Time resolved spectroscopy of some aromatic N-oxide triplets, radical anions, and related radicals

Journal of Physical Chemistry A

Volumn 108, Issue 20, 2004, Pages 4385-4390

  Shi, Xiaofeng ^a   Platz, Matthew S ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY (DFT); ELECTRON TRANSFER (ET); LASER FLASH PHOTOLYSIS (LFP); TIME RESOLVED INFRARED SPECTROSCOPY (TRIR);

COMPUTATIONAL METHODS; ENTHALPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; INFRARED SPECTROSCOPY; LASER APPLICATIONS; MATHEMATICAL MODELS; ORGANIC SOLVENTS; PHOTOLYSIS; VIBRATION CONTROL;

AROMATIC COMPOUNDS;

EID: 2642584157     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp037708v     Document Type: Article

References (18)

1. (a) Brown, J. M. Br. J. Cancer 1993, 67, 1163.
2. (b) Brown, J. M.; Siim, B. G. Seminars Rad. Oncol. 1996, 6, 22.
3. (c) Brown, J. M.; Wang, L.-H. Anti-Cancer Drug Design 1998, 13, 529.
4. (d) Brown, J. M. Cancer Res. 1999, 59, 5863.
5. (a) Daniels, J. S.; Gates, K. S. J. Am. Chem. Soc. 1996, 118, 3380.
6. (b) Daniels, J. S.; Gates, K. S.; Tronche, C.; Greenberg, M. M. Chem. Res. Toxicol. 1998, 11, 1254.
7. Poole, J. S.; Hadad, C. M.; Platz, M. S.; Fredin, Z. P.; Pickard, L.; Guerrero, E. L.; Kessler, M.; Chowdhury, G.; Kotandeniya, D.; Gates, K. S. Photochem. Photobiol. 2002, 75, 339.
8. Kaneko, C.; Yamamoto, A.; Gomi, M. Heterocycles 1979, 12, 227.
9. Martin, C. B.; Tsao, M. -L.; Hadad, C. M.; Platz, M. S. J. Am. Chem. Soc. 2002, 124, 7226.
10. Martin, C. B.; Shi, X.; Tsao. M.-L.; Karweik, D.; Brooke, J.; Hadad, C. M.; Platz, M. S. J. Phys. Chem. B 2002, 106, 10263.
11. 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, J. V.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L; 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.
12. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
13. Ono, I.; Hata, N. Bull. Chem. Soc. Jpn. 1973, 46, 3658.
14. Binstead, R. A.; McGuire. M. E.; Dovletoglou, A.; Seok, W. K.; Roecker, L. E.; Meyer, T. J. J. Am. Chem. Soc. 1992, 114, 173.
15. Kasama, K.: Takematsu, A.; Yamamoto, S.; Arai. S. J. Phys. Chem. 1984, 88, 4918.
16. Seki, H.; Takematsu, A.; Arai, S. J. Phys. Chem. 1987, 91, 176.
17. Shida, T. Electronic Absorption Spectra of Radical Ions; Elsevier: Amsterdam, 1988.
18. The mechanism by which this product is formed is not known. DFT calculations predict that direct fragmentation of triplet 4-nitroquinoline N-oxide to 4-nitroquinoline and oxene is endothermic by 29.5 kcal/mol in acetonitrile.