A reassessment of the bond dissociation energies of peroxides. An ab initio study

Journal of the American Chemical Society

Volumn 118, Issue 50, 1996, Pages 12758-12765

  Bach, Robert D ^a   Ayala, Philippe Y ^b   Schlegel, H B ^b  

^a UNIVERSITY OF DELAWARE   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEROXIDE;

ARTICLE; MOLECULAR DYNAMICS; THEORY; THERMODYNAMICS;

EID: 0030464437     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961838i     Document Type: Article

References (68)

1. (a) Cremer, D. In The Chemistry of Functional Groups Peroxides; Patai, S., Ed.; John Wiley & Sons: New York, 1983; p 1.
2. (b) Baldwin, A. C. Ibid.; p 97.
3. (c) Bouillon, G.; Lick, C.; Shank, K. Ibid.; p 279.
4. (d) Oae, S.; Fujimori, K. Ibid.; p 585.
5. (e) Kerr, J. A. Chem. Rev. 1966, 66, 465.
6. (f) Fujimori, K. In Organic Peroxides; Ando, W., Ed.; John Wiley & Sons; New York, 1992; p 319.
7. (a) Benson, S. W.; Shaw, R. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 1.
8. (b) Barker, J. R.; Benson, S. W.; Golden, D. M. Int. J. Chem. Kinel. 1977, 9, 31.
9. (c) Nangla, P. S.; Benson, S. W. J. Phys. Chem. 1979, 83, 1138.
10. (d) Benson, S. W. J. Chem. Phys. 1964, 40, 1007.
11. (e) Benson, S. W.; O'Neal, H. E. Kinetic Data on Gas Phase Unimolecular Reactions; NSRDS-NBS21; U. S. Government Printing Office: Washington, DC, 1970.
12. (f) Benson, S. W.; Cruickshank, F. R.; Golden, D. M.; Haugen, G. R.; O'Neal, H. E.; Rodgers, A. S.; Shaw, R.; Walsh, R. Chem. Rev. 1969, 69, 279.
13. 2 as oxidants; Strukul, G., Ed.; Series: Catalysis by Metal Complexes; Reidel-Kluwer: Dordrecht, The Netherlands, 1992; Chapter 3.
14. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59.
15. (a) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A, 3rd ed.; Plenum Press: New York, 1990; p 284.
16. (b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; p 367.
17. (a) Swern, D. Organic Reactions; John Wiley & Sons: New York, Vol. VII, p 378.
18. (b) DiFuria, F.; Modena, G. Pure Appl. Chem. 1982, 54, 1853.
19. (c) Dryuk, V. G. Russ. Chem. Rev. 1985, 54, 986.
20. (d) Swern, D. Organic Peroxides; Wiley-Interscience: New York, 1971; Vol. II, pp 73-74.
21. (a) For a discussion of solvent-assisted proton transfer in alkyl hydrogen peroxides see: Dankleff, M. A. P.; Ruggero, C.; Edwards, J. O.; Pyun, H. Y. J. Am. Chem. Soc. 1968, 90, 3209.
22. (b) Curci, R.; DiPrete, R. A.; Edwards, J. O.; Modena, G. J. Org. Chem. 1970, 35, 740.
23. (a) Bach, R. D.; Su, M.-D.; Schlegel, H. B. J. Am. Chem. Soc. 1994, 116, 5379.
24. (b) Ibid. 1991, 113, 6001.
25. (c) Bach, R. D.; Owensby, A.; González, C.; Schlegel, H. B. Ibid. 1991, 113, 2338.
26. (d) Bach, R. D.; Andrés, J. L.; Owensby, A.; Schlegel, H. B. Ibid. 1992, 114, 7207.
27. (a) For a discussion of homolytic dissociation energies employing generalized valence bond (GVB) in connection with localized spin density correlations (LSDC), see: Kraka, E. Chem. Phys. 1992, 161, 149.
28. e (corrected for zero point energy) is 55.1 kcal/mol. (b) Luo, X.; Fleming, P. R.; Rizzo, T. R. J. Chem. Phys. 1992, 5659, 96.
29. (c) Chase, M. W.; Davies, C. A.; Downey, J. R.; Frurip, D. J.; McDonald, R. A.; Syverud, A. N. JANAF Thermodynamical Tables. J. Phys. Chem. Ref. Data, Supp. 1 1985, 14.
30. (a) Bach, R. D.; Winter, J. E.; McDouall, J. J. W. J. Am. Chem. Soc. 1995, 117, 8586.
31. (b) Bach, R. D.; Andrés, J. L.; Gonzalez, C.; Fox, G. L.; Estévez, C. M.; Winter, J. E.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc., submitted.
