The kinetics of thiyl radical-induced reactions of monounsaturated fatty acid esters

Journal of the American Chemical Society

Volumn 124, Issue 43, 2002, Pages 12816-12823

  Chatgilialoglu, Chryssostomos ^b   Altieri, Alessio ^b   Fischer, Hanns ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FATTY ACIDS; ISOMERIZATION; ISOMERS; RADIATION; RADIOLYSIS; RATE CONSTANTS;

RADIAL STRUCTURES;

ESTERS;

ALKENE DERIVATIVE; FATTY ACID ESTER; MONOUNSATURATED FATTY ACID; OLEIC ACID; RADICAL; TERT BUTYL ALCOHOL; THIOL DERIVATIVE; THIYL RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; ISOMERISM; RADIOLYSIS; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0037202139     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027428d     Document Type: Article

References (46)

1. Walling, C. Free Radicals in Solution; Wiley: New York, 1957.
2. Chatgilialoglu, C.; Bertrand, M. P.; Ferreri, C. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: New York, 1999. Chatgilialoglu, C.; Guerra, M. In Supplement S: The Chemistry of Sulphur-Containing Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1993.
3. Chatgilialoglu, C.; Bertrand, M. P.; Ferreri, C. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: New York, 1999. Chatgilialoglu, C.; Guerra, M. In Supplement S: The Chemistry of Sulphur-Containing Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1993.
4. Pallen, R. H.; Sivertz, C. Can. J. Chem. 1957, 35, 723. Graham, D. M.; Mieville, R. L.; Sivertz, C. Can. J. Chem. 1964, 42, 2239. Graham, D. M.; Mieville, R. L.; Pallen, R. H.; Sivertz, C. Can. J. Chem. 1964, 42, 2250.
5. Pallen, R. H.; Sivertz, C. Can. J. Chem. 1957, 35, 723. Graham, D. M.; Mieville, R. L.; Sivertz, C. Can. J. Chem. 1964, 42, 2239. Graham, D. M.; Mieville, R. L.; Pallen, R. H.; Sivertz, C. Can. J. Chem. 1964, 42, 2250.
6. Pallen, R. H.; Sivertz, C. Can. J. Chem. 1957, 35, 723. Graham, D. M.; Mieville, R. L.; Sivertz, C. Can. J. Chem. 1964, 42, 2239. Graham, D. M.; Mieville, R. L.; Pallen, R. H.; Sivertz, C. Can. J. Chem. 1964, 42, 2250.
7. Walling, C.; Helmreich, W. J. Am. Chem. Soc. 1959, 81, 1144.
8. Sgoutas, D. S.; Kummerow, F. A. Lipids 1969, 4, 283.
9. Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459. Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Mulazzani, Q. G.; Landi, L. J. Am. Chem. Soc. 2000, 122, 4593. Ferreri, C.; Costantino, C.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. Chem. Commun. 1999, 5, 407. Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
10. Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459. Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Mulazzani, Q. G.; Landi, L. J. Am. Chem. Soc. 2000, 122, 4593. Ferreri, C.; Costantino, C.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. Chem. Commun. 1999, 5, 407. Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
11. Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459. Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Mulazzani, Q. G.; Landi, L. J. Am. Chem. Soc. 2000, 122, 4593. Ferreri, C.; Costantino, C.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. Chem. Commun. 1999, 5, 407. Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
12. Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459. Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Mulazzani, Q. G.; Landi, L. J. Am. Chem. Soc. 2000, 122, 4593. Ferreri, C.; Costantino, C.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. Chem. Commun. 1999, 5, 407. Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
13. Adhikari, S.; Sprinz, H.; Brede, O. Res. Chem. Intermed. 2001, 4, 5, 549. Sprinz, H.; Schwinn, J.; Naumov, S.; Brede, O. Biochim. Biophys. Acta 2000, 1483, 91. Schwinn, J.; Sprinz, H.; Droessler, K.; Leistner, S.; Brede, O. Int. J. Radiat. Biol. 1998, 74, 359.
14. Adhikari, S.; Sprinz, H.; Brede, O. Res. Chem. Intermed. 2001, 4, 5, 549. Sprinz, H.; Schwinn, J.; Naumov, S.; Brede, O. Biochim. Biophys. Acta 2000, 1483, 91. Schwinn, J.; Sprinz, H.; Droessler, K.; Leistner, S.; Brede, O. Int. J. Radiat. Biol. 1998, 74, 359.
15. Adhikari, S.; Sprinz, H.; Brede, O. Res. Chem. Intermed. 2001, 4, 5, 549. Sprinz, H.; Schwinn, J.; Naumov, S.; Brede, O. Biochim. Biophys. Acta 2000, 1483, 91. Schwinn, J.; Sprinz, H.; Droessler, K.; Leistner, S.; Brede, O. Int. J. Radiat. Biol. 1998, 74, 359.
16. (a) The effectiveness of Z-E isomerization by thiyl radicals in the presence of the most common antioxidants vitamins has also been addressed, see: Chatgilialoglu, C.; Zambonin, L.; Altieri, A.; Ferreri, C.; Mulazzani, Q. G.; Landi, L. Free Radical Biol. Med. 2002, in press.
17. 2 radical induces Z-E isomerization of arachidonic acid within cellular phospholidids, see: Jiang, H.; Kruger, N.; Lahiri, D. R.; Wang, D.; Vatèle, J.-M.; Balazy, M. J. Biol. Chem. 1999, 274, 16235.
