Mechanism of the participation of water in the decomposition of hydrogen trioxide (HOOOH). A theoretical study

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2470-2472

  Koller, Jože ^a   Plesničar, Božo ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

WATER;

ARTICLE; ENERGY TRANSFER; THEORY; THERMODYNAMICS;

EID: 0029892432     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9503387     Document Type: Article

References (41)

1. Plesničar, B.; Cerkovnik, J.; Koller, J.; Kovač, F. J. Am. Chem. Soc. 1991, 113, 4946.
2. (b) For a review on polyoxides, see Plesničar, B. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; pp 479-533.
3. (a) Cerkovnik, J.; Plesničar, B. J. Am. Chem. Soc. 1993, 115, 12169.
4. (b) Cerkovnik, J.; Plesničar, B. 12th IUPAC Conference on Physical Organic Chemistry. Padova, Italy, 1994; Book of Abstracts, p 238; In preparation.
5. Mozurkevich, M. J. Phys. Chem. 1986, 90, 2216. DeMore, W. B. J. Phys. Chem. 1982, 86, 121. Dransfeld, P.; Wagner, H. Gg. Z. Naturforsch. 1987, 42a, 471. Wennberg, P. O.; Cohen, R. C.; Stimpfle, R. M.; Koplow, J. P.; Anderson, J. G.; Salawitch, R. J.; Fahey, D. W.; Woodbridge, E. L.; Keim, E. R.; Gao. R. S.; Webster, C. R.; May, R. D.; Toohey, D. W.; Avallone, L. M.; Proffitt, M. H.; Loewenstein, M.; Podolske, J. R.; Chan, K. R.; Wofsy, S. C. Science 1994, 266, 398.
6. Mozurkevich, M. J. Phys. Chem. 1986, 90, 2216. DeMore, W. B. J. Phys. Chem. 1982, 86, 121. Dransfeld, P.; Wagner, H. Gg. Z. Naturforsch. 1987, 42a, 471. Wennberg, P. O.; Cohen, R. C.; Stimpfle, R. M.; Koplow, J. P.; Anderson, J. G.; Salawitch, R. J.; Fahey, D. W.; Woodbridge, E. L.; Keim, E. R.; Gao. R. S.; Webster, C. R.; May, R. D.; Toohey, D. W.; Avallone, L. M.; Proffitt, M. H.; Loewenstein, M.; Podolske, J. R.; Chan, K. R.; Wofsy, S. C. Science 1994, 266, 398.
7. Mozurkevich, M. J. Phys. Chem. 1986, 90, 2216. DeMore, W. B. J. Phys. Chem. 1982, 86, 121. Dransfeld, P.; Wagner, H. Gg. Z. Naturforsch. 1987, 42a, 471. Wennberg, P. O.; Cohen, R. C.; Stimpfle, R. M.; Koplow, J. P.; Anderson, J. G.; Salawitch, R. J.; Fahey, D. W.; Woodbridge, E. L.; Keim, E. R.; Gao. R. S.; Webster, C. R.; May, R. D.; Toohey, D. W.; Avallone, L. M.; Proffitt, M. H.; Loewenstein, M.; Podolske, J. R.; Chan, K. R.; Wofsy, S. C. Science 1994, 266, 398.
8. Mozurkevich, M. J. Phys. Chem. 1986, 90, 2216. DeMore, W. B. J. Phys. Chem. 1982, 86, 121. Dransfeld, P.; Wagner, H. Gg. Z. Naturforsch. 1987, 42a, 471. Wennberg, P. O.; Cohen, R. C.; Stimpfle, R. M.; Koplow, J. P.; Anderson, J. G.; Salawitch, R. J.; Fahey, D. W.; Woodbridge, E. L.; Keim, E. R.; Gao. R. S.; Webster, C. R.; May, R. D.; Toohey, D. W.; Avallone, L. M.; Proffitt, M. H.; Loewenstein, M.; Podolske, J. R.; Chan, K. R.; Wofsy, S. C. Science 1994, 266, 398.
9. Sawyer, D. T. Oxygen Chemistry; Oxford University Press: Oxford, 1991. Deby, C. La Recherche 1991, 228, 57.
10. Sawyer, D. T. Oxygen Chemistry; Oxford University Press: Oxford, 1991. Deby, C. La Recherche 1991, 228, 57.
11. Gonzalez, C.; Theisen, J.; Zhu, L.; Schlegel, H. B.; Hase, W. L.; Kaiser, E. W. J. Phys. Chem. 1991, 95, 6784; 1992, 96, 1767.
12. Gonzalez, C.; Theisen, J.; Zhu, L.; Schlegel, H. B.; Hase, W. L.; Kaiser, E. W. J. Phys. Chem. 1991, 95, 6784; 1992, 96, 1767.
13. 1 in HF. This trend was observed also by using the 6-31++G* basis set.
14. 1H NMR) of hydrogen trioxide, generated by the low-temperature ozonation of hydrazobenzene. This system provided relatively the highest yields of HOOOH without the interfering presence of organic hydrotrioxides (ROOOH), and allowed the use of a variety of solvents for kinetic measurements.
15. 17O 187 ppm).
16. 1/2 = 17 s in 0.027 M acid at O °C) with the activation energy of 16.5 kcal/mol at pH 2. Bielski, B. H. J.; Schwartz, H. A. J. Phys. Chem. 1968, 72, 3836.
17. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, L. R.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. GAUSSIAN 92; Gaussian Inc.: Pittsburgh, PA, 1992.
18. (b) Frisch, M. J.; Trucks, G. W.; Schlegel. H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; 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.; Gonzale, C.; Pople, J. A. GAUSSIAN 94, Revision B.3; Gaussian, Inc.; Pittsburgh, PA, 1995.
