Aqueous organometallic chemistry: Synthesis, structure, and reactivity of the water-soluble metal hydride CpRu(PTA) 2H

Organometallics

Volumn 23, Issue 22, 2004, Pages 5317-5323

  Frost, Brian J ^a   Mebi, Charles A ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC CHEMISTRY; PROTONATION; SOLID-STATE STRUCTURES; TRANSITION STATES;

CATALYSIS; CHEMICAL BONDS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; HYDRIDES; HYDROGENATION; ISOTOPES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; REACTION KINETICS; STOICHIOMETRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

ORGANOMETALLICS;

EID: 8344272116     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049501     Document Type: Article

References (62)

1. Dedieu, A., Ed. Transition Metal Hydrides; VCH: New York, 1992.
2. Peruzzini, M., Poli, R.; Eds. Recent Advances in Hydride Chemistry; Elsevier: New York, 2001.
3. Lemke, F. R.; Brammer, L. Organometallics 1995, 14, 3980-7.
4. Brammer, L.; Klooster, W. T.; Lemke, F. R. Organometallics 1996, 15, 1721-1727.
5. Smith, K. T.; Rømming, C.; Tilset, M. J. Am. Chem. Soc. 1993, 115, 8681-8689.
6. Bruce, M. I.; Butler, I. R.; Cullen, W. R.; Koutsantonis, G. A.; Snow, M. R.; Tiekink, E. R. T. Aust. J. Chem. 1988, 41, 963-969.
7. Litster, S. A.; Redhous, A. D.; Simpsons, S. J. Acta Crystallogr. 1992, C48, 1661-1663.
8. Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Janak, K. E. Organometallics 2003, 22, 4084-4089.
9. Daigle, D. J.; Pepperman, A. B. Jr.; Vail, S. L. J. Heterocycl. Chem. 1974, 11, 407-408.
10. Jó, F.; Laurenczy, G.; Karady, P.; Elek, J.; Nadasdi, L.; Roulet, R. Appl. Organomet. Chem. 2000, 14, 857-859.
11. Laurenczy, G.; Joó, F.; Nadasdi, L. Inorg. Chem. 2000, 39, 5083-5088.
12. Pruchnik, F. P.; Smolenski, P. Appl. Organomet. Chem. 1999, 13, 829-836.
13. Nadasdi, L.; Joó, F. Inorg. Chim. Acta 1999, 293, 218-222.
14. Pruchnik, F. P.; Smolenski, P.; Galdecka, E.; Galdecki, Z. New J. Chem. 1998, 22, 1395-1398.
15. Darensbourg, D. J.; Decuir, T. J.; Reibenspies, J. H. Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joó, F., Eds.; High Technology; Kluwer: Dordrecht, The Netherlands, 1995; pp 6180.
16. Darensbourg, D. J.; Stafford, N. W.; Joó, F.; Reibenspies, J. H. J. Organomet. Chem. 1995, 488, 99-108.
17. Pruchnik, F. P.; Smolenski, P.; Raksa, I. Polym. J. Chem. 1995, 69, 5-8.
18. Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joó, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963-3969.
19. Pruchnik, F. P.; Smolenski, P.; Wajda-Hermanowicz, K. J. Organomet. Chem. 1998, 570, 63-69.
20. Cermak, J.; Kvicalova, M.; Blechta, V. Collect. Czech. Chem. Commun. 1997, 62, 355-363.
21. Darensbourg, D. J.; Joó, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H.; Daigle, D. J. Inorg. Chem. 1994, 33, 200-208.
22. Darensbourg, D. J.; Joó, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990-1993.
23. Joó, F.; Nadasdi, L.; Benyei, A. Cs.; Darensbourg, D. J. J. Organomet. Chem. 1996, 522, 45-50.
24. Joó, F.; Laurenczy, G.; Nadasdi, L.; Elek, J. Chem. Commun. 1899, 971-972.
25. Benyei, A. Cs.; Lehel, S.; Joó, F. J. Mol. Catal. A. Chem. 1997, 116, 349-354.
26. Shafiq, F.; Szalda, D. J.; Creutz, C.; Bullock, R. M. Organometallies 2000, 19, 824-833.
27. Allardyce, C. S.; Dyson, P. J.; Ellis, D. J.; Heath, S. L. Chem. Commun. 2001, 1396-1397.
28. Dyson, P. J.; Ellig, D. J.; Henderson, W.; Laurenczy, G. Adv. Synth. Catal. 2003, 345, 216-221.