18. Schoeneich, C.; Asmus, K.-D.; Dillinger, U.; von Bruchhausen, F. Biochem. Biophys. Res. Commun. 1989, 161, 113. Schoeneich, C.; Bonifacic, M.; Dillinger, U.; Asmus, K.-D. In Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; p 367. Schoeneich, C.; Dillinger, U.; von Bruchhausen, F.; Asmus, K.-D. Arch. Biochem. Biophys. 1992, 292, 456.
19. Schoeneich, C.; Asmus, K.-D.; Dillinger, U.; von Bruchhausen, F. Biochem. Biophys. Res. Commun. 1989, 161, 113. Schoeneich, C.; Bonifacic, M.; Dillinger, U.; Asmus, K.-D. In Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; p 367. Schoeneich, C.; Dillinger, U.; von Bruchhausen, F.; Asmus, K.-D. Arch. Biochem. Biophys. 1992, 292, 456.
20. Schoeneich, C.; Asmus, K.-D.; Dillinger, U.; von Bruchhausen, F. Biochem. Biophys. Res. Commun. 1989, 161, 113. Schoeneich, C.; Bonifacic, M.; Dillinger, U.; Asmus, K.-D. In Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; p 367. Schoeneich, C.; Dillinger, U.; von Bruchhausen, F.; Asmus, K.-D. Arch. Biochem. Biophys. 1992, 292, 456.
21. -1 at room temperature in n-hexane. Ito, O.; Matsuda, M. Bull. Chem. Soc. Jpn. 1978, 51, 427.
22. Tronche, C.; Martinez, F. N.; Homer, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 37, 5845. Enzinas, M. V.; Wagner, P. J.; Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 1357.
23. Tronche, C.; Martinez, F. N.; Homer, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 37, 5845. Enzinas, M. V.; Wagner, P. J.; Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 1357.
24. Newcomb, M.; Choi, S.-Y.; Homer, J. H. J. Org. Chem. 1999, 64, 1225.
25. Newcomb, M. Tetrahedron 1993, 49, 1151. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
26. Newcomb, M. Tetrahedron 1993, 49, 1151. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
27. Chatgilialoglu, C.; Dickhaut, J.; Giese, B. J. Org. Chem. 1991, 56, 6399.
28. Landolt-Boernstein: Zahlenwerte und Funktionen aus Physik, Chemie, Astronomie. Geophysik und Technik, 6th Ed.; Schaefer, K., Lax, E., Eds.; Springer: Berlin. 1961; Vol 2, Part 4, p 263.
29. AH = -4.4 kJ/mol: Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref Data 1988, 17, Supplement 1.
30. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1969, 47, 2529. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1969, 47, 2719. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1970, 48, 2137.
31. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1969, 47, 2529. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1969, 47, 2719. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1970, 48, 2137.
32. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1969, 47, 2529. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1969, 47, 2719. Graham, D. M.; Soltys, J. F. Can. J. Chem. 1970, 48, 2137.
33. 18
34. Ito, O. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: New York, 1999.Ito, O. In General Aspects of the Chemistry of Free Radicals; Afassi, Z. B., Ed.; Wiley: New York, 1999. Ito, O.; Matsuda, M. Bull. Chem. Soc. Jpn. 1978, 51, 427. Ito, O.; Matsuda, M. J. Am. Chem. Soc. 1979, 101, 1815, 5732.
35. Ito, O. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: New York, 1999.Ito, O. In General Aspects of the Chemistry of Free Radicals; Afassi, Z. B., Ed.; Wiley: New York, 1999. Ito, O.; Matsuda, M. Bull. Chem. Soc. Jpn. 1978, 51, 427. Ito, O.; Matsuda, M. J. Am. Chem. Soc. 1979, 101, 1815, 5732.
36. Ito, O. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: New York, 1999.Ito, O. In General Aspects of the Chemistry of Free Radicals; Afassi, Z. B., Ed.; Wiley: New York, 1999. Ito, O.; Matsuda, M. Bull. Chem. Soc. Jpn. 1978, 51, 427. Ito, O.; Matsuda, M. J. Am. Chem. Soc. 1979, 101, 1815, 5732.
37. Ito, O. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: New York, 1999.Ito, O. In General Aspects of the Chemistry of Free Radicals; Afassi, Z. B., Ed.; Wiley: New York, 1999. Ito, O.; Matsuda, M. Bull. Chem. Soc. Jpn. 1978, 51, 427. Ito, O.; Matsuda, M. J. Am. Chem. Soc. 1979, 101, 1815, 5732.
38. Wagner, P. J.; Sedon, J. H.; Lindstrom, M. J. J. Am. Chem. Soc. 1978, 100, 2579.
39. Balla, R. J.; Weiner, B. R.; Nelson, H. H. J. Am. Chem. Soc. 1987, 109, 4808.
40. Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340.
41. McPhee, D. J.; Campredon, M.; Lesage, M.; Griller, D. J. Am. Chem. Soc. 1989, 111, 7563. Griller, D.; Martinho Simoes, J. A. In Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; p 327.
42. McPhee, D. J.; Campredon, M.; Lesage, M.; Griller, D. J. Am. Chem. Soc. 1989, 111, 7563. Griller, D.; Martinho Simoes, J. A. In Sulfur Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; p 327.
43. Davies, A. G.; Roberts, B. P. J. Chem, Soc. B 1972, 1830.
44. Salerni, O. L.; Clark, R. N.; Smart, B. E. J. Chem. Soc. C 1996, 645.
45. Trost, B. M.; Ziman, S. D. J. Org. Chem. 1973, 38, 932.
46. Spinks, J. W. T.; Woods, R. J. An Introduction to Radiation Chemistry, 3rd Ed.; Wiley: New York, 1990; p 100.