Kinetic Study of the Phthalimide N-Oxyl Radical in Acetic Acid. Hydrogen Abstraction from Substituted Toluenes, Benzaldehydes, and Benzyl Alcohols

Journal of Organic Chemistry

Volumn 68, Issue 24, 2003, Pages 9364-9370

  Koshino, Nobuyoshi ^a   Saha, Basudeb ^a   Espenson, James H ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MOLAR ABSORPTIVITY;

ACTIVATION ENERGY; ALCOHOLS; ALDEHYDES; ARGON; FREE RADICALS; ISOTOPES; OXIDATION; QUANTUM THEORY; RATE CONSTANTS; REACTION KINETICS;

ACETIC ACID;

ACETIC ACID; ARGON; BENZALDEHYDE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; N HYDROXYPHTHALIMIDE; PARA XYLENE; PHTHALIMIDE DERIVATIVE; PHTHALIMIDE N OXYL RADICAL; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ADSORPTION KINETICS; ANALYTIC METHOD; ARTICLE; ATMOSPHERE; CHEMICAL REACTION; CORRELATION ANALYSIS; KINETICS; QUANTUM CHEMISTRY; STATISTICAL SIGNIFICANCE; SUBSTITUTION REACTION;

EID: 0344391968     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0348017     Document Type: Article

References (66)

1. Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, 1996.
2. Partenheimer, W. Catal. Today 1995, 23, 69-158.
3. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
4. Tashiro, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2001, 343, 220-225.
5. Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810-6813.
6. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520-4526.
7. Ueda, C.; Noyama, M.; Ohmori, H.; Masui, M. Chem. Pharm. Bull. 1987, 35, 1372-1377.
8. After this manuscript was submitted, Pedulli et al. reported their work in ref 12.
9. Espenson, J. H. Chemical Kinetics and Reaction Mechanisms, 2nd ed.; McGraw-Hill: New York, 1995.
10. Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 3094-3098.
11. Minisci, F.; Punta, C.; Recupero, F.; Fontana, F.; Pedulli, G. F. Chem. Commun. 2002, 688-689.
12. Amorati, R.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F.; Minisci, F.; Recupero, F.; Fontana, F.; Astolfi, P.; Greci, L. J. Org. Chem. 2003, 68, 1747-1754.
13. Lemaire, H.; Rassat, A. Tetrahedron Lett. 1964, 2245-2248.
14. Ishii, Y.; Sakaguchi, S. Catal. Surv. Jpn. 1999, 3, 27-35.
15. The stoichiometry of the reaction is [Pb(IV)]:[NHPI] = 1:2.
16. 3, δ): 2.36 (s, 3H), 5.18 (s, 2H), 7.19 (d, 2H), 7.43 (d, 2H), 7.74 (m, 2H), 7.80 (m, 2H).
17. The changes in the spectra of NHPI and Pb(IV) can be neglected, because they are excess components and the reduced Pb-(II) is colorless.
18. Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992-4996.
19. Arends, I. W. C. E.; Mulder, P.; Clark, K. B.; Wayner, D. D. M. J. Phys. Chem. 1995, 99, 8182-8189.
20. Sobek, J.; Martschke, R.; Fischer, H. J. Am. Chem. Soc. 2001, 123, 2849-2857.
21. Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363-379.
22. Minisci, F.; Recupero, F.; Punta, C.; Gambarotti, C.; Antonietti, F.; Fontana, F.; Pedulli, G. F. Chem. Commun. 2002, 2496-2497.
23. Barshop, B. A.; Wrenn, R. F.; Frieden, C. Chemical Kinetic Simulation Software Ver. 4.0; Washington University, 1997.
24. Zhou, W.-J.; Hsieh, Y.-L.; Pratt, L. M.; Patten, T. E. Polym. Bull. 2001, 46, 43-50.
25. McDaniel, D. H.; Brown, H. C. J. Org. Chem. 1958, 23, 420-427.
26. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
27. Wentzel, B. B.; Donners, M. P. J.; Alsters, P. L.; Feiters, M. C.; Nolte, R. J. M. Tetrahedron 2000, 56, 7797-7803.
28. 2OH groups.
29. Pearson, R. E.; Martin, J. C. J. Am. Chem. Soc. 1963, 85, 354-355.
30. Walling, C.; Rieger, A. L.; Tanner, D. J. Am. Chem. Soc. 1963, 85, 3129-3134.
31. Metelski, P. D.; Espenson, J. H. J. Phys. Chem. A 2001, 105, 5881-5884.
32. Zavitsas, A. A.; Pinto, J. A. J. Am. Chem. Soc. 1972, 94, 7390-7396.
33. Zavitsas, A. A.; Fogel, G.; Halwagi, K. E.; Legotte, P. A. D. J. Am. Chem. Soc. 1983, 105, 6960-6962.
34. Zavitsas, A. A. J. Phys. Chem. A. 2002, 106, 5041-5042.
35. Pratt, D. A.; Wright, J. S.; Ingold, K. U. J. Am. Chem. Soc. 1999, 121, 4877-4882.
36. Lee, K. H. Tetrahedron 1968, 24, 4793-4803.
37. Yoshida, T.; Namba, K. Kogyo Kayaku Kyokai-shi 1968, 29, 353-360.
38. Solly, R. K.; Benson, S. W. J. Am. Chem. Soc. 1971, 93, 1592-1595.
39. Stavber, S.; Kosir, I.; Zupan, M. J. Org. Chem. 1997, 62, 4916-4920.
40. Fung, W.-H.; Yu, W.-Y.; Che, C.-M. J. Org. Chem. 1998, 63, 2873-2877.
41. Dijksman, A.; Marino-Gonzalez, A.; Mairata i Payeras, A.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826-6833.
42. Wen, Z.; Li, Z.; Shang, Z.; Cheng, J.-P. J. Org. Chem. 2001, 66, 1466-1472.
43. Koshino, N.; Cai, Y.; Espenson, J. H. J. Phys. Chem. A 2003, 107, 4262-4267.
44. Saha, B.; Koshino, N.; Espenson, J. H. Manuscript to be submitted.
45. Zakharov, I. V.; Geletii, Y. V.; Adamyan, V. A. Kinet. Catal. 1991, 32, 31-36.
46. Howard, J. A. In Peroxyl Radicals; Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester, 1997; p 283.
47. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: London, 1980.
48. Bell, R. P. Chem. Soc. Rev. 1974, 3, 513-544.
49. Kwart, H. Acc. Chem. Res. 1982, 15, 401-408.
50. The difference in KIE was discussed in ref 43.
51. Doba, T.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 3958-3963.
52. Otsuka, T.; Motozaki, W.; Nishikawa, K.; Endo, K. J. Mol. Struct. 2002, 615, 147-151.
53. Franchi, P.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. ChemPhysChem. 2002, 3, 789-793.
54. Shenderovich, I. G.; Kecki, Z.; Wawer, I.; Denisov, G. S. Spectrosc. Lett. 1997, 30, 1515-1523.
55. Mahoney, L. R.; DaRooge, M. A. J. Am. Chem. Soc. 1972, 94, 7002-7009.
56. Chenier, J. H. B.; Furimsky, E.; Howard, J. A. Can. J. Chem. 1974, 52, 3682-3688.
57. Foti, M.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1994, 116, 9440.
58. Boettcher, J. W.; Drago, R. S. J. Phys. Chem. 1974, 78, 429-431.
59. Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T. J. Am. Chem. Soc. 2002, 124, 11142-11147.
60. Huynh, M. H. V.; Meyer, T. J.; White, P. S. J. Am. Chem. Soc. 1999, 121, 4530-4531.
61. Huynh, M.-H. V.; White, P. S.; Meyer, T. J. Angew. Chem., Int. Ed. 2000, 39, 4101-4104.
62. Huynh, M. H. V.; Meyer, T. J. Angew. Chem., Int. Ed. 2002, 41, 1395-1398.
63. Mahoney, L. R.; DaRooge, M. A. J. Am. Chem. Soc. 1975, 97, 4722-4731.
64. Denisov, E. T. Kinet. Catal. 1994, 35, 671-691.
65. Denisov, E. T. Russ. Chem. Rev. 1997, 66, 859-876.
66. McMahon, R. J. Science 2003, 299, 833-834 and references therein.