DFT study of trichloroethene reaction with permanganate in aqueous solution

Environmental Science and Technology

Volumn 45, Issue 7, 2011, Pages 3006-3011

  Adamczyk, Paweł ^a   Dybala Defratyka, Agnieszka ^a   Paneth, Piotr ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

MANGANESE; TRICHLOROETHYLENE;

ACTIVATION PARAMETER; AQUEOUS SOLUTIONS; DFT STUDY; EXPERIMENTAL DATA; ISOTOPIC FRACTIONATIONS; TRANSITION STATE; TRICHLOROETHENES;

ISOTOPES;

CARBON; OXYGEN; PERMANGANATE POTASSIUM; TRICHLOROETHYLENE;

ANION; AQUEOUS SOLUTION; CARBON ISOTOPE; CHEMICAL BONDING; EXPERIMENTAL STUDY; ISOTOPIC FRACTIONATION; TRICHLOROETHYLENE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; FRACTIONATION; MOLECULAR MECHANICS;

EID: 84961973415     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es103251u     Document Type: Article

References (94)

1. ATSDR (Agency for Toxic Substances and Disease Registry) 2007 CERCLA Priority List of Hazardous Substances, U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, Division of Toxicology and Environmental Medicine, Atlanta, GA, in cooperation with U.S. Environmental Protection Agency, http://www.atsdr.cdc.gov/cercla/07list.html (accessed January 15, 2008).
2. Yamazaki-Nishida, S.; Cervera-March, S.; Nagano, K.; Anderson, M. A.; Hori, K. An Experimental and Theoretical Study of the Reaction Mechanism of the Photoassisted Catalytic Degradation of Trichloroethylene in the Gas Phase J. Phys. Chem. 1995, 99, 15814-15821
3. Dyksen, J. E.; Hess, A. F. Alternatives for controlling organics in groundwater supplies J. Am. Water Works Assoc. 1982, 74, 394-404
4. NRC. Alternatives for Groundwater Cleanup; National Academy Press: Washington, DC, 1994.
5. Pankow, A.; Cherry, J. A. Dense chlorinated solvents and other DNAPLs in groundwater; Waterloo Press: Waterloo, Canada, 1996.
6. IARC. Trichloroethylene; International Agency for Research on Cancer: Ottawa, Canada, 1995.
7. Xu, F.; Papanayotou, I.; Putt, D. A.; Wang, J.; Lash, L. H. Role of mitochondrial dysfunction in cellular responses to S-(1,2-dichlorovinyl)-L- cysteine in primary cultures of human proximal tubular cells Biochem. Pharmacol. 2008, 76, 552-567
8. Goldberg, S. J.; Lebowitz, M. D.; Graver, E. J.; Hicks, S. An association of human congenital cardiac malformations and drinking water contaminants J. Am. Coll. Cardiol. 1990, 16, 155-164 (Pubitemid 20217058)
9. Dawson, B. V.; Johnson, P. D.; Goldberg, S. J.; Ulreich, J. B. Cardiac teratogenesis of halogenated hydrocarbon-contaminated drinking water J. Am. Coll. Cardiol. 1993, 21, 1466-1472 (Pubitemid 23138718)
10. Boyer, A. S.; Finch, W. T.; Runyan, R. B. Trichloroethylene inhibits development of embryonic heart valve precursors in vitro Toxicol. Sci. 2000, 53, 109-117 (Pubitemid 30043610)
11. Collier, J. M.; Selmin, O.; Johnson, P. D.; Runyan, R. B. Trichloroethylene effects on gene expression during cardiac development Birth Defects Res., Part A 2003, 67, 488-495 (Pubitemid 37238036)
12. Drake, V. J.; Koprowski, S. L.; Lough, J.; Hu, N.; Smith, S. M. Trichloroethylene exposure during cardiac valvuloseptal morphogenesis alters cushion formation and cardiac hemodynamics in the avian embryo Environ. Health Perspect. 2006, 114, 842-847 (Pubitemid 43871731)
13. International Agency for Research on Cancer; IARC); Vinyl chloride; IARC Monogr. Eval. Carcinog. Risks Hum., Suppl. 7, 1987, 373.
