Reduction of water to H2 by diorganopalladium(II) complexes of tris(pyrazol-1-yl)borate: Ab-initio theoretical study of the mechanism

Organometallics

Volumn 16, Issue 24, 1997, Pages 5331-5341

  Milet, Anne ^a   Dedieu, Alain ^a   Canty, Allan J ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF TASMANIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001718973     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9702338     Document Type: Article

References (96)

1. (a) Monaghan, P. K.; Puddephatt, R. J. Inorg. Chim. Acta 1982, 65, L59.
2. (b) Monaghan, P. K; Puddephatt, R. J. Organometallics 1984, 3, 444.
3. (c) Appleton, T. G.; Hall, J. R.; Neale, D. W.; Williams, M. A. J. Organomet. Chem. 1984, 276, C73.
4. (a) Canty, A. J.; Honeyman, R. T.; Roberts, A. S.; Traill, P. R.; Colton, R.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1994, 471, C8.
5. (b) Canty, A. J.; Fritsche, S. D.; Jin, H.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1995, 490, C18.
6. (c) Canty, A. J.; Fritsche, S. D.; Jin, H.; Honeyman, R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1996, 510, 281.
7. (d) Canty, A. J.; Fritsche, S. D.; Jin, H.; Patel, J.; Skelton, B. W.; White, A. H. Organometallics 1997, 16, 2175.
8. Canty, A. J.; van Koten, G. Acc. Chem. Res. 1995, 28, 406.
9. (a) Canty, A. J.; Jin, H.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1995, 503, C16.
10. (b) Canty, A. J.; Jin, H.; Roberts, A. S.; Skelton, B. W. Organometallics 1996, 15, 5713.
11. Canty, A. J.; Dedieu, A.; Jin, H.; Milet, A.; Richmond, M. K. Organometallics 1996, 15, 2845.
12. Canty, A. J.; Jin, H.; Roberts, A. S.; Skelton, B. W.; Traill, P. R.; White, A. H. Organometallics 1995, 14, 199.
13. Part of this work has been presented previously, see: Canty, A. J. Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA, April 13-17, 1997; American Chemical Society: Washington, DC, 1997; 7-ORGN.
14. (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.; Reploge, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, revision E.2.; Gaussian, Inc.: Pittsburgh, PA, 1992.
15. (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.; Petersson, 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.; Reploge, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian 94, revision B.2.; Gaussian, Inc.: Pittsburgh, PA, 1995.
16. (c) The calculations used five functions with true d character.
17. Canty, A. J.; Dedieu, A.; Jin, H.; Milet, A.; Skelton, B. W.; Trofimenko, S.; White, A. H. To be published
18. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
19. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
20. (a) Huzinaga, S. Technical Report; University of Alberta: Edmonton, 1971.
21. (b) Huzinaga, S. J. Chem. Phys. 1965, 42, 1293.
22. (a) Milet, A.; Dedieu, A. Theoret. Chim. Acta 1995, 92, 361.
23. (b) Milet, A. Ph.D. Thesis, Université Louis Pasteur, Strasbourg, France, 1997.
24. (c) Dedieu, A.; Kapteijn, G. Unpublished results.
25. Xantheas, S. S. J. Am. Chem. Soc. 1995, 117, 10373 and references therein.
26. Siegbahn, P. E. M. J. Comput. Chem. 1996, 17, 1099.
27. -1, thus also in good agreement with the experimental value.
28. Tuñón, I.; Rinaldi, D.; Ruiz-López, M. F.; Rivail, J. L. J. Phys. Chem. 1995, 99, 3798.
29. -, -75.5693.
30. Canty, A. J.; Minchin, N. J.; Engelhardt, L. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1986, 645.
