Electron Transfer and Singlet Oxygen Mechanisms in the Photooxygenation of Dibutyl Sulfide and Thioanisole in MeCN Sensitized by N-Methylquinolinium Tetrafluoborate and 9,10-Dicyanoanthracene. The Probable Involvement of a Thiadioxirane Intermediate in Electron Transfer Photooxygenations

Journal of the American Chemical Society

Volumn 125, Issue 52, 2003, Pages 16444-16454

  Baciocchi, Enrico ^a   Del Giacco, Tiziana ^b   Elisei, Fausto ^b   Gerini, Maria Francesca ^a   Guerra, Maurizio ^c   Lapi, Andrea ^a   Liberali, Prisca ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; DIMERS; FLUORESCENCE; OXIDATION; PHOTOLYSIS; QUENCHING;

ELECTRON TRANSFER (ET);

OXYGEN;

9,10 DICYANOANTHRACENE; ACETONITRILE; ANISOLE DERIVATIVE; ANTHRACENE DERIVATIVE; BENZOQUINONE; DIBUTYL SULFIDE; ETHYLENE OXIDE DERIVATIVE; N METHYLQUINOLINIUM TETRAFLUOBORATE; OXYGEN RADICAL; QUINOLINE DERIVATIVE; SINGLET OXYGEN; SULFIDE; SULFOXIDE; THIADIOXIRANE; THIOANISOLE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; ELECTRON TRANSPORT; FLUORESCENCE; LASER; PHOTOLYSIS; PHOTOOXIDATION; QUANTUM YIELD; REACTION ANALYSIS; SULFOXIDATION;

EID: 0347694569     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037591o     Document Type: Article

References (58)

