Acid Is Key to the Radical-Trapping Antioxidant Activity of Nitroxides

Journal of the American Chemical Society

Volumn 138, Issue 16, 2016, Pages 5290-5298

  Haidasz, Evan A ^a   Meng, Derek ^a   Amorati, Riccardo ^b   Baschieri, Andrea ^b   Ingold, Keith U ^c   Valgimigli, Luca ^b   Pratt, Derek A ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANTS; CATALYSIS; CATALYST ACTIVITY; ELECTRON TRANSITIONS; IONS;

ACID-CATALYZED REACTIONS; ANTI-OXIDANT ACTIVITIES; BACK ELECTRON TRANSFER; DIFFUSION-CONTROLLED RATES; ELEVATED TEMPERATURE; HINDERED AMINE LIGHT STABILIZER; OXIDATIVE DEGRADATION; SYNTHETIC TRANSFORMATIONS;

FREE RADICAL REACTIONS;

2,2,6,6 TETRAMETHYLPIPERIDIN 1 OXYL; AMINE; CARBOXYLIC ACID; CHLOROBENZENE; HYDROCARBON; NITROXIDE; OXYGEN; PEROXY RADICAL; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; AUTOOXIDATION; DECOMPOSITION; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENVIRONMENTAL TEMPERATURE; MOLECULAR WEIGHT; REACTION ANALYSIS; TEMPERATURE;

EID: 84966425170     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b00677     Document Type: Article

References (54)