14. Whittaker, M.; Monroe, D.; Oh, D. J.; Anderson, S.; 2008, Trichloroethylene pathway map. University of Minnesota biocatalysis/ biodegradation database: http://umbbd.msi.umn.edu/tce/tce-map.html (accessed January 15, 2008).
15. Hara, J.; Ito, H.; Suto, K.; Inoue, C.; Chida, T. Kinetics of trichloroethene dechlorination with iron powder Water Res. 2005, 39, 1165-1173
16. Lim, D.-H.; Lastoskie, Ch. M. Density Functional Theory Studies on the Relative Reactivity of Chloroethenes on Zerovalent Iron Environ. Sci. Technol. 2009, 43, 5443-5448
17. Bylaska, E. J.; Dupuis, M.; Tratnyek, P. G. One-Electron-Transfer Reactions of Polychlorinated Ethylenes: Concerted and Stepwise Cleavages J. Phys. Chem. A 2008, 112, 3712-3721
18. Yan, Y. E.; Schwartz, F. W. Kinetics and Mechanisms for TCE Oxidation by Permanganate Environ. Sci. Technol. 2000, 34, 2535-2541 (Pubitemid 30408018)
19. Hironen, A.; Tuhkanen, T.; Kalliokoski, P. Formation of chlorinated acetic acids during UV/H2O2-oxidation of ground water contaminated with chlorinated ethylenes Chemosphere 1996, 32, 1091-1102
20. Li, K.; Stefan, M. I.; Crittenden, J. C. UV Photolysis of Trichloroethylene: Product Study and Kinetic Modeling Environ. Sci. Technol. 2004, 38, 6685-6693
21. Pham, T. H.; Kitsuneduka, M.; Hara, J.; Suto, K.; Inoue, C. Trichloroethylene Transformation by Natural Mineral Pyrite: The Deciding Role of Oxygen Environ. Sci. Technol. 2008, 42, 7470-7475
22. Pham, T. H.; Kitsuneduka, M.; Hara, J.; Suto, K.; Inoue, C. Trichloroethylene Transformation in Aerobic Pyrite Suspension: Pathways and Kinetic Modeling Environ. Sci. Technol. 2009, 43, 6744-6749
23. Waldemer, R. H.; Tratnyek, P. G.; Johnson, R. L.; Nurmi, J. T. Oxidation of Chlorinated Ethenes by Heat-Activated Persulfate: Kinetics and Products Environ. Sci. Technol. 2007, 41, 1010-1015 (Pubitemid 46208544)
24. Technical and Regulatory Guidance for In Situ Chemical Oxidation of Contaminated Soil and Groundwater, 2 nd ed.; Interstate Technology and Regulatory Council (ITRC): Technical/Regulatory Guideline, 2005.
25. Houk, K. N.; Strassner, T. Establishing the (3 + 2) mechanism for the permanganate oxidation of alkenes by theory and kinetic isotope effects J. Org. Chem. 1999, 64, 800-802 (Pubitemid 29098003)
26. Wiberg, K. B.; Wang, Y.-G.; Sklenak, S.; Deutsch, C.; Trucks, G. Permanganate Oxidation of Alkenes. Substituent and Solvent Effects. Difficulties with MP2 Calculations J. Am. Chem. Soc. 2006, 128, 11537-11544 (Pubitemid 44338844)
27. Huang, K.-Ch; Hoag, G. E.; Chheda, P.; Woody, B. A.; Dobbs, G. M. Kinetics and mechanism of oxidation of tetrachloroethylene with permanganate Chemosphere 2002, 46, 815-25 (Pubitemid 34145726)
28. Poulson, S. R.; Naraoka, H. Carbon Isotope Fractionation during Permanganate Oxidation of Chlorinated Ethylenes (cDCE, TCE, PCE) Environ. Sci. Technol. 2002, 36, 3270-3274 (Pubitemid 34847595)
29. Hunkeler, D.; Aravena, R.; Parker, B. L.; Cherry, J. A.; Diao, X. Monitoring Oxidation of Chlorinated Ethenes by Permanganate in Groundwater Using Stable Isotopes: Laboratory and Field Studies Environ. Sci. Technol. 2003, 37, 798-804 (Pubitemid 36236699)
30. Frisch, M. J.. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
31. Zhao, Y.; Truhlar, D. G.; MN-GFM: Minnesota Gaussian Functional Module, Version 3.0, University of Minnesota, Minneapolis, MN, 2007.
32. Jaguar, version 7.6, Schrödinger, LLC: New York, NY, 2007.
33. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
34. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
35. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Chem. Phys. 1994, 98, 11623-11627
36. Yanai, T.; Tew, D. P.; Handy, N. C. A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Chem. Phys. Lett. 2004, 393, 51-57
37. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. Adiabatic Connection for Kinetics J. Phys. Chem. A 2000, 104, 4811-4815
38. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Exchange-correlation functional with broad accuracy for metallic and nonmetallic compounds, kinetics, and noncovalent interactions J. Chem. Phys. 2005, 123, 161103-161106
39. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions J. Chem. Theory Comput. 2006, 2, 364-382
40. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry Acc. Chem. Res. 2008, 41, 157-167
41. Zhao, Y.; Truhlar, D. G. 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 Theor. Chem. Acc. 2008, 120, 215-241
42. Zhao, Y.; Truhlar, D. G. A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions J. Chem. Phys. 2006, 125, 194101-194119
43. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Exploring the Limit of Accuracy of the Global Hybrid Meta Density Functional for Main-Group Thermochemistry, Kinetics, and Noncovalent Interactions J. Chem. Theory Comput. 2008, 4, 1849-1868
44. Tawada, Y.; Tsuneda, T.; Yanagisawa, S.; Yanai, T.; Hirao, K. A long-range-corrected time-dependent density functional theory J. Chem. Phys. 2004, 120, 8425-8433
45. Vydrov, O. A.; Scuseria, G. E. Assessment of a long-range corrected hybrid functional J. Chem. Phys. 2006, 125, 234109-234118
46. Vydrov, O. A.; Heyd, J.; Krukau, A.; Scuseria, G. E. Importance of short-range versus long-range Hartree-Fock exchange for the performance of hybrid density functionals J. Chem. Phys. 2006, 125, 074106-074101
47. Vydrov, O. A.; Scuseria, G. E.; Perdew, J. P. Tests of functionals for systems with fractional electron number J. Chem. Phys. 2007, 126, 154109-154118
48. Iikura, H.; Tsuneda, T.; Yanai, T.; Hirao, K. A long-range correction scheme for generalized-gradient-approximation exchange functionals J. Chem. Phys. 2001, 115, 3540-3544 (Pubitemid 32795665)
49. Tao, J. M.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Climbing the Density Functional Ladder: Nonempirical Meta-Generalized Gradient Approximation Designed for Molecules and Solids Phys. Rev. Lett. 2003, 91, 146401-146404
50. Møller, C.; Plesset, M. S. Note on the approximation treatment for many-electron systems Phys. Rev. 1934, 46, 618-622
51. Grimme, S. Semiempirical hybrid density functional with perturbative second-order correlation J. Chem. Phys. 2006, 124, 34108-34123
52. Miertus, S.; Scrocco, E.; Tomasi Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects Chem. Phys. 1981, 55, 117-129
53. Barone, V.; Cossi, M.; Tomasi, J. A new definition of cavities for the computation of solvation free energies by the polarizable continuum model J. Chem. Phys. 1997, 107, 3210-3221 (Pubitemid 127568937)
54. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations J. Am. Chem. Soc. 1992, 114, 10024-10035
55. Tannor, D. J.; Marten, B.; Murphy, R. B.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Ringnalda, M. N.; Goddard, W. A., III; Honig, B. Accurate First Principles Calculation of Molecular Charge Distributions and Solvation Energies from Ab Initio Quantum Mechanics and Continuum Dielectric Theory J. Am. Chem. Soc. 1994, 116, 11875-11882
56. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. A New Model For Calculation of Solvation Free Energies: Correction of Self-Consistent Reaction Field Continuum Dielectric Theory for Short Range Hydrogen-Bonding Effects J. Phys. Chem. 1996, 100, 11775-11788 (Pubitemid 126788600)
57. Friedrichs, M.; Zhou, R. H.; Edinger, S. R.; Friesner, R. A. Poisson-Boltzmann Analytical Gradients for Molecular Modeling Calculations J. Phys. Chem. B 1999, 103, 3057-3061 (Pubitemid 129702437)
58. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions J. Phys. Chem. B 2009, 113, 6378-6396
59. Hariharan, P. C.; Pople, J. A. Influence of Polarization Functions on MO Hydrogenation Energies Theor. Chim. Acta 1973, 28, 213-222
60. Ditchfield, R.; Hehre, W. J.; Pople, J. A. Self-consistent molecular-orbital methods. IX. Extended Gaussian-type basis for molecular-orbital studies of organic molecules J. Chem. Phys. 1971, 54, 724-728
61. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements J. Chem. Phys. 1982, 77, 3654-3665
62. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v R. Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21 + G basis set for first-row elements, lithium to fluorine J. Comput. Chem. 1983, 4, 294-301
63. Frisch, M. J.; Pople, J. A.; Binkley, J. S. Self-consistent molecular orbital methods. 25. Supplementary functions for Gaussian basis sets J. Chem. Phys. 1984, 80, 3265-3269
64. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions J. Chem. Phys. 1980, 72, 650-654
65. McLean, A. D.; Chandler, G. S. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z = 11-18 J. Chem. Phys. 1980, 72, 5639-5648
66. Raghavachari, K.; Trucks, G. W. Highly correlated systems. Excitation energies of first row transition metals Sc-Cu J. Chem. Phys. 1989, 91, 1062-1065
67. F. Weigend, F.; Ahlrichs, R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Phys. Chem. Phys. 2005, 7, 3297-3305 (Pubitemid 41412231)
68. Dunning, T. H., Jr. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen J. Chem. Phys. 1989, 90, 1007-1023
69. Woon, D. E.; Dunning, T. H., Jr. Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon J. Chem. Phys. 1993, 98, 1358-1371
70. Peterson, K. A.; Woon, D. E.; Dunning, T. H., Jr. Benchmark calculations with correlated molecular wave functions. IV. The classical barrier height of the H + H2 → H2 + H reaction J. Chem. Phys. 1994, 100, 7410-7415
71. Wilson, A. K.; van Mourik, T.; Dunning, T. H., Jr. Gaussian basis sets for use in correlated molecular calculations. VI. Sextuple-zeta correlation-consistent sets for boron through neon J. Mol. Struct. (Theochem) 1996, 388, 339-349 (Pubitemid 126404458)
72. Balabanov, N. B.; Peterson, K. A. Systematically convergent basis sets for transition metals. I. All-electron correlation consistent basis sets for the 3d elements Sc-Zn J. Chem. Phys. 2005, 123, 064107-064121
73. Fukui, K. Formulation of the reaction coordinate J. Phys. Chem. 1970, 74, 4161-4163
74. Bigeleisen, J. Statistical mechanics of isotope systems with small quantum corrections. General considerations and the rule of the geometric mean J. Chem. Phys. 1955, 23, 2264-2267
75. Bigeleisen, J. The relative reaction velocities of isotopic molecules J. Chem. Phys. 1949, 17, 675-678
76. Anisimov, V.; Paneth, P. ISOEFF98. A program for studies of isotope effects using Hssian modifications J. Math. Chem. 1999, 26, 75-86
