Model study of the acid-base proton-transfer reaction of the CIH⋯OH2 pair in low-polarity solvents

Journal of Physical Chemistry A

Volumn 105, Issue 12, 2001, Pages 2581-2590

  Thompson, Ward H ^a,c   Hynes, James T ^a,b  

^a UNIVERSITY OF COLORADO   (United States)

^b ECOLE NORMALE SUPÉRIEURE   (France)

^c UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646101485     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (81)

1. Ando, K.; Hynes, J. T. J. Phys. Chem. B 1997, 101, 10464-10478.
2. Ando, K.; Hynes, J. T. J. Mol. Liq. 1995, 64, 25-37.
3. (a) Gertner, B. J.; Hynes, J. T. Science 1996, 271, 1563.
4. (b) Gertner, B. J.; Hynes, J. T. Faraday Discuss. 1998, 110, 301.
5. Hanson, D. R.; Ravishankara, A. R. J. Phys. Chem. 1992, 96, 2682-2691.
6. Molina, M. J. The Chemistry of the Atmosphere: Its Impact on Global Change; IUPAC, Blackwell: Oxford, U.K., 1994; p 27.
7. Thibert, E; Dominé F. J. Phys. Chem. B 1997, 101, 3554.
8. Graham, J. D.; Roberts, J. T. J. Phys. Chem. 1994, 98, 5764.
9. Morris, J. R.; Behr, P.; Antman, M. D.; Ringeisen, B. R.; Splan, J.; Nathanson, G. M. J. Phys. Chem. A 2000, 104, 6738-6751.
10. Clary, D. C.; Wang, L. C. J. Chem. Soc., Faraday Trans. 1997, 93, 2763-2767.
11. Robertson, S. H.; Clary, D. C. Faraday Discuss. 1995, 100, 309-320.
12. Estrin, D. A.; Kohanoff, J.; Laria, D. H.; Weht, R. O.; Chem. Phys. Lett. 1997, 280, 280-286.
13. Allouche, A.; Couteurier-Tamburelli, I.; Chiavassa, T. J. Phys. Chem. B 2000, 104, 1497-1506.
14. Kroes, G. J. Comments At. Mol. Phys. 1999, 34, 259.
15. Laasonen, K. E.; Klein, M. L. J. Phys. Chem. A 1997, 101, 98.
16. Laasonen, K. E.; Klein M. L. J. Am. Chem. Soc. 1994, 116, 11620.
17. Balbuena, P. B.; Johnston, K. P.; Rossky, P. J. J. Phys. Chem. 1996, 100, 2716.
18. Marx, D.; Tuckerman, M. E.; Hutter. J.; Parrinello, M. Nature 1999, 397, 601.
19. Hynes, J. T. Nature 1999, 397, 565.
20. Schmitt, U. W.; Voth, G. A. J. Chem. Phys. 1999, 111, 9361-9381.
21. Schmitt, U. W.; Voth, G. A. Isr. J. Chem. 1999, 39, 483-492.
22. Hammes-Schiffer, S.; Tully, J. C. J. Chem. Phys. 1994, 101, 4567-4667.
23. Hammes-Schiffer, S.; Tully, J. C. J. Phys. Chem. 1995, 99, 5793-5797.
24. Hammes-Schiffer, S. J. Phys. Chem. A 1998, 102, 10443-10454.
25. Staib, A.; Borgis, D.; Hynes, J. T. J. Chem. Phys. 1995, 102, 2487-2505.
26. Borgis, D.; Hynes, J. T. J. Phys. Chem. 1996, 100, 1118-1128;
27. Borgis, D.; Hynes, J. T. Chem. Phys. 1993, 170, 315-346.
28. Borgis, D.; Hynes, J. T. J. Chem. Phys. 1991, 94, 3619-3628.
29. Borgis, D.; Lee, S.-Y.; Hynes, J. T. Chem. Phys. Lett. 1989, 162, 19-26.
30. Vuilleumier, R.; Borgis, D. J. Chem. Phys. 1999, 111, 4251-4266.
31. Vuilleumier, R.; Borgis, D. J. Phys. Chem. B 1998, 102, 4261-4264.
32. Azzouz, H.; Borgis, D. J. Mol. Liq. 1995, 63, 89-107.
33. Ando, K.; Hynes, J. T. Discuss. Faraday Soc. 1995, 102, 435-441.
34. Ando, K.; Hynes, J. T. J. Phys. Chem. A 1999, 103, 10398-10408.
35. Ando, K.; Hynes, J. T. Adv. Chem. Phys. 1999, 110, 381-430 and references therein.
36. Mulliken, R. S. J. Phys. Chem. 1952, 56, 801-822.
37. Mulliken, R. S. J. Chim. Phys. Phys.-Chim. Biol. 1964, 61, 20-36.
38. Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley-Interscience: New York, 1969.
39. Bratož, S. Adv. Quantum Chem. 1967, 3, 209-237.
40. Ratajczak, H. J. Phys. Chem. 1972, 76, 3000-3004; 3991-3992.
41. Zwilles, B. A.; Person, W. B. J. Chem: Phys. 1983, 79, 65.
42. Timoneda, J.; Hynes, J. T. J. Phys. Chem. 1991, 95, 10431-10442.
43. See also, Thompson, W. H.; Hynes, J. T. J. Am. Chem. Soc. 2000, 122, 6278-6286.
44. Borgis, D.; Tarjus, G.; Azzouz, H. J. Phys. Chem. 1992, 96, 3188-3191.
45. Borgis, D.; Tarjus, G.; Azzouz, H. J. Chem. Phys: 1992, 97, 390-400.
46. Warshel, A. J. Phys. Chem. 1982, 86, 2218;
47. Warshel, A. Computer Modeling of Chemical Reactions in Enzymes and Solutions; Wiley: New York, 1991.
