Competition H(D) kinetic isotope effects in the autoxidation of hydrocarbons

Journal of the American Chemical Society

Volumn 137, Issue 1, 2015, Pages 94-97

  Muchalski, Hubert ^a   Levonyak, Alexander J ^a   Xu, Libin ^a   Ingold, Keith U ^b   Porter, Ned A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ABSTRACTING; ATOMS; CARRIER MOBILITY; ISOTOPES; OXIDATION; QUANTUM THEORY;

COMPETITION REACTIONS; H-ATOM ABSTRACTION; HYDROGEN-ATOM TRANSFER; KINETIC ISOTOPE EFFECTS; PEROXYL RADICAL; QUANTUM-MECHANICAL TUNNELING; VARIOUS SUBSTRATES; ZERO-POINT ENERGIES;

FREE RADICAL REACTIONS;

DEUTERIUM; HYDROCARBON; HYDROGEN; ISOTOPE; PEROXY RADICAL; TETRALIN DERIVATIVE; PERHYDROXYL RADICAL; PEROXIDE;

ARTICLE; ATOMIC PARTICLE; AUTOOXIDATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; INTRAMOLECULAR COMPETITION; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM CHEMISTRY; REACTION ANALYSIS; CHEMISTRY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

DEUTERIUM; HYDROCARBONS; HYDROGEN; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEROXIDES;

EID: 84921056901     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja511434j     Document Type: Article

References (45)

