Fluorescent quenching of the 2-naphthoxide Anion by aliphatic and aromatic halides. Mechanism and consequences of electron transfer reactions

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2362-2368

  Argüello, Juan E ^a   Peñéñory, Alicia B ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSFER REACTIONS;

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CHEMICAL BONDS; ETHERS; NEGATIVE IONS; PHOTOCHEMICAL REACTIONS; QUENCHING; SUBSTITUTION REACTIONS;

FLUORESCENCE;

2 NAPTHOXIDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; DIMETHYL SULFOXIDE; HALIDE; UNCLASSIFIED DRUG;

ANION TRANSPORT; ARTICLE; COMPLEX FORMATION; COUPLING FACTOR; DRUG ISOLATION; ELECTRON TRANSPORT; FLUORESCENCE; PHOTOSTIMULATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0345382565     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026518y     Document Type: Article

References (43)

1. (a) Fox, M. A.; Chanon, M., Eds. Photoinduced Electron Transfer; Elsevier: The Hague, 1988.
2. (b) The complete volumes of the following recent journals: Chem. Rev. 1992, 92. J. Photochem. Photobiol A. Chem. 1994, 82.
3. (b) The complete volumes of the following recent journals: Chem. Rev. 1992, 92. J. Photochem. Photobiol A. Chem. 1994, 82.
4. (a) Rossi, R. A.; Pierini, A. B.; Palacios, S. M. Advances in Free Radical Chemistry; Tanner, D. D., Ed.; Jai Press: London, UK, 1990; pp 193-252.
5. (b) Lund, H.; Daasbjerg, K.; Lund, T.; Pedersen, S. U. Acc. Chem. Res. 1995, 28, 313-319.
6. (c) Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. In The Chemistry of the Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, UK, 1995; Suppl. D2, Chapter 24, pp 1395-1485.
7. (d) Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. Chem. Rev. 2003, 103, 71-167.
8. Pierini, A. B.; Baumgartner, M. T.; Rossi, R. A. J. Org. Chem. 1991, 56, 580-586.
9. Kornblum, N.; Cheng, L.; Davies, T. M.; Earl, G. W.; Holy, N. L.; Kerber, R. C.; Kestner, M. M.; Manthey, J. W.; Musser, M. T.; Pinnick, H. W.; Snow, D. H.; Stuchal, F. W.; Swiger, R. T. J. Org. Chem. 1987, 52, 196-204.
10. Kornblum, N.; Davies, M. T.; Earl, G. W.; Greene, G. S.; Holy, N. L.; Kerber, R. C.; Manthey, J. W.; Musser, M. T.; Snow, D. H. J. Am. Chem. Soc. 1967, 89, 5714-5715.
11. Pierini, A. B.; Borosky, G. L.; Baumgartner, M. T. Int. J. Quantum Chem. 1992, 44, 759-772.
12. (a) Soumillion, J. Ph.; Vandereecken, P.; Van Der Auweraer, M.; De Schryver, F. C.; Schanck, A. J. Am. Chem. Soc. 1989, 111, 2217-2225,
13. (b) Legros, B.; Vandereecken, P.; Soumillion, J. Ph. J. Phys. Chem. 1991, 95, 4752-4761.
14. Murov, S. L.; Carmichael, I.; Hung, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993.
15. Perkins, P. R.; Pincock, R. E. Tetrahedron Lett. 1975, 11, 943-946.
16. (a) Savéant, J. M. Adv. Phys. Org. Chem. 1990, 26, 1-130.
17. (b) Savéant, J. M. Adv. Electron-Transfer Chem. 1994, 4, 53-116.
18. (c) Savéant, J. M. Acc. Chem. Res. 1993, 26, 455-461.
19. (d) Lund, H.; Daasbjerg, K.; Lund, T.; Occhialini, D.; Pedersen, S. U. Acta Chem. Scand. 1997, 51, 135-144.
20. Pierini, A. B.; Duca, J. S., Jr.; Baumgartner, M. T. THEOCHEM 1994, 311, 343-352 and references therein.
21. (a) Savéant, J. M. J. Am. Chem. Soc., 1987, 109, 6788-6795.
22. (b) Savéant, J. M. J. Am. Chem. Soc. 1992, 114, 10595-10602.
23. Savéant, J.-M. Adv. Phys. Org. Chem. 2000, 35, 117-192.
24. (a) Antonello, S.; Maran, F. J. Am. Chem. Soc. 1997, 119, 12595-12600.
25. (b) Daasbjerg, K.; Jensen, H.; Benassi, R.; Taddei, F.; Antonello, S.; Gennaro, A.; Maran, F. J. Am. Chem. Soc. 1999, 121, 7150-7151.
26. Andrieux, C. P.; Robert, M.; Saeva, F. D.; Savéant, J. M. J. Am. Chem. Soc. 1994, 116, 7864-7871.
27. Andrieux, C. P.; Savéant, J. M.; Tardy, C. J. Am. Chem. Soc. 1997, 119, 11546-11547.
28. Pause, L.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 1999, 121, 7158-7159.
29. Vera, M. PhD Thesis, adviser Prof. Dra. Adriana B. Pierini, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, 2001.
30. (a) Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2000, 122, 514-517.
31. (b) Costentin, C.; Robert, M.; Savéant, J.-M. J. Phys. Chem. A 2000, 104, 7492-7501.
32. (a) Pause, L.; Robert, M.; Savéant, J.-M. Chem. Phys. Chem. 2000, 1, 199-205.
33. (b) Pause, L.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2001, 123, 4886-4895.
34. Argüello, J. E.; Peñéñory, A. B.; Rossi, R. A. J. Org. Chem. 2000, 65, 7175-7182.
35. (a) Pierini, A. B.; Baumgartner, M. T.; Rossi, R. A. Tetrahedron Lett. 1988, 29, 3451-3454.
36. (b) Petrillo, G.; Novi, M.; Dell'Erba, C. Tetrahedron Lett. 1989, 30, 6911-6912.
37. (c) Beugelmans, R.; Chbani, M. New J. Chem. 1994, 18, 949-952.
38. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J, P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
39. (b) Semiempirical calculations were performed by using the AM1/UHF method as implemented in the AMPAC package, from the Quamtum Chemistry Program Exchange (QCPE), Program No. 506.
40. Yuan, K.; Scott, W. J. J. Org. Chem. 1990, 55, 6188-6194.
41. Organic Syntheses; Baumgarten, Ed.; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 753.
42. Lukach, A. E.; Santiago, A. N.; Rossi, R. A. J. Phys. Org. Chem. 1994, 7, 610-614.
43. Rosowsky, A.; Chen, K. N.; Papathanasopoulos, N.; Modest, E. J. J. Heterocycl. Chem. 1972, 9, 263-273.