32. (c) Bach, R. D.; Winter, J. E.; Estévez, C. M. J. Am. Chem. Soc., submitted.
33. (a) Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
34. (b) Curtiss, L. A.; Raghavachari, K.; Pople, J. A. Ibid. 1993, 98, 1293.
35. (c) Stevens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Chem. Phys. 1994, 98, 11623.
36. (d) Bauschlicher, C. W.; Partridge, H. J. Chem. Phys. 1995, 103, 1788.
37. (e) B3LYP appears to be better than other DFT methods for calculating bond dissociation energies for oxygen-containing compounds: Jursic, B. S.; Martin, R. M. Int. J. Quantum. Chem. 1996, 59, 495.
38. (a) Petersson, G. A.; Tensfeldt, T. G.; Montgomery, J. A. J. Chem. Phys. 1991, 94, 6091.
39. (b) Montgomery, J. A., Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1994, 101, 5900.
40. (c) Ochterski, J. W.; Petersson, G. A.; Wiberg, K. B. J. Am. Chem. Soc. 1995, 117, 11299.
41. (d) Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1996, 104, 2598.
42. 12c
43. (b) GAUSSIAN 94: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc., Pittsburgh, PA, 1995.
44. (c) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
45. (d) The methyl groups in peroxyacetic acid and diacyl peroxide are effectively free rotors. Since these methyl groups are also free rotors in the product acetyloxyl radical, their effect on the O-O bond dissociation energy cancels.
46. Huber, K. P.; Herzberg, G. Molecular Spectra and Molecular Structure; Van Nostrand Reinhold: New York, 1979; Vol. 4.
47. Handy, N. C.; Pople, J. A.; Head-Gordon, M.; Raghavachari, K.; Trucks, G. W. Chem. Phys. Lett. 1989, 164, 185.
48. (a) McLean, A. D.; Lengsfield, B. H., III; Pacansky, J.; Elliger, Y. J. Chem. Phys. 1985, 83, 3567.
49. (b) Rauk, A.; Dake, Y.; Borowski, P.; Roos, B. Chem. Phys. 1995, 197, 73.
50. (c) Blahous, C. P.; Yates, B. F.; Xie, Y.; Schaefer, H. F. J. Chem. Phys. 1990, 93, 8105.
51. Hart, H. Acc. Chem. Res. 1971, 4, 337.
52. (a) Jaffe, L.; Prosen, E. J.; Szwarc, M. J. Chem. Phys. 1957, 27, 416.
53. (b) Rembaum, A.; Szwarc, M. J. Am. Chem. Soc. 1954, 76, 5975.
54. Shine, H. J.; Hoffman, D. M. J. Am. Chem. Soc. 1961, 83, 2782.
55. (a) Goldstein, M. J.; Judson, H. A. J. Am. Chem. Soc. 1970, 92, 4119.
56. (b) Goldstein, M. J.; Haiby, W. A. J. Am. Chem. Soc. 1974, 96, 7358.
57. Frequencies calculated at a higher level of theory than B3LYP/6-31G* would be needed to characterize these structures accurately.
58. Ervin, K.; Ho, J.; Lineberger, W. C. J. Phys. Chem. 1988, 92, 5405.
59. Clemmer, D. E.; Armentrout, P. B. J. Phys. Chem. 1992, 97, 2451.
60. (a) Lias, S. G.; Bartness, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas Phase Ion and Neutral Thermochemistry. J. Phys. Chem. Ref. Data, Suppl. 1 1988, 17.
61. (b) H.; Hamilton, T. P.; Tsai, J. M.; van der Woerd, M.; Harrison, J. G.; Jablonsky, M. J.; Beckman, J. S.; Koppenol, W. H. Unpublished results.
62. Holmes, J. L.; Lossing, F. P.; Meyer, P. M. J. Am. Chem. Soc. 1991, 113, 9723.
63. (a) Dupuis, M.; Murray, C.; Davidson, E. R. J. Am. Chem. Soc. 1991, 113, 9756.
64. (b) Hrovat, D. A.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 1072.
65. (c) Borden, W. T.; Davidson, E. R. Acc. Chem. Res. 1996, 29, 67.
66. (a) Catoire, V.; Lesclaux, R.; Schneider, W. F.; Wallington, T. J. J. Phys. Chem., in press.
67. (b) Schneider, W. F.; Nance, B. I.; Wallington, T. J. J. Am. Chem. Soc. 1995, 117, 478.
68. (c) Schneider, W. F.; Wallington, T. J. J. Phys. Chem. 1993, 97, 12783.