31. Rush, P. E.; Oliver, J. D. J. Chem. Soc., Chem. Commun. 1974, 996.
32. Oliver, J. D.; Rice, N. C. Inorg. Chem. 1976, 15, 2741.
33. (a) Granell, J.; Sales, J.; Declercq, J. P.; Germain, G.; Miratvitlles, C.; Solans, X. J. Chem. Soc., Dalton Trans. 1983, 2441.
34. (b) Granell, J.; Sainz, D.; Sales, J.; Solans, X.; Font-Altaba, M. J. Chem. Soc., Dalton Trans. 1986, 1785.
35. (c) Villanueva, L. A.; Abboud, K.; Boncella, J. M. Organometallics 1991, 10, 2969.
36. Bucher, U. E.; Currao, A.; Nesper, R.; Rüegger, H.; Venanzi, L. M.; Younger, E. Inorg. Chem. 1995, 34, 66.
37. Wehman-Ooyevaar, I. C. M.; Grove, D. M.; de Vaal, P.; Dedieu, A.; van Koten, G, Inorg. Chem. 1992, 31, 5484.
38. (a) De Felice, V.; De Renzi, A.; Panunzi, A.; Tesauro, D. J. Organomet. Chem. 1995, 488, C13.
39. (b) Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966.
40. (c) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371.
41. (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
42. O'Reilly, A. A.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1996, 118, 5684.
43. (a) Albinati, A.; Anklin, C. G.; Ganazzoli, F.; Ruegg, H.; Pregosin, P. S. Inorg. Chem. 1987, 26, 503.
44. (b) Blake, A. J.; Holder, A. J.; Roberts, Y. V.; Schroder, M. J. Chem. Soc., Chem. Commun. 1993, 260.
45. Brammer, L.; Zhao, D.; Lapido, F. T.; Braddock-Wilking, J. Acta Crystallogr. 1995, B51, 632.
46. (a) Albinati, A.; Arz, C.; Pregosin, P. S. Inorg. Chem. 1987, 26, 508.
47. (b) Brammer, L.; Charnock, J. M.; Goggin, P. L.; Goodfellow, R. J.; Orpen, G.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1991, 1789.
48. (c) Albinati, A.; Lianza, F.; Muller, B.; Pregosin, P. S. Inorg. Chim. Acta 1993, 208, 119.
49. (d) Albinati, A.; Lianza, F.; Pregosin, P. S.; Muller, B. Inorg. Chem. 1994, 33, 2522.
50. Wehman-Ooyevaar, I. C. M.; Grove, D. M.; Kooijman, H.; van der Sluis, P.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1992, 114, 9916.
51. NMR evidence for the presence of organo(hydrido)palladium-(IV) species as components of a mixture has been presented, see: Vedernikov, A. N.; Kuramshin, A. I.; Solomonov, B. N. J. Chem. Soc., Chem. Commun. 1994, 121.
52. (a) Byers, P. K.; Canty, A. J.; Minchin, N. J.; Patrick, J. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1985, 1183.
53. (b) Ball, R. G.; Ghosh, C. K.; Hoyano, J. K.; McMaster, A. D.; Graham, W. A. G. J. Chem. Soc., Chem. Commun. 1989, 341.
54. (c) Rheingold, A. L.; Haggerty, B. S.; Trofimenko, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1983.
55. 12
56. (b) SCRF calculations carried out at the MP2 level on the same systems show that the energy difference decreases on increasing the polarity of the solvent (Gaudé, S.; Dedieu, A. Unpublished results)
57. Jones, W. D.; Hessel, E. T. Inorg. Chem. 1991, 30, 778.
58. 2O. Attempts that used a cyclic transition state involving more than one molecule of water as a hypothesis, i.e. cyclic transition states involving two or three water molecules, were also unsuccessful.
59. Milet, A.; Dedieu, A.; Kapteijn, G.; van Koten, G. Inorg. Chem. 1897, 36, 3223.
60. -1,
61. -1.
62. (a) Milstein, D.; Calabrese, J. C.; Williams, I. D. J. Am. Chem. Soc. 1986, 108, 6387.
63. (b) Stevens, R. C.; Bau, R.; Milstein, D.; Blum, O.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1990, 1429.
64. (a) Canty, A. J. Acc. Chem. Res. 1992, 11, 83.
65. (b) Canty, A. J. in Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: London, 1995.