19. (c) Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968. Krishan, R.; Binkley, J. S.; Seegar, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W. S.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
20. (c) Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968. Krishan, R.; Binkley, J. S.; Seegar, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W. S.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
21. (c) Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968. Krishan, R.; Binkley, J. S.; Seegar, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W. S.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
22. (d) Becke, A. D. Phys. Rev. A 1988, 38, 3098. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
23. (d) Becke, A. D. Phys. Rev. A 1988, 38, 3098. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
24. (e) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Chem. 1980, 58, 1200.
25. (a) For a pioneering modern ab initio study of HOOOH, see: Cremer, D. J. Chem. Phys. 1978, 69, 4456. Cremer, D. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York. 1983; Chapter 1.
26. (a) For a pioneering modern ab initio study of HOOOH, see: Cremer, D. J. Chem. Phys. 1978, 69, 4456. Cremer, D. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York. 1983; Chapter 1.
27. (b) See also: Jackels, C. F.; Phillips, D. J. J. Chem. Phys, 1986, 84, 5013.
28. For theoretical studies of the modification of potential energy surfaces by solvation, see for example: Bosch, E.; Lluch, J. M.; Bertran, J. J. Am. Chem. Soc. 1990, 112, 3868 and references cited therein. Bach, R. D.; Owensby, A. L.; Gonzalez, C.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1991, 113, 6001. Morokuma, K.; Muguruma, C. J. Am. Chem. Soc. 1994, 116, 10316.
29. For theoretical studies of the modification of potential energy surfaces by solvation, see for example: Bosch, E.; Lluch, J. M.; Bertran, J. J. Am. Chem. Soc. 1990, 112, 3868 and references cited therein. Bach, R. D.; Owensby, A. L.; Gonzalez, C.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1991, 113, 6001. Morokuma, K.; Muguruma, C. J. Am. Chem. Soc. 1994, 116, 10316.
30. For theoretical studies of the modification of potential energy surfaces by solvation, see for example: Bosch, E.; Lluch, J. M.; Bertran, J. J. Am. Chem. Soc. 1990, 112, 3868 and references cited therein. Bach, R. D.; Owensby, A. L.; Gonzalez, C.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1991, 113, 6001. Morokuma, K.; Muguruma, C. J. Am. Chem. Soc. 1994, 116, 10316.
31. 4 bond which was somewhat longer in TS-2 than in HOOOH. The energy (6-31++G) of TS-2 was 22.6 kcal/ mol higher than that of the isolated reactants and 35.1 kcal/mol higher than that of the HOOOH-HOH complex. The corresponding 6-31++G*//6-31++G* values were much higher, i.e., 43.8 and 51.6 kcal/mol, respectively. (See supporting information.)
32. Nangia, P. S.; Benson, S. W. J. Am. Chem. Soc. 1980, 102, 3105. Pryor, W. A.; Ohto, N.; Church, D. F. J. Am. Chem. Soc. 1983, 105, 3614. Li. S.; Deslongchamps, P. Tetrahedron Lett. 1993, 34, 7759 and references therein.
33. Nangia, P. S.; Benson, S. W. J. Am. Chem. Soc. 1980, 102, 3105. Pryor, W. A.; Ohto, N.; Church, D. F. J. Am. Chem. Soc. 1983, 105, 3614. Li. S.; Deslongchamps, P. Tetrahedron Lett. 1993, 34, 7759 and references therein.
34. Nangia, P. S.; Benson, S. W. J. Am. Chem. Soc. 1980, 102, 3105. Pryor, W. A.; Ohto, N.; Church, D. F. J. Am. Chem. Soc. 1983, 105, 3614. Li. S.; Deslongchamps, P. Tetrahedron Lett. 1993, 34, 7759 and references therein.
35. ·: R(H-O) = 0.976 Å, E = -75.55717 au).
36. 2 = 82.1°. MP4/ /MP2/6-31++G*, E = -452.29031 au.
37. (a) Mo, O.; Yanez, M.; Rozas, I.; Elguero, J. Chem. Phys. Lett. 1994, 219, 45.
38. (b) Dobado, J. A.; Molina, J. M. J. Phys. Chem. 1994, 98, 1819.
39. -: R(H-O) = 0.979 Å, E = -75.59732 au.
40. 2) = 374.8 ± 0.7 kcal/mol. Bierbaum, V. M.; Schmitt, R. J.; DePuy, C. H.; Mead, R. D.; Schulz, P. A.; Lineberger, W. C. J. Am. Chem. Soc. 1981, 103, 6262.
41. ‡). It is interesting to mention that while one molecule of water served as a bifunctional catalyst (as in TS-2), the second water molecule only stabilized the TS-3 by forming two intermolecular hydrogen bonds with the partially formed "hydrotrioxide anion" part of the TS-3. (See supporting information.)