β-phenyl quenching of triplet excited ketones: How critical is the geometry for deactivation?

Journal of Organic Chemistry

Volumn 71, Issue 12, 2006, Pages 4453-4459

  Samanta, Subhas ^a   Mishra, Brijesh Kumar ^a   Pace, Tamara C S ^b   Sathyamurthy, Narayanasami ^a   Bohne, Cornelia ^b   Moorthy, Jarugu Narasimha ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; PHOTOLYSIS; QUENCHING; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

DEACTIVATION; PHENYL QUENCHING; STAGGERED CONFORMERS; TRIPLET EXCITED KETONES;

KETONES;

BETA PHENYL GROUP; BETA PHENYL RING; CARBONYL DERIVATIVE; FUNCTIONAL GROUP; KETONE; PHENYL GROUP; UNCLASSIFIED DRUG;

ALPHA SUBSTITUTION; ARTICLE; CHEMICAL PHENOMENA; CHEMICAL REACTION; CONFORMATION; CRITICAL GEOMETRY; CYCLIZATION; DEACTIVATION; DIASTEREOISOMER; EXCITATION; FORCE; FORCE FIELD; GEOMETRY; LASER FLASH PHOTOLYSIS; LIFESPAN; NONPHOTOCHEMICAL QUENCHING; NORRISH TYPE II REACTION; PHOTOLYSIS; ROTATION; SUBSTITUTION REACTION; TRIPLET EXCITED STATE; YANG CYCLIZTION;

EID: 33744903640     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060200e     Document Type: Article

References (32)

1. (a) Whitten, D. G.; Punch, W. E. Mol. Photochem. 1970, 2, 77.
2. (b) Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; Haug, A.; Graber, D. R. Mol. Photochem. 1970, 2, 81.
3. (c) Stermitz, F. R.; Nicodem, D. E.; Muralidharan, V. P.; O'Connell, C. D. Mol. Photochem. 1970, 2, 87.
4. (a) Scaiano, J. C.; Perkins, M. J.; Sheppard, J. W.; Platz, M. S.; Barcus, R. L. J. Photochem. 1983, 21, 137.
5. (b) Wismontski-Knittel, T.; Kilp, T. J. Phys. Chem. 1984, 88, 110.
6. (c) Netto-Ferreira, J. C.; Leigh, W. J.; Scaiano, J. C. J. Am. Chem. Soc. 1985, 107, 2617.
7. Leigh, W. J.; Banisch, J. H.; Workentin, M. S. J. Chem. Soc., Chem. Commun. 1993, 988.
8. (a) Guttenplan, J. B.; Cohen, S. G. J. Am. Chem. Soc. 1972, 94, 4040.
9. (b) Schuster, D. I.; Weil, T. M.; Halpern, A. M. J. Am. Chem. Soc. 1972, 94, 8248.
10. (c) Wolf, M. W.; Brown, R. E.; Singer, L. A. J. Am. Chem. Soc. 1977, 99, 526.
11. (d) Wagner, P. J.; Lam, M. H. J. Am. Chem. Soc. 1980, 102, 4166.
12. (e) Wagner, P. J.; Truman, R. J.; Puchalski, A. E.; Wake, R. J. Am. Chem. Soc. 1986, 108, 7727.
13. Boch, R.; Bohne, C.; Netto-Ferreira, J. C.; Scaiano, J. C. Can. J. Chem. 1991, 69, 2053.
14. (a) Moorthy, J. N.; Patterson, W. S.; Bohne, C. J. Am. Chem. Soc. 1997, 119, 11904.
15. (b) Moorthy, J. N.; Monahan, S. L.; Sunoj, R. B.; Chandrasekhar, J.; Bohne, C. J. Am. Chem. Soc. 1999, 121, 3093.
16. (a) Boch, R.; Bohne, C.; Scaiano, J. C. J. Org. Chem. 1996, 61, 1423.
17. (b) Ng, D.; Yang, Z.; Garcia-Garibay, M. A. Tetrahedron Lett. 2001, 42, 9113.
18. (a) Moorthy, J. N.; Mal, P. Tetrahedron Lett. 2003, 44, 2493.
19. (b) Singhal, N.; Koner, A. L.; Mal, P.; Venugopalan, P.; Nau, W. M.; Moorthy, J. N. J. Am. Chem. Soc. 2005, 127, 14375.
20. (a) Turro, N. J. Modern Molecular Photochemistry; Benjamin/ Cummings Publishing Co.: Menlo Park, NJ, 1978; p 628.
21. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: Oxford, 1991; p 538.
22. Liao, Y.; Bohne, C. J. Phys. Chem. 1996, 100, 734.
23. Wagner, P. J.; Kemppainen, A. E.; Schott, H. N. J. Am. Chem. Soc. 1973, 95, 5604.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian Inc.: Pittsburgh, PA, 2003.
25. (a) Wagner, P. J.; Kemppainen, A. E.; Schott, H. N. J. Am. Chem. Soc. 1970, 92, 5280.
26. (b) Wagner, P. J.; Nakahira, T. J. Am. Chem. Soc. 1973, 95, 8474.
27. (a) Lewis, F. D.; Hillard, T. A. J. Am. Chem. Soc. 1970, 92, 6672.
28. (b) Lewis, F. D.; Hillard, T. A. J. Am. Chem. Soc. 1972, 94, 3852.
29. (a) Pischel, U.; Abad, S.; Domingo, L. R.; Boscá, F.; Miranda, M. A. Angew. Chem., Int. Ed. 2003, 42, 2531.
30. (b) Boscá, F.; Andreu, I.; Morera, M.; Samadi, A.; Miranda, M. A. Chem. Commun. 2003, 1592.
31. (c) Pérez-Prieto, J.; Lahoz, A.; Boscá, F.; Martínez-Mañez, R.; Miranda, M. A. J. Org. Chem. 2004, 69, 374.
32. Khanna, R. N.; Mukerjee, S. K.; Ramanathan, J. D.; Seshadri, T. R. Ind. J. Chem. 1965, 3, 160.