66. 2.
67. 35
68. Aullón, G.; Alvarez, S. Inorg. Chem. 1996, 35, 3137.
69. Pearson, R. G. J. Am. Chem. Soc. 1986, 108, 6109.
70. Meot-Ner, M. J. Am. Chem. Soc. 1986, 108, 6189.
71. 45 An ellipsoidal cavity based on the van der Waals surface was taken, and the multipole expansion used in the formulation of the electrostatic free energy was truncated after l = 6. Bulk dielectric constants of 20.7 and 78.5 were chosen for acetone and water, respectively.
72. (a) See, for instance, ref 16 and references therein,
73. (b) Rinaldi, D.; Pappalardo, R. R. SCRFPAC; QCPE, Indiana University: Bloomington, IN, 1992; program no. 622.
74. -1.
75. -1.
76. 2O and the nitrogen atom of hydrazone.
77. (a) Lee, J. C., Jr.; Rheingold, A. L.; Muller, B.; Pregosin, P. S.; Crabtree, R. H. J. Chem. Soc., Chem. Commun. 1994, 1021.
78. (b) Lee, J. C., Jr.; Peris, E.; Rheingold, A. L.; Crabtree, R. H. J. Am. Chem. Soc. 1994, 116, 11014.
79. (c) Peris, E.; Lee, J. C., Jr.; Crabtree, R. H; J. Chem. Soc., Chem. Commun. 1994, 2573.
80. (d) Peris, E.; Lee, J. C., Jr.; Rambo, J.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 1995, 777, 3485.
81. (f) Patel, B. P.; Yao, W.; Yap, G. P. A.; Rheingold, A. L.; Crabtree, R. H. J. Chem. Soc., Chem. Commun. 1996, 991.
82. (a) Park, S.; Ramachandran, R.; Lough, A. J.; Morris, R. H. J. Chem. Soc., Chem. Commun. 1994, 2201.
83. (b) Lough, A. J.; Park, S.; Ramachandran, R.; Morris, R. H. J. Am. Chem. Soc. 1994, 116, 8356.
84. (c) Xu, W.; Lough, A. J.; Morris, R. H.; Inorg. Chem. 1996, 35, 1549.
85. Liu, Q.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 10108.
86. For intermolecular M-H⋯H-N hydrogen bonding, see: (a) Wessel, J.; Lee, J. C.; Peris, E.; Yap, G. P. A.; Fortin, J. B.; Ricci, J. S.; Sini, G.; Albinati, A.; Koetzle, T. F.; Eisenstein, O.; Rheingold, A. L.; Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2507. (b) Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. F. Acc. Chem. Res. 1996, 29, 348.
87. For intermolecular M-H⋯H-N hydrogen bonding, see: (a) Wessel, J.; Lee, J. C.; Peris, E.; Yap, G. P. A.; Fortin, J. B.; Ricci, J. S.; Sini, G.; Albinati, A.; Koetzle, T. F.; Eisenstein, O.; Rheingold, A. L.; Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2507. (b) Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. F. Acc. Chem. Res. 1996, 29, 348.
88. For intermolecular M-H⋯H-O hydrogen bonding, see: (a) Shubina, E. S.; Belkova, N. V.; Krylov, A. N.; Vorontsov, E. V.; Epstein, L M.; Gusev, D. G.; Niedermann, M.; Berke, H. J. Am. Chem. Soc. 1996, 118, 1105. (b) Belkova, N. V.; Shubina, E. S.; Ionidis, A. V.; Epstein, L. M.; Jacobsen, H.; Messmer, A.; Berke, H. Inorg. Chem. 1997, 36, 1522.
89. For intermolecular M-H⋯H-O hydrogen bonding, see: (a) Shubina, E. S.; Belkova, N. V.; Krylov, A. N.; Vorontsov, E. V.; Epstein, L M.; Gusev, D. G.; Niedermann, M.; Berke, H. J. Am. Chem. Soc. 1996, 118, 1105. (b) Belkova, N. V.; Shubina, E. S.; Ionidis, A. V.; Epstein, L. M.; Jacobsen, H.; Messmer, A.; Berke, H. Inorg. Chem. 1997, 36, 1522.
90. 49d
91. 12b
92. 49d
93. 2 and to the simultaneous association of the pyrazole group.
94. Aye, K. T.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D.; Watson, A. A. Organometallics 1989, 8, 1518.
95. - has been reported after the initial submission of this paper, see: Ayllón, J. A.; Gervaux, C.; Sabo-Etienne, S.; Chaudret, B. Organometallics 1997, 16, 2000.
96. 12b