48. It is clear that the bend coordinate of the hydrogen bond complex may play an important role in the energetics and dynamics of the PT reaction. However, for simplicity, this coordinate is frozen in the present study, and this aspect of the problem will be addressed in future work.
49. All ab initio calculations reported in this paper were carried out using Frisch, M. J.; Trucks, G, W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J,; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
50. OHw = 0.964 Å. The H-O-H angle in the water molecule is 106.0°, and the Cl-H-O angle is 178.5°.
51. Re, S.; Osamura, Y.; Suzuki, Y.; Schaefer, H. F., III. J. Chem. Phys. 1998, 109, 973-977.
52. Szczeñniak, M. M.; Scheiner, S.; Bouteiller, Y. J. Chem. Phys. 1984, 81, 5024-5030.
53. The Morse potential at small r typically is not as strongly repulsive as that found, for example, in ab initio calculations.
54. Roszak, S. Chem. Phys. Lett. 1996, 250, 187-191.
55. Press, W. H.; Flannery, B. P.; Teukolsky, S. A.; Vetterling, W. T. Numerical Recipes, The Art of Scientific Computing; Cambridge University Press: Cambridge, U.K., 1992.
56. Kim, H. J.; Hynes, J. T. J. Chem. Phys. 1992, 96, 5088.
57. Grasselli, J. G., Ritchey, W. M., Eds.; Atlas of Spectral Data and Physical Constants for Organic Compounds; The Chemical Rubber Company: Cleveland, OH, 1975.
58. One could equivalently use an energy gap coordinate (see, e.g., ref 17) to characterize a solvent coordinate. For the present purposes, the coordinate z is slightly preferable in that it gives a sense of the polarization state in the solvent via eq 12.
59. Colbert, D. T.; Miller, W. H. J. Chem. Phys. 1992, 96, 1982-1991.
60. Kiefer, P. M.; Hynes, J. T. Nonlinear Free Energy Relationships for Adiabatic Proton-Transfer Reactions in a Polar Environment; I. Fixed Proton Donor-Acceptor Distance and Nonlinear Free Energy Relationships for Adiabatic Proton-Transfer Reactions in a Polar Environment. II. Inclusion of Proton Donor-Acceptor Vibration; Manuscripts in preparation.
61. Kim, H. J.; Staib, A.; Hynes, J. T. In Ultrafast Reaction Dynamics at Atomic-Scale Resolution Femtochemistry and Femtobiology, Nobel Symposium 101; Sundstrom, V., Ed.; Imperial College Press: London, 1998.
62. Laage, D.; Thompson, W. H.; Hynes, J. T. Work in progress.
63. Cleland, W. W.; Kreevoy, M. M. Science 1994, 267, 1887.
64. Golubev, N. S.; Denisov, G. S.; Smirnov, S. N.; Shchepkin, D. N.; Limbach, H.-H. Z Phys. Chem. 1996, 196, 73-84.
65. Perrin, C.L.; Nielsen, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511-544.
66. 40 have examined the HCl and pyridine acid-base pair and find that under the conditions of their experiment it only exists in the ionized form of chloride ion and pyridinium. This is not inconsistent with the present results involving water, a much weaker base.
67. King, E. J. In Physical Chemistry of Organic Solvent Systems; Covington, A. K., Dickinson, T., Eds.; Plenum Press: New York, 1973; pp 331-388.
68. See, for example, Zumdahl, S. S.; Zumdahl, S. A. Chemistry; Houghton Mifflin: New York, 2000.
69. Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 4694-4701.
70. Anne, A.; Fraoua, S.; Grass, V.; Moiroux, J.; Savéant, J.-M. J. Am. Chem. Soc. 1998, 120, 2951-2958.
71. Marcus, R. A. Faraday Symp. Chem. Soc. 1975, 10, 60.
72. Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
73. Cohen, A. O.; Marcus, R. A. J. Phys. Chem. 1968, 72, 4249.
74. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224.
75. Agmon, N. Int. J. Chem. Kinet. 1981, 13, 333.
76. Pines, E.; Magnes, B.-Z.; Lang, M. J.; Fleming, G. R. Chem. Phys. Lett. 1997, 281, 413.
77. Kreevoy, M. M.; Konasewich, D. E. Adv. Chem. Phys. 1972, 21, 243.
78. Kreevoy, M. M.; Oh, S.-W. J. Am. Chem. Soc. 1973, 95, 4805.
79. Kresge, A. J. Acc. Chem. Res. 1975, 8, 354.
80. Kresge, A. J.; Silverman, D. N. Methods Enzymol. 1999, 308, 276.
81. Mulliken, R. S.; Rieke, C. A.; Orloff, D.; Orloff, H. J. Chem. Phys. 1949, 17, 1248.