal of Computational Chemistry, Vol. 28, Issue 4 https://doi.org/10.1002/jcc.20536	journal	January 2007
A C ₃ Symmetric Nitrate Complex with a Thiophene-Based Tripodal Receptor Işıklan, Muhammet; Saeed, Musabbir A.; Pramanik, Avijit Crystal Growth & Design, Vol. 11, Issue 4 https://doi.org/10.1021/cg2001859	journal	April 2011
Assessment of the Performance of the M05−2X and M06−2X Exchange-Correlation Functionals for Noncovalent Interactions in Biomolecules Hohenstein, Edward G.; Chill, Samuel T.; Sherrill, C. David Journal of Chemical Theory and Computation, Vol. 4, Issue 12 https://doi.org/10.1021/ct800308k	journal	November 2008
Pharmaceuticals, hormones and bisphenol A in untreated source and finished drinking water in Ontario, Canada — Occurrence and treatment efficiency Kleywegt, Sonya; Pileggi, Vince; Yang, Paul Science of The Total Environment, Vol. 409, Issue 8 https://doi.org/10.1016/j.scitotenv.2011.01.010	journal	March 2011
The implementation of density functional theory within the polarizable continuum model for solvation Fortunelli, Alessandro; Tomasi, Jacopo Chemical Physics Letters, Vol. 231, Issue 1 https://doi.org/10.1016/0009-2614(94)01253-9	journal	December 1994
Contamination levels of human pharmaceutical compounds in French surface and drinking water Mompelat, S.; Thomas, O.; Le Bot, B. Journal of Environmental Monitoring, Vol. 13, Issue 10 https://doi.org/10.1039/c1em10335k	journal	January 2011
How Well Can New-Generation Density Functionals Describe the Energetics of Bond-Dissociation Reactions Producing Radicals? Zhao, Yan; Truhlar, Donald G. The Journal of Physical Chemistry A, Vol. 112, Issue 6 https://doi.org/10.1021/jp7109127	journal	February 2008
Note on an Approximation Treatment for Many-Electron Systems Møller, Chr.; Plesset, M. S. Physical Review, Vol. 46, Issue 7 https://doi.org/10.1103/PhysRev.46.618	journal	October 1934
Formation of an Amine-Water Cyclic Pentamer: A New Type of Water Cluster in a Polyazacryptand Saeed, Musabbir A.; Wong, Bryan M.; Fronczek, Frank R. Crystal Growth & Design, Vol. 10, Issue 4 https://doi.org/10.1021/cg100161a	journal	April 2010
Theoretical chemistry in solution. Some results and perspectives of the continuum methods and in particular of the polarizable continuum model Tomasi, Jacopo; Bonaccorsi, Rosanna; Cammi, Roberto Journal of Molecular Structure: THEOCHEM, Vol. 234 https://doi.org/10.1016/0166-1280(91)89026-W	journal	September 1991
Atomic and Molecular Electron Affinities: Photoelectron Experiments and Theoretical Computations Rienstra-Kiracofe, Jonathan C.; Tschumper, Gregory S.; Schaefer, Henry F. Chemical Reviews, Vol. 102, Issue 1 https://doi.org/10.1021/cr990044u	journal	January 2002
Taxonomic assessment of a toxic cyanobacteria shift in hypereutrophic Grand Lake St. Marys (Ohio, USA) Steffen, Morgan M.; Zhu, Zhi; McKay, Robert Michael L. Harmful Algae, Vol. 33 https://doi.org/10.1016/j.hal.2013.12.008	journal	March 2014
Reactivity and Role of SO ₅ ^•- Radical in Aqueous Medium Chain Oxidation of Sulfite to Sulfate and Atmospheric Sulfuric Acid Generation Das, Tomi Nath The Journal of Physical Chemistry A, Vol. 105, Issue 40 https://doi.org/10.1021/jp011255h	journal	October 2001

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