Synthesis and characterization of formyl and hydroxymethyl complexes derived from isomeric cations: Cis-Ru(N-N)(η2-tpy)(CO)22+ 2PF6- (N-N = 2,2′-bipyridine, 4,4′-dimethyl-2,2′-bipyridine; tpy = 2,2′:6′,2″-terpyridine)

Organometallics

Volumn 20, Issue 23, 2001, Pages 4956-4964

  Gibson, Dorothy H ^a   Andino, Jose G ^a   Bhamidi, Srinivas ^a   Sleadd, Bradley A ^a   Mashuta, Mark S ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIPYRIDINE; FORMYL; GLYOXYLIC ACID; HYDROXYMETHYL COMPLEXES; ISOMERIC CATIONS; SODIUM BOROHYDRIDE; THERMOLYSIS;

CHARACTERIZATION; DERIVATIVES; ISOMERS; MOLECULAR STRUCTURE; ORGANIC ACIDS; POSITIVE IONS; PYROLYSIS; REDUCTION; RUTHENIUM COMPOUNDS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ORGANOMETALLICS;

EID: 0035851958     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010520i     Document Type: Article

References (64)

1. (a) Hawecker, J.; Lehn, J. M.; Ziessel, R. J. Chem. Soc., Chem. Commun. 1983, 536.
2. (b) Sullivan, B. P.; Bolinger, C. M.; Conrad, D.; Vining, T. J.; Meyer, T. J. J. Chem. Soc., Chem. Commun. 1985, 1414.
3. (c) Sullivan, B. P.; Conrad, D.; Meyer, T. J. Inorg. Chem. 1985, 24, 3640.
4. (d) Hawecker, J.; Lehn, J.-M.; Ziessel, R. Helv. Chim. Acta 1986, 69, 1990.
5. (e) Ishida, H.; Tanaka, K.; Tanaka, T. Organometallics 1987, 6, 181.
6. (f) Bruce, M. R. M.; Megehee, E.; Sullivan, B. P.; Thorp, H.; O'Toole, T. R.; Downard, A.; Meyer, T. J. Organometallics 1988, 7, 238.
7. (g) Sullivan, B. P.; Bruce, M. R. M.; O'Toole, T. R.; Bolinger, C. M.; Megehee, E.; Thorp, H.; Meyer, T. J. In Catalytic Activation of Carbon Dioxide; Ayers, W. M., Ed.; ACS Symp. Ser. 363; American Chemical Society: Washington, DC, 1988; Chapter 6.
8. (h) Ziessel, R. In Catalysis by Metal Complexes: Photosensitization and Photocatalysis Using Inorganic and Organometallic Compounds; Kalyanasundaram, K., Grätzel, M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1993; p 217.
9. (i) Christensen, P.; Hammett, A.; Muir, A. V. G.; Timney, J. H. J. Chem. Soc., Dalton Trans. 1992, 1455.
10. (j) Yoshida, T.; Tsutsumida, K.; Teratani, S.; Yasufuku, K.; Kaneko, M. J. Chem. Soc., Chem. Commun. 1993, 631.
11. (k) Stor, G. J.; Hartl, F.; van Outersterp, J. W. M.; Stufkens, D. J. Organometallics 1995, 14, 115.
12. (l) Johnson, F. P. A.; George, M. W.; Hartl, F.; Turner, J. J. Organometallics 1996, 15, 3374.
13. (m) Klein, A.; Vogler, C.; Kaim, W. Organometallics 1996, 15, 236.
14. (n) Sutin, N.; Creutz, C.; Fujita, E. Comments Inorg. Chem. 1997, 19, 67.
15. (o) Scheiring, T.; Klein, A.; Kaim, W. J. Chem. Soc., Perkin Trans. 2 1997, 2569.
16. Sende, J. A. R.; Arana, C. R.; Hernandez, L.; Potts, K. T.; Keshevarz, K. M.; Abruna, H. D. Inorg. Chem. 1995, 34, 3339.
17. Nagao, H.; Mizukawa, T.; Tanaka, K. Inorg. Chem. 1994, 33, 3415.
18. Hori, Y.; Murata, A.; Takahashi, R.; Suzuki, S. J. Chem. Soc., Chem. Commun. 1988, 17.
19. Tanaka, K.; Kushi, Y.; Tsuge, K.; Toyohara, K.; Nishioka, T. Isobe, K. Inorg. Chem. 1998, 37, 120.
20. Kusama, H.; Okabe, K.; Sayama, K. Arakawa, H. Catal. Today 1996, 28, 261.
21. (a) Tanaka, H.; Nagao, H.; Peng, S.-M.; Tanaka, K. Organometallics 1992, 11, 1450.
22. (b) Tanaka, H.; Tzeng, B.-C.; Nagao, H.; Peng, S.-M.; Tanaka, K. Inorg. Chem. 1993, 32, 1508.
23. (c) Toyohara, K.; Nagao, H., Muzukawa, T.; Tanaka, K. Inorg. Chem. 1995, 34, 5399.
24. (d) Toyohara, K.; Tsuge, K.; Tanaka, K. Organometallics 1995, 14, 5099.
25. (e) Toyohara, K.; Nagao, H.; Adachi, T.; Yoshida, T.; Tanaka, K. Chem. Lett. 1996, 27.
26. (f) Nakajima, H.; Tsuge, K.; Toyohara, K.; Tanaka, K. J. Organomet. Chem. 1998, 569, 61.
27. (g) Haukka, M.; Kiviaho, J.; Ahlgren, M.; Pakkanen, T. A. Organometallics 1995, 14, 825.
28. (h) Gibson, D. H.; Ding, Y.; Sleadd, B. A.; Franco, J. O.; Richardson, J. F.; Mashuta, M. S. J. Am. Chem. Soc. 1996, 118, 11984.
29. (i) Gibson, D. H.; Sleadd, B. A.; Mashuta, M. S.; Richardson, J. F. Organometallics 1997, 16, 4421.
30. (j) Gibson, D. H.; Yin, X. J. Am. Chem. Soc. 1998, 120, 11200.
