Polyphenols deriving from chalcones: Investigations of redox activities

Journal of Physical Chemistry B

Volumn 109, Issue 49, 2005, Pages 23720-23729

  Cotelle, Nicole ^a   Hapiot, Philippe ^c   Pinson, Jean ^b   Rolando, Christian ^a   Vézin, Hervé ^a  

^a CNRS   (France)

^b Alchimer SA   (France)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANTS; OXIDATION; POLYMERS; REACTION KINETICS; REDOX REACTIONS; THERMODYNAMICS;

DENSITY FUNCTIONAL THEORY; PHENOLATES; POLYPHENOLS; REDOX BEHAVIOR;

PHENOLS;

EID: 30544454261     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0550661     Document Type: Article

References (52)

1. Star, A. E.; Mabry, T. J. Phytochemistry 1971, 10, 2812.
2. Stevens, J. F.; Taylor, A. W.; Nickerson, G. B.; Ivancic, M.; Henning, J.; Haunold, A.; Deinzer, M. L. Phytochemistry 2000, 53, 759.
3. Satyanarayana, K.; Rao, M. N. A. Indian Drugs 1993, 30, 313.
4. Shibata, S. Stem Cells 1994, 12, 44.
5. Dhar, D. N. The Chemistry of Chalcones and Related Compounds; Wiley: New York, 1981
6. Ruby, J. A.; Sukumaran, K.; Kuttan, G.; Rao, M. N. A.; Subbaraju, V.; Kuttan, R. Cancer Lett. 1995, 97, 33.
7. Maggiolini, M.; Statti, G.; Vivacqua, A.; Gabriele, S.; Rago, V.; Loizzo, M.; Menichini, F.; Amdo, S. J. Steroid Biochem. Mol. Biol. 2002, 82, 315.
8. Tamir, S.; Eizenberg, M.; Somjen, D.; Izrael, S.; Vaya, J. J. Steroid Biochem. Mol. Biol. 2001, 78, 291.
9. (a) Lebeau, J.; Furman, C.; Bernier, J. L.; Duriez, P.; Teissier, E.; Cotelle, N. Free Radical Biol. Med. 2000, 29, 900.
10. (b) Furman, C.; Lebeau, J.; Fruchart, J.; Bernier, J.; Duriez, P.; Cotelle, N.; Teissier, E. J. Biochem. Mol. Toxicol. 2001, 15, 270.
11. Lebeau, J.; Neviere, R.; Cotelle, N. Bioorg. Med. Chem. Lett. 2001, 11, 23.
12. (a) Kashima, M. Chem. Pharm. Bull. 1999, 47, 279.
13. (b) Hanasaki, Y.; Ogawa S.; Fukui, S. Free Radical Biol. Med. 1994, 16, 845.
14. (c) Salah, N.; Miller, N. J.; Paganga, G.; Tijburg, L.; Bolwell, G. P.; Rice-Evans, C. Arch. Biochem. Biophys. 1995, 322, 339.
15. (d) Rice-Evans, C. Biochem. Soc. Symp. 1994, 61, 103.
16. (e) Vinson, J. A.; Hontz, B. A. J. Agric. Food Chem. 1995, 43, 401.
17. (f) Nakao, M.; Takio, S.; Ono, K. Phytochemistry 1998, 49, 2379.
18. Cren-Olivé, C.; Hapiot, P.; Pinson, J.; Rolando, C. J. Am. Chem. Soc. 2002, 124, 14027.
19. Hapiot, P.; Pinson, J.; Francesh, C.; Mhamdi, F.; Rolando, C.; Neta, P. J. Phys. Chem. 1994, 98, 2641.
20. Fulcrand, H.; Hapiot, P.; Neta, P.; Pinson, J.; Rolando, C. Analusis 1997, 25, M38.
21. Wittman, H.; Uragg, H. Monatsh. Chem. 1967, 98, 404.
22. Lmafuku, K.; Honda, M.; McOmie, J. F. W. Synthesis 1987, 2, 199.
23. Jain, A. C.; Mehta, A. Tetrahedron 1985, 41, 5933.
24. Garreau, D.; Savéant, J.-M. J. Electroanal. Chem. 1972, 35, 309.
25. Rudolph, M.; Reddy, D. P.; Feldberg, S. W. Anal. Chem. 1994, 66, 589A.
26. 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.; Kiene, 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.04; Gaussian, Inc.: Wallingford, CT, 2004.
27. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
28. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 16, 217.
29. (a) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327
30. (b) For a general review about solvation methods see: Cramer, J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161.
31. a, values.
32. (a) Andrieux, C. P.; Savéant, J. M. In Investigations of Rates and Mechanisms of Reactions; Bernasconi, C. F., Ed.; John Wiley and Sons: New York, 1986; Vol. 6, Part 2, pp 305-390.
33. (b) Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2nd ed.; John Wiley and Sons: New York, 2000.
34. 26b
35. (b) Nadjo, L.; Savéant, J. M. J. Electroanal. Chem. 1973, 48, 113.
36. (c) Andrieux, C. P.; Nadjo, L.; Savéant, J.-M. J. Electroanal. Chem. 1973, 42, 223.
37. (d) Richards, J. A.; Whitson, P. E.; Evans, D. H. J. Electroanal. Chem. 1915, 63, 311.
38. Hapiot, P.; Pinson, J.; Yousfi, N. New J. Chem. 1992, 16, 877.
39. -1.
40. Due to its lower energy, only the radical localized on ring A is experimentally produced.
41. (a) Bordwell F. G.; McCallum, R. J.; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424.
42. (b) Bausch, M. J.; Gostowski, R.; Guadalupe-Fasano, C.; Selmarten, D.; Vaughn, A.; Wang, L.-H. J. Org. Chem. 1991, 56, 7192.
43. Fu, Y.; Liu, R., Liu, L.; Guo, Q.-X. J. Phys. Org. Chem. 2004, 17, 282.
44. elec(anion)) calculated with and without hydrogen bonds with the data of Table 5.
45. + followed by rapid deprotonation then a second irreversible oxidation).
46. 34b-f slower kinetics and thus larger activation energies are related to larger solvation changes accompanying the electron transfer and are generally observed when the charge is localized.
47. (b) Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
48. (c) Marcus, R. A. J. Chem. Phys. 1956, 24, 979.
49. (d) Hush, N. S. J. Chem. Phys. 1958, 28, 962.
50. (e) Hush, N. S. Trans. Faraday Soc. 1961, 57, 557.
51. (f) Marcus, R. A. J. Chem. Phys. 1965, 43, 679.
52. pa3 of Table 2. This behavior confirms that the two rings are independent (nonconjugated) and are oxidized separately, the more easily oxidized phenol of ring A being oxidized first followed by the phenol of ring B.