The energetics of the hydrogenolysis, dehydrohalogenation, and hydrolysis of 4,4′-Dichloro-diphenyl-trichloroethane from ab initio electronic structure theory

Journal of Physical Chemistry A

Volumn 108, Issue 27, 2004, Pages 5883-5893

  Bylaska, Eric J ^a   Dixon, David A ^a,d   Felmy, Andrew R ^a   Aprà, Edoardo ^a   Windus, Theresa L ^a   Zhan, Chang Guo ^b   Tratnyek, Paul G ^c  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^b University of Kentucky   (United States)

^c OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^d UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROHALOGENATION; GAS-PHASE ENTROPY; REACTION ENERGIES; STANDARD STATES;

DEHYDROGENATION; DISSOCIATION; ELECTRONIC STRUCTURE; ENTROPY; HYDROLYSIS; PH EFFECTS; SUBSTITUTION REACTIONS;

ETHANE;

EID: 3142700672     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0312316     Document Type: Article

References (74)

1. Eisenreich, S. J.; Willford, W. A.; Strachan, W. M. J. The Role of atompspheric deposition in organic contaminant cycling in the Great Lakes. In Intermediate Pollutant Transport: Modelling and Field Measurements; Allen, D., Ed.; Plenum: New York, 1989.
2. Carson, R. Silent Spring; Houghton Mifflin Co: New York, 2002.
3. Macalady, D. L.; Tratnyek, P. G.; Grundl, T. J. J. Contam. Hydrol. 1986, 1, 1.
4. Wolfe, N. L.; Zepp, R. G.; Paris, D. F.; Baughman, G. L.; Hollis, R. C. Environ. Sci. Technol. 1977, 11, 1077.
5. Bylaska, E. J.; Dixon, D. A.; Felmy, A. R. J. Phys. Chem. A 2000, 104, 610.
6. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry; John Wiley & Sons: New York, 1993.
7. Bylaska, E. J.; Dixon, D. A.; Felmy, A. R.; Tratnyek, P. G. J. Phys. Chem. A 2002, 106, 11581.
8. Arnold, W. A.; Wignet, P.; Cramer, C. J. Environ. Sci. Technol. 2002, 36, 3536.
9. Nonnenberg, C.; van der Donk, W. A.; Zipzse, H. Phys. Rev. A 2002, 106, 8708.
10. Patterson, E. V.; Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 2001, 123, 2025.
11. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
12. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
13. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622.
14. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
15. Bartlett, R. J. J. Phys. Chem. 1989, 93, 1697.
16. Bartlett, R. J.; Stanton, J. F. In Reviews of Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Ed.; VCH Publishers: New York, 1995; Chapter 2.
17. Kucharski, S. A.; R. J. Bartlett. J. Adv. Quantum Chem. 1986, 18, 281.
18. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986.
19. Dixon, D. A. J. Phys. Chem. 1988, 92, 86.
20. Klamt, A.; Schuurmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 1993, 799.
21. Straatsma, T. P.; Apra, E.; Windus, T. L.; Dupuis, M.; Bylaska, E. J.; de Jong, W.; Hirata, S.; Smith, D. M. A.; Hackler, M. T.; Pollack, L.; Harrison, R. J.; Nieplocha, J.; Tipparaju, V.; Krishnan, M.; Brown, E.; Cisneros, G.; Fann, G. I.; Fruchtl, H.; Garza, J.; Hirao, K.; Kendall, R.; Nichols, J. A.; Tsemekhman, K.; Valiev, M.; Wolinski, K.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsei, H.; Deegan, M.; Dyall, K.; Elwood, D.; Glendening, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nakajima, T.; Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; van Lenthe, J.; Wong, A.; Zhang, Z. NWChem, A Computational Chemistry Package far Parallel Computers, 4,5 ed.; Pacific Northwest National Laboratory: Richland, WA, 2003.
22. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864.
23. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
24. Kohn, W.; Sham, L. J. Phys. Rev. 1965, A140, 1133.
25. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
26. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
27. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
28. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
29. Adamo, C.; Barone, V. J. Chem. Phys. 1997, 110, 6158.
30. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
31. Peterson, K. A.; Kendall, R. A.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 99, 1930.