31. (k) Gibson, D. H.; Sleadd, B. A.; Yin, X.; Vij, A. Organometallics 1998, 17, 2689.
32. (l) Gibson, D. H.; Ding, Y.; Andino, J. G.; Mashuta, M. S.; Richardson, J. F. Organometallics 1998, 17, 5178.
33. (m) Gibson, D. H.; Sleadd, B. A.; Mashuta, M. S.; Richardson, J. F. Acta Crystallogr. 1998, C54, 1584.
34. (n) Gibson, D. H.; Sleadd, B. A.; Vij, A. J. Chem. Crystallog. 1999, 29, 619.
35. (o) Gibson, D. H.; Yin, X. J. Chem. Soc., Chem. Commun. 1999, 1411.
36. (a) Darensbourg, D. J.; Fisher, M. B.; Schmidt, R. E., Jr.; Baldwin, B. J. J. Am. Chem. Soc. 1981, 103, 1297.
37. (b) Darensbourg, D. J.; Kudaroski, R. J. Am. Chem. Soc. 1984, 106, 3672.
38. (c) Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057.
39. (a) Ford, P. C.; Rokicki, A. Adv. Organomet. Chem. 1988, 28, 139.
40. (b) Torrent, M.; Solá, M.; Frenking, G. Chem. Rev. 2000, 100, 439.
41. Cation 2b was prepared previously (Thomas, N. C.; Fischer, J. J. Coord. Chem. 1990, 21, 119); the protonated form of the phenanthroline analogue was characterized by X-ray crystallography.
42. Cl; see: Civetello, E. R.; Dragovitch, P. S.; Karpishin, T. B.; Novick, S. G.; Bierach, G.; O'Connell, J. F.; Westmoreland, T. D. Inorg. Chem. 1993, 32, 237. In that context, compounds 2a,b (and 5a,b) are desribed as linkage isomers.
43. (a) Berke, H.; Huttner, G.; Weiler, G.; Zsolnai, L. J. Organomet. Chem. 1981, 219, 353.
44. (b) Vaughn, G. A.; Gladysz, J. A. J. Am. Chem. Soc. 1986, 108, 1473.
45. (c) There is one further hydroxymethyl complex that inserts CO, but the reaction pathway may involve radical species. See: van Voorhees, S. L.; Wayland, B. B. Organometallics 1985, 4, 1887.
46. (a) Sheridan, J. B.; Johnson, J. R.; Handwerker, B. M.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1988, 7, 2404.
47. (b) Geoffroy, G. L.; Sheridan, J. B.; Bussmer, S. L.; Kelley, C. Pure Appl. Chem. 1989, 61, 1723.
48. Groen, J. H.; de Zwart, A.; Vlaar, M. J. M.; Ernsting, J. M.; van Leeuwen, P. W. N. M.; Vrieze, K.; Kooijman, H.; Smeets, W. J. J.; Spek, A. L.; Budzelaar, P. H. M.; Xiang, Q.; Thummel, R. P. Eur. J. Inorg. Chem. 1998, 1129.
49. (a) Abel, E. W.; Dimitrou, V. S.; Long, N. J.; Orrell, K. G.; Osbourne, A. G.; Sik, V.; Hursthouse, M. B.; Mazid, M. A. J. Chem. Soc., Dalton Trans. 1993, 291.
50. 4 were unsuccessful, possibly due to hydrolyzed reagent.
51. Because of the pendant pyridine ligand in these complexes, each compound exists as a pair of enantiomers. The structure of only one enantiomer has been solved in each case.
52. We have not been able to find precedent for the naming of compounds such as these which would specify the position of the pendant pyridine in 2a,b or 5a,b. We suggest the prefix cis,syn-N for 2a (or 5a) to indicate that the pendant pyridine is near to coordinated nitrogen; similarly, we suggest the prefix cis,syn-C to specify that the pendant pyridine in 2b (or 5b) is near to coordinated CO.
53. Recently, a mixture of the two cations has been synthesized but could not be separated into the components: Fletcher, N. C.; Keene, F. R. J. Chem. Soc., Dalton Trans. 1998, 2293.
54. (a) Gladysz, J. A. Adv. Organomet. Chem. 1982, 20, 1.
55. (b) Gibson, D. H.; Mandall, S. K.; Owens, K.; Richardson, J. F. Organometallics 1987, 6, 2624.
56. (c) Gibson, D. H.; Owens, K.; Mandal, S. K.; Franco, J. O.; Sattich, W. E. Organometallics 1989, 8, 498.
57. Thorn, D. L.; Tulip, T. H. Organometallics 1982, 1, 1580.
58. See ref 7i and references therein.
59. Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.; Giacovazzo, C.; Gualiardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435.
60. teXsan: Single-Crystal Structure Analysis Software, Version 1.6; Molecular Structure Corp.: The Woodlands, TX 77381, 1993.
61. Sheldrick, G. M. SHELXS-90, Acta Crystallogr. 1990, A46, 467.
62. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997.
63. SHELXTL 5.10, Program Library for Structure Solution and Molecular Graphics; Bruker Analytical X-ray Systems: Madison, WI, 1997.
64. Farrugia, L. J. ORTEP-3 for Windows, J. Appl. Crystallogr. 1997, 30, 565.