Enantioselective discrimination in the intramolecular quenching of an excited aromatic ketone by a ground-state phenol [2]

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11569-11570

  Miranda, Miguel A ^a   Lahoz, Agustin ^a   Martínez Máñez, Ramón ^a   Boscá, Francisco ^a   Castell, José V ^b   Pérez Prieto, Julia ^c  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b HOSPITAL UNIVERSITARIO LA FE   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; KETONE; PHENOL; SUPROFEN; TIAPROFENIC ACID;

CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; ELECTRON TRANSPORT; ENANTIOMER; HYDROGEN BOND; LETTER; PHOTOCHEMISTRY; PHOTOLYSIS; STEREOCHEMISTRY;

EID: 0033572726     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990823s     Document Type: Letter

References (14)

1. Inoue, Y. Chem. Rev. 1992, 92, 741-770. Rau, H. Chem. Rev. 1983, 83, 535-547.
2. Inoue, Y. Chem. Rev. 1992, 92, 741-770. Rau, H. Chem. Rev. 1983, 83, 535-547.
3. Fox, M. A.; Chanon, M. Photoinduced Electron Transfer; Elsevier Science Publishers: Amsterdan, 1988; Part A.
4. Leigh, W. J.; Lathioor, E. C.; Pierre, M. J. St. J. Am. Chem. Soc. 1996, 118, 12339-12348. Scaiano, J. C.; McGimpsey, W. G.; Leigh, W. J.; Jakobs, S. J. Am. Chem. Soc. 1987, 52, 4540-4544.
5. Leigh, W. J.; Lathioor, E. C.; Pierre, M. J. St. J. Am. Chem. Soc. 1996, 118, 12339-12348. Scaiano, J. C.; McGimpsey, W. G.; Leigh, W. J.; Jakobs, S. J. Am. Chem. Soc. 1987, 52, 4540-4544.
6. Arnold, D. R.; Birtwell, R. J. J. Am. Chem. Soc. 1973, 95, 4599-4606. Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 67, 420-425. Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 68, 633-639.
7. Arnold, D. R.; Birtwell, R. J. J. Am. Chem. Soc. 1973, 95, 4599- 4606. Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 67, 420-425. Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 68, 633-639.
8. Arnold, D. R.; Birtwell, R. J. J. Am. Chem. Soc. 1973, 95, 4599- 4606. Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 67, 420-425. Encinas, S.; Miranda, M. A.; Marconi, G.; Monti, S. Photochem. Photobiol. 1998, 68, 633-639.
9. Bosca, F.; Miranda, M. A. J. Photochem. Photobiol. B: Bìol. 1998, 43, 1 -26. Miranda, M. A.; Castell, J. V.; Sarabia, Z.; Hernandez, D.; Puertes, I.; Morera, I. M.; Gómez-Lechén, M. J. Toxicol. Vitro 1997, 11, 653-659. Miranda, M. A.; Castell, J. V.; Hernández, D.; Gómez-Lechón, M. J.; Bosca, F.; Morera, I. M.; Sarabia, Z. Chem. Res. Toxicol. 1998, 11, 172-177.
10. Bosca, F.; Miranda, M. A. J. Photochem. Photobiol. B: Bìol. 1998, 43, 1 -26. Miranda, M. A.; Castell, J. V.; Sarabia, Z.; Hernandez, D.; Puertes, I.; Morera, I. M.; Gómez-Lechén, M. J. Toxicol. Vitro 1997, 11, 653-659. Miranda, M. A.; Castell, J. V.; Hernández, D.; Gómez-Lechón, M. J.; Bosca, F.; Morera, I. M.; Sarabia, Z. Chem. Res. Toxicol. 1998, 11, 172-177.
11. Bosca, F.; Miranda, M. A. J. Photochem. Photobiol. B: Bìol. 1998, 43, 1 -26. Miranda, M. A.; Castell, J. V.; Sarabia, Z.; Hernandez, D.; Puertes, I.; Morera, I. M.; Gómez-Lechén, M. J. Toxicol. Vitro 1997, 11, 653-659. Miranda, M. A.; Castell, J. V.; Hernández, D.; Gómez-Lechón, M. J.; Bosca, F.; Morera, I. M.; Sarabia, Z. Chem. Res. Toxicol. 1998, 11, 172-177.
12. 2 = 0.137 (all data), and GOF = 0.89. Absolute structure parameter = 0.05(6).
13. 2 = 0.132 (all data), and GOF = 1.12. Absolute structure parameter = 0.02(11).
14. Structure minimization was carried out using Mechanics as provided in the CAChe System Version 3.1 (Oxford Molecular Ltd., 1997). The molecular geometries of the minimum energy conformations were obtained using optimization routine.