1. Ingold, K. Chem. Rev. 1961, 61, 563-589 10.1021/cr60214a002
2. Ingold, K. U.; Pratt, D. A. Chem. Rev. 2014, 114, 9022-9046 10.1021/cr500226n
3. Brownlie, I. T.; Ingold, K. U. Can. J. Chem. 1967, 45, 2427-2432 10.1139/v67-391
4. Sudnik, M. V.; Romantsev, M. F.; Shapiro, A. B.; Rozantsev, E. G. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1975, 24, 2702-2704 10.1007/BF01152883
5. Bolsman, T.; Blok, A.; Frijns, J. Recl. des Trav. Chim. des Pays-Bas 1978, 97, 310-312 10.1002/recl.19780971204
6. Allen, N. S. Chem. Soc. Rev. 1986, 15, 373-404 10.1039/cs9861500373
7. Gugumus, F. Polym. Degrad. Stab. 1993, 40, 167-215 10.1016/0141-3910(93)90208-Z
8. Pospisil, J. Adv. Polym. Sci. 1995, 124, 87-189 10.1007/BFb0025229
9. Samuni, A. M.; Goldstein, S.; Russo, A.; Mitchell, J. B.; Krishna, M. C.; Neta, P. J. Am. Chem. Soc. 2002, 124, 8719-8724 10.1021/ja017587h
10. Goldstein, S.; Merenyi, G.; Russo, A.; Samuni, A. J. Am. Chem. Soc. 2003, 125, 789-795 10.1021/ja028190w
11. Borisenko, G. G.; Martin, I.; Zhao, Q.; Amoscato, A. A.; Kagan, V. E. J. Am. Chem. Soc. 2004, 126, 9221-9232 10.1021/ja0495157
12. Wipf, P.; Xiao, J.; Jiang, J.; Belikova, N. A.; Tyurin, V.; Fink, M. P.; Kagan, V. E. J. Am. Chem. Soc. 2005, 127, 12460-12461 10.1021/ja053679l
13. Dikalova, A. E.; Bikineyeva, A. T.; Budzyn, K.; Nazarewicz, R. R.; McCann, L.; Lewis, W.; Harrison, D. G.; Dikalov, S. I. Circ. Res. 2010, 107, 106-116 10.1161/CIRCRESAHA.109.214601
14. Ji, J.; Kline, A. E.; Amoscato, A.; Samhan-Arias, A. K.; Sparvero, L. J.; Tyurin, V. A.; Tyurina, Y. Y.; Fink, B.; Manole, M. D.; Puccio, A. M.; Okonkwo, D. O.; Cheng, J. P.; Alexander, H.; Clark, R. S. B.; Kochanek, P. M.; Wipf, P.; Kagan, V. E.; Bayir, H. Nat. Neurosci. 2012, 15, 1407-1413 10.1038/nn.3195
15. Canistro, D.; Boccia, C.; Falconi, R.; Bonamassa, B.; Valgimigli, L.; Vivarelli, F.; Soleti, A.; Genova, M. L.; Lenaz, G.; Sapone, A.; Zaccanti, F.; Abdel-Rahman, S. Z.; Paolini, M. J. Gerontol. A Biol. Sci. Med. Sci. 2015, 70, 936-943 10.1093/gerona/glu160
16. Kovtun, G. A.; Aleksandrov, A. L.; Golubev, V. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1974, 23, 2115-2121 10.1007/BF00921266
17. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992-4996 10.1021/ja00039a006
18. Sobek, J.; Martschke, R.; Fischer, H. J. Am. Chem. Soc. 2001, 123, 2849-2857 10.1021/ja0036460
19. Gryn'ova, G.; Ingold, K. U.; Coote, M. L. J. Am. Chem. Soc. 2012, 134, 12979-12988 10.1021/ja3006379
20. Bolsman, T.; Blok, A.; Frijns, J. Recl. des Trav. Chim. des Pays-Bas 1978, 97, 313-319 10.1002/recl.19780971205
21. This can be found throughout the literature, in particular, the two areas where nitroxide radical chemistry is particularly important. Radical polymerization: Matyjaszewski, K.; Davis, T. P. Handbook of Radical Polymerization; Wiley: Hoboken, NJ, 2002.
22. Spin-labeling: Kocherginsky, N.; Swartz, H. M. Nitroxide Spin Labels: Reactions in Biology and Chemistry; CRC Press: Boca Raton, FL, 1995.
23. Amorati, R.; Pedulli, G. F.; Pratt, D. A.; Valgimigli, L. Chem. Commun. (Cambridge, U. K.) 2010, 46, 5139-5141 10.1039/c0cc00547a
24. A role for the acid-mediated disproportionation of TEMPO to produce the corresponding hydroxylamine (and oxoammonium ion) was ruled out on kinetic grounds (see ref 13). However, it is also possible that the reaction takes place by a coupled proton-electron transfer, wherein a proton is transferred from the acid to the peroxyl radical concerted with the movement of an electron from TEMPO to the peroxyl. Since we found that there is a primary kinetic isotope effect on these reactions, a H atom must be in flight in the rate-determining step of the reaction, precluding any rapid pre-equilibrium between peroxyl and protonated peroxyl, such as that which is involved when phenols react with peroxyl radicals under acidic conditions. See: Valgimigli, L.; Amorati, R.; Petrucci, S.; Pedulli, G. F.; Hu, D.; Hanthorn, J. J.; Pratt, D. A. Angew. Chem., Int. Ed. 2009, 48, 8348-8351 10.1002/anie.200903360
25. Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781 10.1021/ar010075n
26. Bailey, W. F.; Bobbitt, J. M.; Wiberg, K. B. J. Org. Chem. 2007, 72, 4504-4509 10.1021/jo0704614
27. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357-2367 10.1021/ja3117203
28. Ryland, B. L.; McCann, S. D.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2014, 136, 12166-12173 10.1021/ja5070137
29. Denisov, E. T. Polym. Degrad. Stab. 1991, 34, 325-332 10.1016/0141-3910(91)90126-C
30. Baran has invoked this electron transfer in a mechanistic proposal for the guided desaturation of unactivated alkanes. See: Voica, A.-F.; Mendoza, A.; Gutekunst, W. R.; Fraga, J. O.; Baran, P. S. Nat. Chem. 2012, 4, 629-635 10.1038/nchem.1385
31. Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822-2827 10.1063/1.477924
32. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095-5099 10.1021/ja00353a039
33. Burton, G. W.; Doba, T.; Gabe, E.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053-7065 10.1021/ja00310a049
34. Ma, Y.; Loyns, C.; Price, B.; Chechik, V. Org. Biomol. Chem. 2011, 9, 5573-5578 10.1039/c1ob05475a
35. Jensen, R. K.; Korcek, S.; Mahoney, L. R.; Zinbo, M. J. Am. Chem. Soc. 1979, 101, 7574-7584 10.1021/ja00519a018
36. Shah, R.; Haidasz, E. A.; Valgimigli, L.; Pratt, D. A. J. Am. Chem. Soc. 2015, 137, 2440-2443 10.1021/ja5124144
37. Hanthorn, J.; Haidasz, E.; Gebhardt, P.; Pratt, D. A. Chem. Commun. 2012, 48, 10141-10143 10.1039/c2cc35214a
38. Jensen, R. K.; Korcek, S.; Mahoney, L. R.; Zinbo, M. J. Am. Chem. Soc. 1981, 103, 1742-1749 10.1021/ja00397a026
39. Jalan, A.; Alecu, I. M.; Meana-Pañeda, R.; Aguilera-Iparraguirre, J.; Yang, K. R.; Merchant, S. S.; Truhlar, D. G.; Green, W. H. J. Am. Chem. Soc. 2013, 135, 11100-11114 10.1021/ja4034439
40. Shah, R.; Pratt, D. A. Manuscript in preparation.
41. 2, which they determined directly. See: Jensen, R. K.; Korcek, S.; Zinbo, M. Oxid. Commun. 1990, 13, 258-262
42. Up to 2.7 M of 2,2,6,6-tetramethyl-1-(2-propenyloxy)piperidine had no detectable influence on the product distribution in a methyl linoleate clocking experiment, which was carried out as described in: Roschek, B.; Tallman, K. A.; Rector, C. L.; Gillmore, J. G.; Pratt, D. A.; Punta, C.; Porter, N. A. J. Org. Chem. 2006, 71, 3527-3532 10.1021/jo0601462
43. -1. See: Howard, J. A.; Ingold, K. U. Can. J. Chem. 1970, 48, 873-880 10.1139/v70-144
44. Bennett, J. E.; Eyre, J. A.; Summers, R. J. Chem. Soc., Perkin Trans. 2 1974, 797-800 10.1039/p29740000797
45. Adamic, K.; Dunn, M.; Ingold, K. U. Can. J. Chem. 1969, 47, 287-294 10.1139/v69-040
46. Jensen, R. K.; Korcek, S.; Zinbo, M.; Gerlock, J. L. J. Org. Chem. 1995, 60, 5396-5400 10.1021/jo00122a014
47. Haidasz, E. A.; Shah, R.; Pratt, D. A. J. Am. Chem. Soc. 2014, 136, 16643-16650 10.1021/ja509391u
48. Pospisil, J. Polym. Degrad. Stab. 1991, 34, 85-109 10.1016/0141-3910(91)90113-6
49. Holan, M.; Jahn, U. Org. Lett. 2014, 16, 58-61 10.1021/ol403016p
50. Ikeda, H.; Hoshi, Y.; Namai, H.; Tanaka, F.; Goodman, J. L.; Mizuno, K. Chem.-Eur. J. 2007, 13, 9207-9215 10.1002/chem.200700820
51. Valgimigli, L.; Pedulli, G. F.; Paolini, M. Free Radical Biol. Med. 2001, 31, 708-716 10.1016/S0891-5849(01)00490-7
52. Amorati, R.; Pedulli, G. F.; Valgimigli, L. Org. Biomol. Chem. 2011, 9, 3792-3800 10.1039/c1ob05334e
53. Knight, H. B.; Swern, D. Org. Synth. 1954, 34, 90-91 10.15227/orgsyn.034.0090
54. Benson, S. W. Thermochemical Kinetics, 2 nd ed.; Wiley: New York, 1976.