77. Koester, C. J.; Simonich, S. L.; Esser, B. K. Environmental Analysis Anal. Chem. 2003, 75, 2813-2829 (Pubitemid 36702414)
78. Elsner, M.; Zwank, L.; Hunkeler, D.; Schwarzenbach, R. P. A New Concept Linking Observable Stable Isotope Fractionation to Transformation Pathways of Organic Pollutants Environ. Sci. Technol. 2005, 39, 6896-6916
79. Dybala-Defratyka, A.; Szatkowski, L.; Kaminski, R.; Wujec, M.; Siwek, A.; Paneth, P. Kinetic Isotope Effects on Dehalogenations at an Aromatic Carbon Environ. Sci. Technol. 2008, 42, 7744-7750
80. Hofstetter, T. H.; Schwarzenbach, R. P.; Bernasconi, S. M. Assessing Transformation Processes of Organic Compounds Using Stable Isotope Fractionation Environ. Sci. Technol. 2008, 42, 7737-7743
81. Meyer, M. P.; DelMonte, A. J.; Singleton, D. A. Reinvestigation of the Isotope Effects for the Claisen and Aromatic Claisen Rearrangements: The Nature of the Claisen Transition States J. Am. Chem. Soc. 1999, 121, 10865-10874 (Pubitemid 129541217)
82. Scott, A. P.; Radom, L. Harmonic Vibrational Frequencies: An Evaluation of Hartree-Fock, Moller-Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors J. Phys. Chem. 1996, 100, 16502-16513 (Pubitemid 126787989)
83. Wigner, E. Crossing of potential thresholds in chemical reaction Z. Phys. Chem. B 1932, 19, 203-216
84. Huang, K.-C.; Hoag, G. E.; Chheda, P.; Woody, B. A.; Dobbs, G. M. Kinetics and mechanism of oxidation of tetrachloroethylene wit permanganate Chemosphere 2002, 46, 815-825 (Pubitemid 34145726)
85. Improta, R.; Barone, V.; Scalmani, G.; Frisch, M. J. A state-specific polarizable continuum model time dependent density functional theory method for excited state calculations in solution J. Chem. Phys. 2006, 125, 054103-054112
86. Wheeler, S. E.; Houk, K. N. Integration Grid Errors for Meta-GGA-Predicted Reaction Energies: Origin of Grid Errors for the M06 Suite of Functionals J. Chem. Theory Comput. 2010, 6, 395-404
87. Mladek, A.; Sponer, J. E.; Jurecka, P.; Banas, P.; Otyepka, M.; Svozil, D.; Sponer, J. Conformational Energies of DNA Sugar-Phosphate Backbone: Reference QM Calculations and a Comparison with Density Functional Theory and Molecular Mechanics. J. Chem. Theory Comput. 2010, ASAP.
88. Świderek, K.; Paneth, P. Modeling excitation properties of iridium complexes J. Phys. Org. Chem. 2009, 22, 845-856
89. Wiberg, K. A. Application of the Pople-Santry-Segal complete neglect of differential overlap method to the cyclopropyl-carbinyl and cyclobutyl cation and to bicyclobutane Tetrahedron 1968, 24, 1083-1096
90. Martin, F.; Zipse, H. Charge distribution in the water molecule-a comparison of methods J. Comput. Chem. 2005, 26, 97-105 (Pubitemid 40021626)
91. Sharpless, K. B.; Teranishi, A. Y.; Backvall, J. E. Chromyl chloride oxidations of olefins. Possible role of organometallic intermediates in the oxidations of olefins by oxo transition metal species J. Am. Chem. Soc. 1977, 99, 3120-3128
92. Rappe, A. K.; Goddard, W. A., III. Olefin metathesis-a mechanistic study of high-valent Group VI catalysts J. Am. Chem. Soc. 1982, 104, 448-456
93. Flener-Lovitt, C.; Woon, D. E.; Dunning, T. H., Jr.; Girolami, G. S. A DFT and ab Initio Benchmarking Study of Metal-Alkane Interactions and the Activation of Carbon-Hydrogen Bonds J. Phys. Chem. A 2010, 114, 1843-1851
94. Bento, A. P.; Sola, M.; Bickelhaupt, F. M. E2 and SN2 Reactions of X- + CH3CH2X (X = F, Cl); an ab Initio and DFT Benchmark Study J. Chem. Theory Comput. 2008, 4, 929-940