1. Tung, C.-H.; Guan, J.-Q. J. Am. Chem. Soc. 1998, 120, 11874-11879.
2. Bonesi, S. M.; Nella, M.; d'Alessandro, N.; Aloisi, G. G.; Vanossi, M.; Albini, A. J. Org. Chem. 1998, 63, 9946-9955.
3. Toutchkine, A.; Clennan, E. L. J. Org. Chem. 1999, 64, 5620-5625.
4. Bonesi, S. M.; Albini, A. J. Org. Chem. 2000, 65, 4532-4536.
5. Toutchkine, A.; Aebisher, D.; Clennan, E. L. J. Am. Chem. Soc. 2001, 123, 4966-4973.
6. Clennan, E. L.; Zhou, W.; Chan, J. J. Org. Chem. 2002, 67, 9368-9378.
7. Lacombe, S.; Cardy, H.; Simon, M.; Khoukh, A.; Soumillion, J. Ph.; Ayadim, M. Photochem. Photobiol. Sci. 2002, 1, 347-354.
8. Zen, J. M.; Liou, S. L.; Kumar, A. S.; Hsia, M. S. Angew. Chem., Int. Ed. 2003, 42, 577-579.
9. Liang, J. J.; Gu, C. L.; Kacher, M. L.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4717-4721.
10. Ishiguro, K.; Hayashi, M.; Sawaki, Y. J. Am. Chem. Soc. 1996, 118, 7265-7271.
11. Jensen, F.; Greer, A.; Clennan, E. L. J. Am. Chem. Soc. 1998, 120, 4439-4449 and references therein.
12. Clennan, E. L. Acc. Chem. Res. 2001, 34, 875-884.
13. Soggiu, N.; Cardy, H.; Habib Jiwan, J. L.; Leray, I.; Soumillion, J. Ph. ; Lacombe, S. J. Photochem. Photobiol. A: Chem. 1999, 124, 1-8 and references therein.
14. Eriksen, J.; Foote, C. S. J. Am. Chem. Soc. 1980, 102, 6083-6088.
15. Steichen, D. S.; Foote, C. S. J. Am. Chem. Soc. 1981, 103, 1855-1857.
16. Silverman, S. K.; Foote, C. S. J. Am. Chem. Soc. 1991, 113, 7672-7675.
17. Araki, Y.; Dobrowolski, D. C.; Goyne, T. E.; Hanson, D. C.; Jiang, Z. Q. ; Lee, K. J.; Foote, C. S J. Am. Chem. Soc. 1984, 106, 4570-4575.
18. Dockery, K. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P. J. Am. Chem. Soc. 1997, 119, 1876-1883.
19. Yoon, U. C.; Quillen, S. L.; Mariano, P. S.; Swanson, R.; Stavinoha, J. L.; Bay, E. J. Am. Chem. Soc. 1983, 105, 1204-1218.
20. Gassman, P. G.; Mullins, M. J. Tetrahedron Lett. 1980, 21, 2219-2222.
21. Goto, Y.; Matsui, T.; Ozaki, S.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 1999, 121, 9497-9502.
22. Chanon, M.; Eberson, L. In Photoinduced Electron Transfer; Fox. M. A., Chanon, M., Eds.; Elsevier: Amsterdam. 1988; Part A, p 470.
23. Eriksen, J.; Foote, C. S.; Parker, T. L. J. Am. Chem. Soc. 1977, 99, 6455-6456.
24. Cerniani, A.; Modena, G. Gazz. Chim. Ital. 1959, 89, 843-853.
25. Donovan, P. F.; Conley, D. A. J. Chem. Eng. Data 1966, 11, 614.
26. Romani, A.; Elisei, F.; Masetti, F.; Favaro, G. J. Chem. Soc., Faraday Trans. 1992, 88, 2147-2154.
27. Görner, H.; Elisei, F.; Aloisi, G. G. J. Chem. Soc., Faraday Trans. 1992, 88, 29-34.
28. Elisei, F.; Aloisi, G. G., Lattarini, C.; Latterini, L.; Dall'Acqua, F.; Guiotto, A. Photochem. Photobiol. 1996, 64, 67-74.
29. Boduszek, B.; Shine, H. J. J. Org. Chem. 1988, 53, 5142-5143.
30. 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.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
31. Krupenie, P. J. Phys. Chem. Ref. Data 1972, 1, 423-534.
32. McKee, M. L. J. Am. Chem. Soc. 1998, 120, 3963-3969.
33. Scott, P. A.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
34. Cossi, M.; Barone, V.; Cammi, R.; Tommasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
35. max value of 495 nm has been reported. Göbl, M.; Bonifacic, M.; Asmus, K.-D. J. Am. Chem. Soc. 1984, 106, 5984-5988.
36. Yokoi, H.; Hatta, A.; Ishiguro, K.; Sawaki Y. J. Am. Chem. Soc. 1998, 120, 12728-12733.
37. Wilkinson, F.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1995, 24, 663-1021.
38. +* is slightly higher than that (20.6 kcal/mol) reported in the literature. Abraham, W.; Glänzel, A.; Stösser, R.; Grummt, U. W.; Köppel, H. J. Photochem. Photobiol. 1990, 51, 359-370.
39. Schaap, A. P.; Lopez, L.; Gagnon, S. D. J. Am. Chem. Soc. 1983, 105, 663-664.
40. Fukuzumi, S.; Fujita, M.; Noura, S.; Ohkubo, K.; Suenobu, T. Araki, Y.; Ito, O. J. Phys. Chem. A 2001, 105, 1857-1868.
41. Actually, in some experiments with air-saturated solutions, i.e., with a smaller oxygen concentration, it was possible to detect a very fast component (lifetime about 150 ns) in the early portion of the decay of the absorption at 550 nm, attributable to reaction 5.
42. Sawyer, D. T.; Chiericato, G., Jr.; Angelis, C. T.; Nanni, E. J., Jr.; Tsuchiya, T. Anal. Chem. 1982, 54, 1720-1724.
43. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271.
44. PhSMe (0.01 M) showed to be unreactive after 10 min of irradiation in the presence of rose bengal (0.2 mM) at 400-600 nm.
45. Fox, M. A., Chanon, M., Eds. Photoinduced Electron Transfer; Elsevier: 1988; Part A, p 475.
46. Manring, L. E.; Kramer, M. K.; Foote, C. S. Tetrahedron Lett. 1984, 25, 2523-2526.
47. 2 (0.09 μmol).
48. Asmus, K.-D. In Sulfur Centered Intermediates in Chemistry and Biology; Chatgilialoglu, C. K.-D., Asmus, K.-D., Eds.; Plenum Press: New York, 1990: Nato Asi Series, pp 155-172.
49. Quenching is probably related to the formation of a CT complex that does not proceed further towards radical ion formation.
50. Manring, L. E.; Gu, C.-L.; Foote, C. S. J. Phys. Chem. 1983, 87, 40-44.
51. Gu, C.-L.; Foote, C. S.; Kacher, M. L. J. Am. Chem. Soc. 1981, 103, 5949-5951.
52. Sawaki, Y.; Ogata, Y. J. Am. Chem. Soc. 1981, 103, 5947-5948.
53. Akasaka, T.; Haranaka, M.; Ando, W. J. Am. Chem. Soc. 1991, 113, 9898-9900.
54. Ando, W.; Kabe, Y.; Kobayashi, S.; Takyu, C.; Yamagishi, A. J. Am. Chem. Soc. 1980, 102, 4526-4528.
55. 2.
56. Other high-accuracy energy methods based on the Complete Basis Set model cannot be utilized since dimethyl persulfoxide was computed to be unstable (see Computational Details).
57. 2O. Miller, B. L.; Williams, T. D.; Schöneich J. Am. Chem. Soc. 1996, 118, 11014-11025.
58. Shangguan, C.; McAllister, M. A. THEOCHEM 1998, 422, 123-132.