Antioxidant activity of o-bisphenols: The role of intramolecular hydrogen bonding

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5198-5204

  Amorati, Riccardo ^a   Lucarini, Marco ^a   Mugnaini, Veronica ^a   Pedulli, Gian Franco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION ENTHALPY (BDE);

ANTIOXIDANTS; BONDING; DISSOCIATION; ENTHALPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; PARAMAGNETIC RESONANCE; REACTION KINETICS; THERMODYNAMICS;

PHENOLS;

2 BISPHENOL DERIVATIVE; 2,2' ETHYLIDENEBIS(4,6 DI TERT BUTYLPHENOL); 2,2' METHYLENEBIS(6 TERT BUTYL 4 METHYLPHENOL); 4,4' METHYLENEBIS(2,6 DI TERT BUTYLPHENOL); PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; DISSOCIATION CONSTANT; ELECTRON SPIN RESONANCE; ENTHALPY; HYDROGEN BOND; REACTION ANALYSIS;

ANTIOXIDANTS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN BONDING; KINETICS; MOLECULAR STRUCTURE; PHENOLS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 0037871887     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342931     Document Type: Article

References (39)

1. Denisov, E. T.; Khudyakov, I. V. Chem. Rev. 1987, 87, 1313-1357.
2. (a) Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6472-6477.
3. (b) Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053-7065.
4. (a) Rice-Evans, C. A.; Miller, N. J.; Paganga, J. Free Rad. Biol. Med. 1996, 20, 933-956.
5. (b) Pietta, P. G. J. Nat. Prod. 2000, 63, 1035-1 42.
6. Brigati, G., Lucarini, M.; Mugnaini, V.; Pedulli, G. F. J. Org. Chem. 2002, 67, 4828-4832.
7. (a) Wright, J. S.; Johnson, E. R.; DiLabio, G. A. J. Am. Chem. Soc. 2001, 123, 1173-1183.
8. (b) de Heer, M. I.; Korth, H.; Mulder, P. J. Org. Chem. 1999, 64, 6969-6975.
9. (c) de Heer, M. I.; Mulder, P.; Korth, H.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 2000, 122, 2355-2360.
10. (a) Barclay, L. C. R.; Edwards, C. E.; Vinquist, M. R. J. Am. Chem. Soc. 1999, 121, 6226-6231.
11. (b) Pedrielli, P.; Pedulli, G. F.; Skibsted, L. H. J. Agric. Food Chem. 2001, 49, 3034-3040.
12. (c) Lucarini, M.; Mugnaini, V.; Pedulli, G. F. J. Org. Chem. 2002, 67, 928-931.
13. Lucarini, M.; Pedulli, G. F.; Valgimigli, L.; Amorati, R.; Minisci, F. J. Org. Chem. 2001, 66, 5456-5462.
14. Foti, M. C.; Johnson, E. R.; Vinquist, M. R.; Wright, J. S.; Barclay, L. C. R.; Ingold, K. U. J. Org. Chem. 2002, 67, 5190-5196. Foti, M. C.; Barclay, L. R. C., Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 12881-12888.
15. Foti, M. C.; Johnson, E. R.; Vinquist, M. R.; Wright, J. S.; Barclay, L. C. R.; Ingold, K. U. J. Org. Chem. 2002, 67, 5190-5196. Foti, M. C.; Barclay, L. R. C., Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 12881-12888.
16. Amorati, R.; Pedulli, G. F.; Valgimigli, L.; Attanasi, O. A.; Filippone, P.; Fiorucci, C.; Saladino, R. J. Chem. Soc., Perkin Trans. 2 2001, 2142-2146.
17. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1967, 45, 793-802.
18. Howard, J. A. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Chapter 12, Volume 2.
19. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1965, 43, 2729-2736.
20. Pryor, W. A.; Strickland, T.; Church, D. F. J. Am. Chem. Soc. 1988, 110, 2224-2229.
21. Darley-Usmar, V. M.; Hersey. A.; Garland, L. G. Biochem. Pharmacol. 1989, 38, 1465-1469.
22. inh the stoichiometric coefficient was assumed to be 2 for both the inhibited and retarded periods since the reactivity of the two hydroxyl groups is so different that they behave independently of one another.
23. Lucarini, M.; Pedrielli, P.; Pedulli, G. F.; Cabiddu, S.; Fattuoni, C. J. Org. Chem. 1996, 61, 9259-9263.
24. Avila, D. V.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 2929-2930. Wayner, D. D. M.; Lusztyk, J.; Pagé, D.; Ingold, K. U.; Mulder, P.; Laarhoven, L. J. J.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737-8744.
25. Avila, D. V.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 2929-2930. Wayner, D. D. M.; Lusztyk, J.; Pagé, D.; Ingold, K. U.; Mulder, P.; Laarhoven, L. J. J.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737-8744.
26. Ingold, K. U. Can. J. Chem. 1960, 38, 1092. Ingold, K. U.; Taylor, D. R. Can. J. Chem. 1961, 39, 471. Ingold, K. U. Can. J. Chem. 1962, 40, 111.
27. Ingold, K. U. Can. J. Chem. 1960, 38, 1092. Ingold, K. U.; Taylor, D. R. Can. J. Chem. 1961, 39, 471. Ingold, K. U. Can. J. Chem. 1962, 40, 111.
28. Ingold, K. U. Can. J. Chem. 1960, 38, 1092. Ingold, K. U.; Taylor, D. R. Can. J. Chem. 1961, 39, 471. Ingold, K. U. Can. J. Chem. 1962, 40, 111.
29. Pedrielli, P.; Pedulli, G. F. Gazzetta 1997, 127, 509-512.
30. Franchi, P.; Lucarini, M.; Pedulli, G. F.; Valgimigli, L.; Lunelli, B. J. Am. Chem. Soc. 1999, 121, 507-514.
31. Kovac, S.; Solcaniova, E.; Baxa, J. Tetrahedron 1971, 27, 2823-2830. Kanala, A.; Kovac, S. Tetrahedron 1975, 31, 2089-2090.
32. Kovac, S.; Solcaniova, E.; Baxa, J. Tetrahedron 1971, 27, 2823-2830. Kanala, A.; Kovac, S. Tetrahedron 1975, 31, 2089-2090.
33. Katsyuba, S.; Chernova, A.; Schmutzler, R.; Grunenberg, J. J. Chem. Soc., Perkin Trans. 2 2002, 67-71.
34. Experiments were performed at high concentration of antioxidant and azoinitiator (AIBN) in the absence of any oxidizable substrate in order to simplify the MS spectra.
35. Whitehouse, C. M.; Dreyer, R, N.; Yamashita, M.; Fenn, J. B. Anal. Chem. 1985, 57, 675.
36. Borges dos Santos, R. M.; Martinho Simões, J. A. J. Phys. Chem. Ref. Data 1998, 27, 707-739.
37. 2Ar and CHMeAr (if properly oriented) and the OH group is comparable to that one between the OH and the methyl groups.
38. Zhang, H. Y.; Sun, Y. M.; Wang, X. L Chem. Eur. J. 2003, 9, 502-508.
39. Franchi, P.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. Chem-PhysChem 2002, 3, 789-793.