How solvent modulates hydroxyl radical reactivity in hydrogen atom abstractions

Journal of the American Chemical Society

Volumn 132, Issue 9, 2010, Pages 2907-2913

  Mitroka, Susan ^a   Zimmeck, Stephanie ^a   Troya, Diego ^a   Tanko, James M ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

APROTIC SOLVENTS; AQUEOUS SOLUTIONS; BIMOLECULAR RATE CONSTANTS; GASPHASE; HYDROGEN ABSTRACTION; HYDROGEN ATOM ABSTRACTION; HYDROGEN BOND ACCEPTORS; HYDROGEN BOND DONORS; HYDROGEN BONDINGS; HYDROXYL RADICALS; POLARIZED TRANSITION STATE; REACTIVE OXYGEN; TRANSITION STATE;

ABSTRACTING; ACETONITRILE; HYDROGEN BONDS; ORGANIC SOLVENTS; OXYGEN; RATE CONSTANTS;

HYDROGEN;

ACETONITRILE; ALCOHOL DERIVATIVE; BENZENE; ETHER DERIVATIVE; HYDROGEN; HYDROXYL RADICAL; ORGANIC COMPOUND; OXYGEN; SOLVENT; STILBENE; WATER;

ARTICLE; ATOM; CONTROLLED STUDY; ELECTRON; GAS; HYDROGEN BOND; HYPOTHESIS; PHOTOLYSIS; POLARIZATION; SOLVATION;

ACETONITRILES; DIFFUSION; HYDROGEN; HYDROGEN BONDING; HYDROXYL RADICAL; ORGANIC CHEMICALS; SOLVENTS; WATER;

EID: 77949351936     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja903856t     Document Type: Article

References (49)

