Ultrafast pump-probe studies of tert-butyl aroylperbenzoates and triplet energy interception by the O-O bond

Journal of Physical Chemistry A

Volumn 108, Issue 28, 2004, Pages 5926-5931

  Shah, Bipin K ^a   Gusev, Alex ^a   Rodgers, Michael A J ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION ENERGY; BOND ENERGY; ULTRAFAST PUMPS; WAVELENGTH;

COMPUTATIONAL GEOMETRY; DISSOCIATION; ENERGY DISSIPATION; ENERGY TRANSFER; MONOMERS; OPTIMIZATION; PHOTOLYSIS; PHOTOPOLYMERIZATION; PROBABILITY; SOLVENTS;

AROMATIC COMPOUNDS;

EID: 3242878145     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp049588c     Document Type: Article

References (49)

1. Contribution No. 523 from the Center for Photochemical Sciences.
2. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
3. El-Sayed, M. A. J. Chem. Phys. 1963, 38, 2834.
4. Shah, B. K.; Neckers, D. C. J. Am. Chem. Soc. 2004, 126, 1830.
5. Morlino, E. A.; Bohorquez, M. D.; Neckers, D. C.; Rodgers, M. A. J. J. Am. Chem. Soc. 1991, 113, 3599.
6. Shah B. K.; Rodgers, M. A. J.; Neckers, D. C. J. Phys. Chem. A, in press.
7. Wagner, P. J.; Waite, C. I. J. Phys. Chem. 1995, 99, 7388.
8. Wolf, M. W.; Brown, R. E.; Singer, L. A. J. Am. Chem. Soc. 1977, 99, 526.
9. Baum, E. J.; Pitts, J. N. J. Phys. Chem. 1966, 70, 2066.
10. Shah, B. K.; Neckers, D. C. J. Org. Chem. 2002, 67, 6117.
11. Thijs, L.; Gupta, S. N.; Neckers, D. C. J. Org. Chem. 1979, 44, 4123.
12. Shah, B. K.; Neckers, D. C. J. Org. Chem. 2003, 68, 8368.
13. (a) Gupta, S. N.; Thijs, L.; Neckers, D. C. J. Polym. Sci., Polym. Chem. Ed. 1981, 19, 855.
14. (b) Gupta, I.; Gupta, S. N.; Neckers, D. C. J. Polym. Sci., Polym. Chem. Ed. 1982, 20, 147.
15. (c) Abu-Abdoun, I.I.; Thijs, L.; Neckers, D. C. J. Polym. Sci., Polym. Chem. Ed. 1983, 21, 3129.
16. (d) Allen, N. S.; Hardy, S. J.; Jacobine, A. F.; Glaser, D. M.; Yang, B.; Wolf, D.; Catalina, F.; Navaratnam, S.; Parsons, B. J. J. Appl. Polym. Sci. 1991, 42, 1169.
17. (e) Wang, L.; Liu, X.; Li, Y. Macro-molecules 1998, 31, 3446.
18. Morse, P. M. Phys. Rev. 1929, 34, 57.
19. Sato, S. J. Chem. Phys. 1955, 23, 2465.
20. Johnston, H. S. Gas-Phase Reaction Rate Theory; Ronald Press: New York, 1966; Chapter 4.
21. (a) Greene, B. I.; Hochstrasser, R. M.; Weisman, R. B. J. Phys. Chem. 1979, 70,1247.
22. (b) Miyasaka, H.; Morita, K.; Kamada, K.; Mataga, N. Bull. Chem. Soc. Jpn. 1990, 63, 3385.
23. (c) Tamai, N.; Asahi, T.; Masuhara, H. Chem. Phys. Lett. 1992, 198, 413.
24. Ramseier, M.; Senn, P.; Wirz, J. J. Phys. Chem. A 2003, 107, 3305.
25. (a) Godfrey, T. S.; Hilpern, J. W.; Porter, G. Chem. Phys. Lett. 1967, 1, 490.
26. (b) Hochstrasser, R. M.; Lutz, H.; Scott, G. W. Chem. Phys. Lett. 1974, 24, 162.
27. McGarry, P. F.; Doubleday, C. E., Jr.; Wu, C.; Staab, H. A. Turro, N. J. J. Photochem. Photobiol., A 1994, 77, 109.
28. (a) Batley, M.; Kearns, D. R. Chem. Phys. Lett. 1968, 2, 423.
29. (b) Ohmori, N.; Suzuki, T.; Ito, M. J. Phys. Chem. 1988, 92, 1086.
30. El-Sayed, M. A.; Leyerle, R. J. Chem. Phys. 1975, 62, 1579.
31. Shah, B. K.; Neckers, D. C. Unpublished data. The reported value of the triplet energy of some of the BAPs (∼77 kcal/mol, ref 10) is incorrect.
32. (a) Kavarnos, G.; Cole, T.; Scribe, P.; Dalton, J. C.; Turro, N. J. J. Am. Chem. Soc. 1971, 93, 1032.
33. (b) Davidson, R. S.; Bonneau, R.; Joussot-Dubien, J.; Trethewey, K. R. Chem. Phys. Lett. 1980, 74, 318.
34. (c) Huppert, D.; Rand, S. D.; Reynolds, A. H.; Rentzepis, P. M. J. Phys. Chem. 1982, 77, 1214.
35. Basu, G.; Kunasik, M.; Anglos, D.; Secor, B.; Kuki, A. J. Am. Chem. Soc. 1990, 112, 9410.
36. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry; Marcel Dekker: New York, 1993; p 284.
37. As suggested by one of the reviewers, the modest polar solvent effect on the triplet decay rates may suggest some sort of ionic contribution to the decay and the process may involve electron transfer from O-O to the benzoyl moiety, Back electron transfer from the benzoyl to O-O may lead to cleavage of the latter.
38. De Schryver, F. C.; Boens, N. Adv. Photochem. 1977, 10, 359.
39. Zimmeiman, H. E.; McKelvey, R. D. J. Am. Chem. Soc. 1971, 93, 3638.
40. Lamola, A. A.; Leermakers, P. A.; Byers, G. W.; Hammond, G. S. J. Am. Chem. Soc. 1965, 87, 2322.
41. Schnepp, O.; Levy, M. J. Am. Chem. Soc. 1962, 84, 172.
42. Acyl peroxides show UV absorption starting at ∼280 nm (Hiatt, R. In Organic Peroxides; Swern, D., Ed.; John Wiley & Sons: New York, 1971; Vol. II, p 811). This indicates that the vertical electronic transition of these molecules would roughly require ∼102 kcal/mol of energy.
43. Eisinger, J.; Shulman, B. G. Science 1968, 161, 1311.
44. Lewis, G. N.; Calvin, M. Chem. Rev. 1939, 25, 273.
45. Scaiano, J. C.; Wubbels, G. G. J. Am. Chem. Soc. 1981, 103, 640.
46. Encinas, M. V.; Lissi, E. A. J. Photochem. 1982, 20, 153.
47. Hiatt, R. In Organic Peroxides; Swern, D., Ed.; John Wiley & Sons: New York, 1971; Vol. II, p 809.
48. Reference 16, p 210.
49. 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.9; Gaussian, Inc.: Pittsburgh, PA, 1998.