32. Peterson, K. A.; Kendall, R. A.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 99, 9790.
33. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358.
34. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1995, 103, 4572.
35. Feller, D.; Schuchardt, K. Basis sets were obtained from the Extensible Computational Chemistry Environment Basis Set Database, Version 9/12/01, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory which is part of the Pacific Northwest Laboratory, P.O. Box 999, Richland, WA 99352, and funded by the U.S. Department of Energy, 2001.
36. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.4; Gaussian, Inc.: Pittsburgh, PA, 1998.
38. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
39. Pierotti, R. A. J. Phys. Chem. 1965, 69, 281.
40. Huron, M. J.; P. Claverie. J. Phys. Chem. 1974, 78, 1853.
41. Floris, F. M.; Tomasi, J.; Pascual Ahuir, J. L. J. Comput. Chem. 1991, 12, 784.
42. Honig, B.; Sharp, K. A.; Yang, A. J. Phys. Chem. 1993, 97, 1101.
43. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
44. Sitkoff, D.; Sharp, K. A.; Honig, B. J. Phys. Chem. 1994, 98, 1978.
45. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161.
46. Eckert, F.; Klamt, A. AIChE J. 2002, 48, 369.
47. Ben-Naim, A.; Marcus, Y. J. J. Chem. Phys. 1984, 81, 2016.
48. Pedretti, A.; Vistoli, G. VEGA, standard ed., Release 1.5.092; Win9x/ME/NT/2000/XP ed., 2003.
49. Felmy, A. R. Chapter 18. In Soil Science Society of Americal Special Publication; 1995, 42, 377.
50. Pitzer, K. S. Acc. Chem. Res. 1977, 10, 371.
51. Pitzer, K. S. Theory: Ion interaction approach. In Activity coefficients in electrolyte solutions; Pytckowicz, R. M., Ed.; CRC Press: Boca Raton, FL, 1979; p 157.
52. Harvie, C. E.; Greenberg, J. P.; Weare, J. H. Geochim. Cosmochim. Acta 1987, 51, 1045.
53. Martell, A. E.; Smith, R. M. Crically Selected Stability Constants of Metals Complexes Database, Version 2.0; NIST Standard Reference Data Program: Gaithersburg, MD, 1995.
54. Hu, A. T.; Sinke, G. C.; Mintz, M. J. J. Chem. Thermodyn. 1972, 4, 239.
55. Chase, J., M. W. Phys. Chem. Ref. Data, Monograph No. 9 1998, 9, 1.
56. Devore, J. A.; O'Neal, H. E. J. Phys. Chem. 1969, 73, 2644.
57. McQuarrie, D. A. Statistical Mechanics, 1st ed.; Harper & Row: New York, 1973.
58. Herzberg, G. Molecular Spectra and Molecular Structure II. Infared and Roman Spectra of Polyatomic Molecules, 2nd ed.; D. Van Nostrand Company, Inc: New York, 1947.
59. Urey, H. G. J. Am. Chem. Soc. 1923, 45, 1445.
60. Tolman, R. C.; Badger, R. M. J. Am. Chem. Soc. 1923, 45, 2277.
61. East, A. L. L.; Radom, L. J. Chem. Phys. 1997, 106, 6655.
62. Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428. Pitzer, K. S. Quantum Chemistry; Prentice-Hall: New York, 1953.
63. Pitzer, K. S.; Gwinn, W. D. J. Chem. Phys. 1942, 10, 428. Pitzer, K. S. Quantum Chemistry; Prentice-Hall: New York, 1953.
64. McQuarrie, D. A. Quantum Chemistry; University Science Books: Sausalito, CA, 1983.
65. Mackay, D.; Shiu, W. Y. J. Phys. Chem. Ref. Data 1981, 10, 1175.
66. Brimblecombe, P. Air Composition & Chemistry; Cambridge University Press: Cambridge, 1986.
67. Mak, F. T.; Zele, S. R.; Cooper, W. J.; Kurucz, C. N.; Waite, T. D.; Nickelsen, M. G. Water Res. 1987, 31, 219.
68. Zepp, R. G.; Braun, A. M.; Hoigne, J.; Leenheer, J. A. Environ. Sci. Technol. 1987, 21, 485.
69. Getman, G. D.; Pittman, C. U., Jr. Solvated Electron Reductions: A Versatile Alternative for Waste Remediation. In Chemical Degradation Methods for Wastes and Pollutants: Environmental and Industrial Applications; Tarr, M. A., Ed.; Marcel Dekker: New York, 2003.
70. Wagman, D. D. J. Phys. Chem. Ref. Data 1982, 11, Suppl. 2.
71. Shiraishi, H.; Sunaryo, G. R.; Ishigure, K. J. Phys. Chem. 1994, 98, 5164.
72. Coe, J. V. Int. Rev. Phys. Chem. 2001, 20, 33.
73. Tissandier, M. D.; Cowen, K. A.; Feng, W. Y.; Gundlach, E.; Cohen, M. H.; Earhart, A. D.; Coe, J. V.; Tuttle, T. R., Jr. J. Phys. Chem. A 1998, 102, 7787.
74. Appendix: Experimental and high quality ab initio values.