29. Allardyce, C. S.; Dyson, P. J.; Ellis, D. J.; Salter, P. A.; Scopelliti, R. J. Organomet. Chem. 2003, 668, 35-42.
30. Horvath, H.; Laurenczy, G.; Katho, A. J. Organomet. Chem. 2004, 659, 1036-1045.
31. Akbayeva, D. N.; Gonsalvi, L.; Oberhauser, W.; Peruzzini, M.; Vizza, F.; Brueggeller, P.; Romerosa, A.; Sava, G.; Bergamo, A. Chem. Commun. 2003, 264-265.
32. Daigle, D. J. Inorg. Synth. 1998, 32, 40-45.
33. Albers, M. O.; Liles, D. C.; Robinson, D. J.; Shaver, A.; Singleton, E.; Wiege, M. B.; Boeyens, J. C. A.; Levendis, D. C. Organometallics 1988, 5, 2321-2327.
34. Joslin, F. L.; Mague, J. T.; Roundhill, D. M. Organometallics 1991, 10, 521-524.
35. Wadt, W. E.; Hay, P. J. J. Chem. Phys. 1988, 82, 284-298.
36. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
37. Frisch, M. J.; Trucks. G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, O.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
38. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
39. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
40. Elian, M.; Hoffmann, R. Inorg. Chem. 1975, 14, 1058-1076.
41. Darensbourg, D. J.; Robertson, J. B.; Larkins, D. L.; Reibenspies, J. H. Inorg. Chem. 1999, 38, 2473-2481.
42. DeLerno, J. R.; Trefonas, L. M.; Darensbourg, M. Y.; Majeste, R. J. Inorg. Chem. 1978, 15, 816-819.
43. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
44. Drago, R. S. Physical Methods for Chemists, 2nd ed.; Saunders: Philadelphia, 1992.
45. Krimm, S. Infrared Spectroscopy and Molecular Structure; Elsevier: New York, 1963; Chapter 8.
46. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
47. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
48. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
49. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
50. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
51. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
52. See for example: (a) Kristfansdottir, S. S.; Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992. (b) Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 165-284. (c) Heinekey, D. M.; Oldham, W. J., Jr. Chem. Rev. 1993, 93, 913. (d) Chinn, M. S.; Heinekey, D. M. J. Am. Chem. Soc.1990, 112, 5168- 5175. (e) Bullock, R. M.; Song, J.-S.; Szalda, D. J. Organometallics 1996, 15, 2504-2616. (f) Ontko, A. C.; Houlis, J. F.; Schnabel, R. C.; Roddick, D. M.; Fong, T. P.; Lough, A. J.; Morris, R. H. Organometallics 1998, 17, 5467-5476. (g) Papish, E. T.; Magee, M. P.; Norton, J. R. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: New York, 2001; pp 39-74.
53. (a) Gaus, P. L.; Kao, S. C.; Darensbourg, M. Y.; Arndt, L. W. J. Am. Chem. Soc. 1984, 106, 4752-4755.
54. (b) Feracin, S.; Bürgi, T.; Bakhumtov, V.; Eremenko, I.; Vorontsov, E. V.; Vimenitis, A. B.; Berke, H. Organometallics 1994, 13, 4194-4202.
55. Normally, these reactions are viewed as proton transfers; however, Scheme 2 could also be viewed as a a bond metathesis.
56. Frost, B. J.; Mebi, C. A. Manuscript in preparation.
57. 1a.
58. Papish, E. T.; Rix, F. C.; Spetseris, N.; Norton, J. R.; Williams, R. D. J. Am. Chem. Soc. 2000, 122, 12235-12242.
59. Cheng, T.-Y.; Bullock, R. M. J. Am. Chem. Soc. 1999, 121, 3150-3155.
60. Edidin, R. T.; Sullivan, J. M.; Norton, J. R. J. Am. Chem. Soc. 1987, 109, 3945-3953.
61. Kuo, L. Y.; Weakley, T. J. R.; Awana, K.; Hsia, C. Organometallics 2001, 20, 4969-4972.
62. Paterniti, D. P.; Roman, P. J., Jr.; Atwood, J. D. Organometallics 1997, 16, 3371-3376.