1. Tanko, J. M.; Suleman, N. K. Solvent Effects in the Reactions of Neutral Free Radicals. In Energetics of Organic Free Radicals; Simões, J. A. M., Greenberg, A., Liebman, J., Eds.; Chapman & Hall: New York, 1996; pp 224-293.
2. Russell, G. A. J. Am. Chem. Soc. 1958, 80, 4987-4996.
3. Litwinienko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222-230.
4. Li, S.; Matthews, J.; Sinha, A. Science 2008, 319, 1657-1660.
5. Vöhringer-Martinez, E.; Hansmann, B.; Hernandez-Soto, H.; Francisco, J. S.; Troe, J.; Abel, B. Science 2007, 315, 497-501.
6. Xu, G.; Chance, M. R. Chem. Rev. 2007, 107 (8), 3514-3543.
7. Boivin, J.; Crépon, E.; Zard, S. Z. Tetrahedron Lett. 1990, 47, 68696872.
8. (a) Aveline, B. M.; Kochevar, I. E.; Redmond, R. W. J. Am. Chem. Soc. 1995, 117, 9699-9708.
9. (b) DeMatteo, M. P.; Poole, J. S.; Shi, X.; Sachdeva, R.; Hatcher, P. G.; Hadad, C. M.; Platz, M. S. J. Am. Chem. Soc. 2005, 127, 7094-7109.
10. (c) Poole, J. S.; Shi, X.; Hadad, C. M.; Platz, M. S. J. Phys. Chem. A. 2005, 109, 2547-2551.
11. Russell, G. A. Reactivity, Selectivity, and Polar Effects in Hydrogen Atom Transfer Reactions. In Free Radicals; Kochi, J. K., Ed.; John Wiley & Sons, Inc.: New York, 1973; Vol.I pp 275-331.
12. Walling, C. Free Radicals in Solution; John Wiley & Sons, Inc.: New York, 1957.
13. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25-35.
14. (a) Merga, G.; Rao, B. S. M.; Mohan, H.; Mittal, J. P. J. Phys. Chem. 1994, 98, 9158-9164.
15. (b) Anbar, M.; Meyerstein, D.; Neta, P. J. Phys. Chem. 1966, 70, 2660-2662.
16. Frisch, M. J. et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
17. Finn, M.; Friedline, R.; Suleman, N. K.; Wohl, C. J.; Tanko, J. M. J. Am. Chem. Soc. 2004, 126, 7578-7584.
18. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 93, 466-470.
19. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: Weinheim, 1990.
20. Rudakov, E. S.; Volkova, L. K.; Tret' yakov, V. P. React. Kinet. Catal. Lett. 1981, 16, 333-337.
21. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513-886.
22. Willson, R. L.; Greenstock, C. L.; Adams, G. E.; Wageman, R.; Dorfman, L. M. Int. J. Radìat. Phys. Chem. 1971, 211-220.
23. Adams, G. E.; Boag, J. W.; Michael, B. D. Trans. Faraday Soc. 1965, 61, 1417-1424.
24. Adams, G. E.; Boag, J. W.; Currant, J.; Michael, B. D. In Pulse Radiolysis; Ebert, M., Keene, J. P., Swallow, A. J., Baxendale, J. H., Eds.; Academic Press: New York, 1965; pp 131-143.
25. Motohashi, N.; Saito, Y. Chem. Pharm. Bull. 1993, 41, 1842-1845.
26. Park, H.-R.; Getoff, N., Z. Z. Naturforsch. A: Phys. Sci. 1992, 47A, 985-991.
27. Wolfenden, B. S.; Willson, R. L. J. Chem. Soc., Perkin Trans. 1982, 805-812.
28. Matheson, M. S.; Mamou, A.; Silverman, J.; Rabani, J. J. Phys. Chem. 1973, 77, 2420-2424.
29. Elliot, A. J.; McCraken, D. R. Radiat. Phys. Chem. 1989, 33, 69-74.
30. Buxton, G. V. Trans. Faraday Soc. 1970, 66, 1656-1660.
31. Baxendale, J. H.; Khan, A. A. Int. J. Radiat. Phys. Chem. 1969, 1, 11-24.
32. Neta, P.; Dorfman, L. M. Adv. Chem. Ser. 1968, 81, 222-230.
33. Heckel, E.; Henglein, A.; Beck, G. Ber. Bunsenges. Phys. Chem. 1966, 70, 149-154.
34. Matthews, R. W.; Sangster, D. F. J. Phys. Chem. 1965, 69, 19381946.
35. Elliot, A. J.; Simsons, A. S. Radiat. Phys. Chem. 1984, 24, 229-231.
36. Greenstock, C. L.; Ng, M.; Hunt, J. W. Adv. Chem. Ser. 1968, 81, 397-417.
37. Thomas, J. K. Trans. Faraday Soc. 1965, 61, 702-707.
38. Eibenberger, J. Vienna University, Vienna, Austria, 1980.
39. Karpel Vel Leitner, N.; Papailhou, A.-L.; Croue, J.-P.; Peyrot, J.; Dore, M. Ozone Sci. Eng. 1994, 16, 41-54.
40. Mezyk, S. P.; Cooper, W. J.; Bartels, D. M.; O'Shea, K. E.; Wu, T. J. Phys. Chem. A 2001, 105, 3521-3526.
41. Haag, W. R.; Yao, C. C. D. Environ. Sci. Technol. 1992, 26, 10051013.
42. Getoff, N. Radiat. Phys. Chem. 1991, 37, 673-680.
43. Emmi, S. S.; Beggiato, G.; Casalbore-Miceli, G.; Fuochi, P. G. J. Radioanal. Nucl. Chem., Lett. 1985, 93, 189-197.
44. Lal, M.; Mahal, H. S. Radiât. Phys. Chem. 1992, 40, 23-26.
45. Rezansoff, B. J.; McCallum, K. J.; Woods, R. J. Can. J. Chem. 1970, 48, 271-276.
46. Anbar, M.; Meyerstein, D.; Neta, P. J. Chem. Soc. B 1966, 742-747.
47. Chutny, B. Collect. Czech. Chem. Commun. 1966, 31, 358-361.
48. Bednar, J.; Teply, J. Collect. Czech. Chem. Commun. 1960, 25, 842851.
49. Adams, G. E.; Boag, J. W.; Michael, B. D. Trans. Faraday Soc. 1965, 61, 492-505.