1. Ingold, K. U. Acc. Chem. Res. 1969, 2, 1-9
2. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739-7742
3. Johnston, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickreyma, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594-4596
4. Giese, B. Angew. Chem., Int. Ed. 1983, 22, 753-764
5. Newcomb, M. Tetrahedron 1993, 49, 1151-1176
6. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323
7. Roschek, B., Jr.; Tallman, K. A.; Rector, C. L.; Gillmore, J. G.; Pratt, D. A.; Punta, C.; Porter, N. A. J. Org. Chem. 2006, 71, 3527-3532
8. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1965, 43, 2729-2736
9. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1965, 43, 2737-2743
10. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1966, 44, 1119-1130
11. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1966, 44, 1113-1118
12. Howard, J. A.; Ingold, K. U.; Symonds, M. Can. J. Chem. 1968, 46, 1017-1022
13. Howard, J. A.; Schwalm, W. J.; Ingold, K. U. In Oxidation of Organic Compounds; American Chemical Society: Washington, DC, 1968; Vol. 75, pp 6-23.
14. Russell, G. A. J. Am. Chem. Soc. 1955, 77, 4583-4590
15. Xu, L.; Davis, T. A.; Porter, N. A. J. Am. Chem. Soc. 2009, 131, 13037-13044
16. Pratt, D. A.; Tallman, K. A.; Porter, N. A. Acc. Chem. Res. 2011, 44, 458-467
17. Russell, G. A. J. Am. Chem. Soc. 1957, 79, 3871-3877
18. Hill, S.; Hirano, K.; Shmanai, V.; Marbois, B.; Vidovic, D.; Bekish, A.; Kay, B.; Tse, V.; Fine, J.; Clarke, C. F.; Shchepinov, M. S. Free. Radic. Biol. Med. 2011, 50, 130
19. Shchepinov, M. S.; Chou, V. P.; Pollock, E.; Langston, J. W.; Cantor, C. R.; Molinari, R. J.; Manning-Bog, A. B. Toxicol. Lett. 2011, 207, 97
20. Hill, S.; Lamberson, C. R.; Xu, L.; To, R.; Tsui, H. S.; Shmanai, V. V.; Bekish, A. V.; Awad, A. M.; Marbois, B. N.; Cantor, C. R.; Porter, N. A.; Clarke, C. F.; Shchepinov, M. S. Free. Radic. Biol. Med. 2012, 53, 893
21. Muchalski, H.; Xu, L.; Porter, N. A. Org. Biomol. Chem. 2014, 10.1039/C4OB02377C
22. Simonian, N. A.; Coyle, J. T. Annu. Rev. Pharmacol. Toxicol. 1996, 36, 83-106
23. Hollyfield, J. G.; Bonilha, V. L.; Rayborn, M. E.; Yang, X.; Shadrach, K. G.; Lu, L.; Ufret, R. L.; Salomon, R. G.; Perez, V. L. Nat. Med. 2008, 14, 194-198
24. Yin, H.; Xu, L.; Porter, N. A. Chem. Rev. 2011, 111, 5944-5972
25. Xu, L.; Korade, Z.; Rosado, D. A.; Liu, W.; Lamberson, C. R.; Porter, N. A. J. Lipid Res. 2011, 52, 1222-1233
26. Pascal, R. A.; Baum, M. W.; Wagner, C. K.; Rodgers, L. R.; Huang, D. S. J. Am. Chem. Soc. 1986, 108, 6477-6482
27. Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357-9358
28. Zhang, B. L.; Pionnier, S. J. Phys. Org. Chem. 2001, 14, 239-246
29. Hanzlik, R. P.; Hogberg, K.; Moon, J. B.; Judson, C. M. J. Am. Chem. Soc. 1985, 107, 7164-7167
30. Hanzlik, R. P.; Schaefer, A. R.; Moon, J. B.; Judson, C. M. J. Am. Chem. Soc. 1987, 109, 4926-4930
31. Green, M. M.; Boyle, B. A.; Vairamani, M.; Mukhopadhyay, T.; Saunders, W. H.; Bowen, P.; Allinger, N. L. J. Am. Chem. Soc. 1986, 108, 2381-2387
32. Merrigan, S. R.; Le Gloahec, V. N.; Smith, J. A.; Barton, D. H. R.; Singleton, D. A. Tetrahedron Lett. 1999, 40, 3847-3850
33. Wu, A.; Mader, E. A.; Datta, A.; Hrovat, D. A.; Borden, W. T.; Mayer, J. M. J. Am. Chem. Soc. 2009, 131, 11985-11997
34. Ley, D.; Gerbig, D.; Schreiner, P. R. Org. Biomol. Chem. 2012, 10, 3781-3790
35. Amiri, S.; Reisenauer, H. P.; Schreiner, P. R. J. Am. Chem. Soc. 2010, 132, 15902-15904
36. Gerbig, D.; Reisenauer, H. P.; Wu, C. H.; Ley, D.; Allen, W. D.; Schreiner, P. R. J. Am. Chem. Soc. 2010, 132, 7273-7275
37. Ley, D.; Gerbig, D.; Schreiner, P. R. Chem. Sci. 2013, 4, 677-684
38. Schreiner, P. R.; Reisenauer, H. P.; Pickard, F. C.; Simmonett, A. C.; Allen, W. D.; Matyus, E.; Csaszar, A. G. Nature 2008, 453, 906-U942
39. Kozuch, S.; Zhang, X.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2013, 135, 17274-17277
40. Gonzalez-James, O. M.; Zhang, X.; Datta, A.; Hrovat, D. A.; Borden, W. T.; Singleton, D. A. J. Am. Chem. Soc. 2010, 132, 12548-12549
41. Klinman, J. P. Philos. Trans. R. Soc. London, Ser. B 2006, 361, 1323-1331
42. Klinman, J. P.; Kohen, A. Annu. Rev. Biochem. 2013, 82, 471-496
43. Weinberg, D. R.; Gagliardi, C. J.; Hull, J. F.; Murphy, C. F.; Kent, C. A.; Westlake, B. C.; Paul, A.; Ess, D. H.; McCafferty, D. G.; Meyer, T. J. Chem. Rev. 2012, 112, 4016
44. Caldin, E. F. Chem. Rev. 1969, 69, 135-156
45. Ingold, K. U. Quantum Mechanical Tunneling of Hydrogen Atoms in Some Simple Chemical Systems. In Hydrogen-Transfer Reactions; Hynes, J. T.; Klinman, J. P.; Limback, H.-H.; Schowen, R. L., Eds.; Wiley-VCH: Weinheim, Germany, 2006; Vol. 2, pp 875-893.