Time-resolved resonance Raman and density functional theory study of the deprotonation reaction of the triplet state of p-hydroxyacetophenone in water solution

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 8661-8675

  Zuo, Peng ^a   Ma, Chensheng ^a   Kwok, Wai Ming ^a   Chan, Wing Sum ^a   Phillips, David Lee ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; IONIZATION; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; NEGATIVE IONS; PROBABILITY DENSITY FUNCTION; RAMAN SPECTROSCOPY; SOLUTIONS;

DEPROTONATION/IONIZATION; P-HYDROXYACETOPHENONES; TIME-RESOLVED RESONANCE; ULTRAVIOLET PHOTOLYSIS;

KETONES;

4 HYDROXYACETOPHENONE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; MOLECULAR INTERACTION; PHOTOCHEMISTRY; RAMAN SPECTROMETRY; SPECTROSCOPY; TIME; VIBRATION;

ACETOPHENONES; ANIONS; KINETICS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PROTONS; SOLUTIONS; SPECTRUM ANALYSIS, RAMAN; TIME FACTORS; VIBRATION; WATER;

EID: 27444443332     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050761q     Document Type: Article

References (54)

1. (a) Givens, R. S.; Kueper, L. W. Chem. Rev. 1993, 93, 55-66 and references therein.
2. (b) Givens, R. S.; Athey, P. S.; Matuszewski, B.; Kueper, L. W., III; Xue, J. Y.; Fister, T. J. Am. Chem. Soc. 1993, 115, 6001-6012 and references therein.
3. (c) Gee, K. R.; Kueper, L. W., III; Barnes, J.; Dudley, G.; Givens, R. S. J. Org. Chem. 1996, 61, 1228-1233.
4. Givens, R. S.; Athey, P. S.; Kueper, L. W., III; Matuszewski, B.; Xue, J.-Y. J. Am. Chem. Soc. 1992, 114, 8708-8710.
5. (a) Gives, R. S.; Park, C.-H. Tetrahedron Lett. 1996, 37, 6259-6262.
6. (b) Park, C.-H.; Givens, R. S. J. Am. Chem. Soc. 1997, 119, 2453-2463.
7. (c) Givens, R. S.; Jung, A.; Park, C.-H.; Weber, J.; Bartlett, W. J. Am. Chem. Soc. 1997, 119, 8369-8370.
8. (d) Givens, R. S.; Weber, J. F. W.; Conrad, P. G., II; Orosz, G.; Donahue, S. L.; Thayer, S. A. J. Am. Chem. Soc. 2000, 122, 2687-2697 and references therein.
9. (e) Conrad, P. G., II; Givens, R. S.; Weber, J. F. W.; Kandler, K. Org. Lett. 2000, 2, 1545-1547.
10. (a) Conrad, P. G., II; Givens, R. S.; Hellrung, B.; Rajesh, C. S.; Ramseier, M.; Wirz, J. J. Am. Chem. Soc. 2000, 122, 9346-9347.
11. (b) Il'ichev, Y. V.; Schworer, M. A.; Wirz, J. J. Am. Chem. Soc. 2004, 126, 4581-4595.
12. (c) Rajesh, C. S.; Givens, R. S.; Wirz, J. J. Am. Chem. Soc. 2000, 122, 611-618.
13. (d) Hangarter, M.-A.; Hörmann, A.; Kamdzhilov, Y.; Wirz, J. Photochem. Photobiol. Sci. 2003, 2, 524-535.
14. (a) Banerjee, A.; Falvey, D. E. J. Am. Chem. Soc. 1998, 120, 2965-2966.
15. (b) Lee, K.; Falvey, D. E. J. Am. Chem. Soc. 2000, 122, 9361-9366.
16. (c) Banerjee, A.; Lee, K.; Yu, Q.; Fan, A. G.; Falvey, D. E. Tetrahedron Lett. 1998, 39, 4635-4638.
17. (d) Banerjee, A.; Falvey, D. E. J. Org. Chem. 1997, 62, 6245-6251.
18. (a) Zhang, K.; Corrie, J. E. T.; Munasinghe, V. R. N.; Wan, P. J. Am. Chem. Soc. 1999, 121, 5625-5632.
19. (b) Brousmiche, D. W.; Wan, P. J. Photochem. Photobiol., A 2000, 130, 113-118.
20. Namiki, S.; Arai, T.; Fujimori, K. J. Am. Chem. Soc. 1997, 119, 3840-3841.
21. Sheehan, J. C.; Umezawa, K. J. Org. Chem. 1973, 38, 3771-3774.
