Modeling the oxidation of ebselen and other organoselenium compounds using explicit solvent networks

Journal of Physical Chemistry A

Volumn 113, Issue 19, 2009, Pages 5780-5785

  Bayse, Craig A ^a   Antony, Sonia ^a  

^a OLD DOMINION UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; DIMETHYLSELENIDE; EBSELEN; EXPLICIT SOLVENTS; FULL MODEL; INITIAL GUESS; METHYL MERCAPTANS; MICROSOLVATION; MODEL SYSTEM; NUCLEOPHILICITY; ORGANOSELENIUM COMPOUNDS; PROTON EXCHANGE; PROTON TRANSFER REACTIONS; SUBSTANTIAL REDUCTION; TRANSITION-STATE;

CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; HYDROGEN; HYDROGEN PEROXIDE; HYDROGEN SULFIDE; OXIDATION; PROTONS; RATE CONSTANTS; SELENIUM; SELENIUM COMPOUNDS; SOLVENTS;

PROTON TRANSFER;

EBSELEN; ORGANOSELENIUM DERIVATIVE; PROTON; PYRROLE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; THERMODYNAMICS;

AZOLES; MODELS, MOLECULAR; ORGANOSELENIUM COMPOUNDS; OXIDATION-REDUCTION; PROTONS; SOLVENTS; THERMODYNAMICS;

EID: 66149133651     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp901880n     Document Type: Article

References (39)

1. (a) Ganther, H. E. Carcinogenesis 1999, 20, 1657.
2. (b) Nordberg, J.; Arner, E. S. J. Free Radical Biol. Med. 2000, 31, 1287.
3. (c) Selenium: Its Molecular Biology and Role in Human Health; Hatfield, D. L., Berry, M. J., Gladyshev, V. N., Eds.; Springer: New York, 2006.
4. (d) Kayanoki, Y.; Fujii, J.; Islam, K. N.; Suzuki, K.; Kawata, S.; Matsuzawa, Y.; Taniguchi, N. J. Biochem. 1996, 119, 817.
5. (e) Rayman, M. P. Lancet 2000, 356, 233.
6. (f) Ghose, A.; Fleming, J.; Harrison, P. R. BioFactors 2001, 14, 127.
7. (g) Tapiero, H.; Townsend, D. M.; Tew, K. D. Biomed. Pharmacother. 2003, 57, 134.
8. Gromer, S.; Eubel, J. K.; Lee, B. L.; Jacob, J. Cell. Mol. Life Sci. 2005, 62, 2414.
9. (a) Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347.
10. (b) Mugesh, G.; du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125.
11. Lippman, S. M.; Goodman, P. J.; Klein, E. A.; Parnes, H. L.; Thompson, I. M.; Kristal, A. R.; Santella, R. M.; Probstfield, J. L.; Moinpour, C. M.; Albanes, D.; Taylor, P. R.; Minasian, L. M.; Hoque, A.; Thomas, S. M.; Crowley, J. J.; Gaziano, J. M.; Stanford, J. L.; Cook, E. D.; Fleshner, N. E.; Lieber, M. M.; Walther, P. J.; Khuri, F. R.; Karp, D. D.; Schwartz, G. G.; Ford, L. G.; Coltman, C. A. J. Natl. Cancer Inst. 2005, 97, 94.
12. Lapchak, P. A.; Zivin, J. A. Stroke 2003, 34, 2013.
13. Walter, R.; Roy, J. J. Org. Chem. 1971, 36, 2561.
14. Arnault, I.; Auger, J. J. Chromatogr., A 2006, 1112, 23.
15. Ganther, H. E.; Lawrence, J. R. Tetrahedron 1997, 53, 12299.
16. Schewe, T. Gen. Pharmacol. 1995, 26, 1152.
17. Gettins, P.; Crews, B. C. J. Biol. Chem. 1991, 266, 4804.
18. Bayse, C. A.; Antony, S. Main Group Chem. 2007, 6, 185, and references therein.
19. Bayse, C. A. J. Phys. Chem. A 2007, 111, 9070.
20. Prabhakar, R.; Vreven, T.; Morokuma, K.; Musaev, D. G. Biochemistry 2005, 44, 11864.
21. Pearson, J. K.; Boyd, R. J. J. Phys. Chem A 2006, 110, 8979.
22. (a) Musaev, D. G.; Geletti, Y. V.; Hill, C. L.; Hirao, K. J. Am. Chem. Soc. 2003, 125, 3877.
23. (b) Musaev, D. G.; Hirao, K. J. Phys. Chem. A 2003, 107, 1563.
24. (c) Musaev, D. G.; Geletu, Y. V.; Hill, C. L. J. Phys. Chem. A 2003, 107, 5862.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; A1-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
26. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
27. Hurley, M. M.; Pacios, L. F.; Christiansen, P. A.; Ross, R. B.; Ermler, W. C. J. Chem. Phys. 1986, 84, 6840.
28. Dunning, T. H. J. Chem. Phys. 1971, 55, 716.
29. Dunning, T. H. J. Chem. Phys. 1970, 53, 2823.
30. Lundin, A.; Panas, I.; Ahlberg, E. J. Phys. Chem. A 2007, 111, 9080.
31. Tomasi, J.; Mennuci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
32. Ritchey, J. A.; Davis, B. M.; Pleban, P. A.; Bayse, C. A. Org. Biol. Chem. 2005, 3, 4337.
33. Bayse, C. A.; Allison, B. A. J. Mol. Model. 2007, 13, 47.
34. Bayse, C. A.; Baker, R. A.; Ortwine, K. N. Inorg. Chim Acta 2005, 358, 3849, and references therein.
35. Fischer, H.; Dereu, N. Bull. Soc. Chim. Belg. 1987, 96, 757.
36. Sarma, B. K.; Mugesh, G. Chem.-Eur. J. 2008, 14, 10603.
37. Morgenstern, R.; Cotgreave, I. A.; Engman, L. Chem. -Biol. Interact. 1992, 84, 77.
38. Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477.
39. Bhabak, K. P.; Mugesh, G. Chem.-Eur. J. 2007, 13, 4594.