22. Pelliccioli, A. P.; Wirz, J. Photochem. Phobiol. Sci. 2002, 1, 441-458.
23. Falvey, D. E.; Sundarajan, C. Photochem. Phobiol. Sci. 2004, 3, 831-838.
24. Bochet, C. G. J. Chem. Soc., Perkin Trans, 1 2002, 2, 125-142.
25. Pillai, V. N. R. Synthesis, 1980, 1-26.
26. Zabadal, M.; Klan, P. Chem. Listy 2001, 95, 694-699.
27. Ma, C.; Kwok, W. M.; Chan, W. S.; Zuo, P.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Am. Chem., Soc. 2005, 127, 1463-1472.
28. (a) Ma, C.; Chan, W. S.; Kwok, W. M.; Zuo, P.; Phillips, D. L. J. Phys. Chem. B 2004, 108, 9264-9276.
29. (b) Ma, C.; Zuo, P.; Kwok, W. M.; Chan, W. S.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Org. Chem. 2004, 69, 6641-6657.
30. (a) Porter, G.; Suppan, P. Trans. Faraday Soc. 1965, 61, 1664-1673.
31. (b) Beckett, A.; Porter, G. Trans. Faraday Soc. 1963, 59, 2051-2057.
32. Chan, W. S.; Ma, C.; Kwok, W. M.; Phillips, D. L. J. Phys. Chem. A 2005, 109, 3454-3469.
33. (a) Li, Y.-L.; Leung, K. H.; Phillips, D. L. J. Phys. Chem. A 2001, 105, 10621-10625.
34. (b) Li, Y.-L.; Chen, D. M.; Wang, D.; Phillips, D. L. J. Org. Chem. 2002, 67, 4228-4235.
35. (c) Li, Y.-L.; Wang, D.; Phillips, D. L. J. Chem. Phys. 2002, 117, 7931-7941.
36. (d) Ong, S. Y.; Zhu, P.; Poon, Y. F.; Leung, K.-H.; Fang, W. H. Chem. Eur. J. 2002, 8, 2163-2171.
37. (e) Ong, S. Y.; Chan, P. Y.; Zhu, P.; Leung, K. H.; Phillips, D. L. J. Phys. Chem. A 2003, 107, 3858-3865.
38. (f) Chan, P. Y.; Kwok, W. M.; Lam, S. K.; Chiu, P.; Phillips, D. L. J. Am. Chem. Soc. 2005, 127, 8246-8247.
39. 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.; Baboul, A. G.; 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
40. (a) Kwok, W. M.; Ma, C.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M.; Umapathy, S. J. Phys. Chem. A 2001, 105, 984-990.
41. (b) Kwok, W. M.; Ma, C.; Parker, A. W.; Phillips, D.; Towrie, M.; Matousek, P.; Phillips, D. L. J. Chem. Phys. 2000, 113, 7471-7478.
42. (c) Ma, C.; Kwok, W. M.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. J. Photochem. Photobiol., A 2001, 142, 177-185.
43. (d) Kwok, W. M.; Gould, I.; Ma, C.; Puranik, M.; Umapathy, S.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Phys. Chem. Chem. Phys. 2001, 3, 2424-2432.
44. Kiritani, M.; Yoshii, T.; Hirota, N. J. Phys. Chem. 1994, 98, 11265-11268.
45. (a) Lim, E. C.; Li, Y. H.; Li, R. J. Chem. Phys. 1970, 53, 2443-2448.
46. (b) Li, R.; Lim, E. C. J. Chem. Phys. 1972, 57, 605-612.
47. (c) Li, Y. H.; Lim, E. C. Chem. Phys. Lett. 1970, 7, 15-18.
48. Kwok, W. M.; George, M. W.; Grills, D. C.; Ma, C.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Angew. Chem., Int. Ed. 2003, 42, 1826-1830.
49. Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 7747-7753.
50. Kagiya, T.; Sumida, Y.; Inoue, T. Bull. Chem. Soc. Jpn. 1968, 41, 767-773.
51. Allerhand, A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1963, 85, 371-380.
52. Fuson, N.; Josien, M.; Shelton, E. M. J. Am. Chem. Soc. 1954, 76, 2526-2533.
53. Woutersen, S.; Mu, Y.; Stock, G.; Hamm, P. Chem. Phys. 2001, 266, 137-147.
54. Schade, B.; Hagen, V.; Schmidt, R.; Herbrich, R.; Krause, E.; Eckardt, T.; Bendig, J. J. Org. Chem. 1999, 64, 9109-9117.