Neutral paddlewheel diruthenium complexes with tetracarboxylates of large π-conjugated substituents: Facile one-pot synthesis, crystal structures, and electrochemical studies

Inorganic Chemistry

Volumn 43, Issue 20, 2004, Pages 6464-6472

  Furukawa, Shuhei ^a   Kitagawa, Susumu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOIC ACID; 9 ANTHROIC ACID; ANTHRACENE; AROMATIC COMPOUND; BENZOIC ACID; CARBOXYLIC ACID DERIVATIVE; NAPHTHYL GROUP; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONJUGATE; CRYSTAL STRUCTURE; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; EXTRACTION; GAS CHROMATOGRAPHY; GEOMETRY; MASS SPECTROMETRY; MEASUREMENT; OXIDATION; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

CARBOXYLIC ACIDS; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; RUTHENIUM;

EID: 4644344342     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0493752     Document Type: Article

References (72)

1. Cotton, F. A.; Walton, R. A. Multiple Bonds between Metal Atoms, 2nd ed.; Clarendon Press: Oxford, 1993.
2. (a) Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759.
3. (b) Cotton, F. A.; Lin, C.; Murillo, C. A. Proc. Nat. Acad. Sci. 2002, 99, 4810.
4. (a) Cotton, F. A.; Daniels, L. M.; Lin, C.; Murillo, C. A. J. Am. Chem. Soc. 1999, 121, 4538.
5. (b) Cotton, F. A.; Donahue, J. P.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 1234.
6. (c) Cotton, F. A.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 478.
7. (d) Cotton, F. A.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 575.
8. (e) Cotton, F. A.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 472.
9. (f) Bursten, B. E.; Chisholm, M. H.; Clark, R. J. H.; Firth, S.; Hadad, C. M.; Wilson, P. J.; Woodward, P. M.; Zaleski, J. M. J. Am. Chem. Soc. 2002, 124, 12244.
10. (g) Bursten, B. E.; Chisholm, M. H.; Clark, R. J. H.; Firth, S.; Hadad, C. M.; MacIntosh, A. M.; Wilson, P. J.; Woodward, P. M.; Zaleski, J. M. J. Am. Chem. Soc. 2002, 124, 3050.
11. (h) Chisholm, M. H.; Pate, B. D.; Wilson, P. J.; Zaleski, J. M. Chem. Commun. 2002, 1084.
12. (i) Chisholm, M. H.; Wilson, P. J.; Woodward, P. M. Chem. Commun. 2002, 566.
13. (a) Cotton, F. A.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 5886.
14. (b) Cotton, F. A.; Lin, C.; Murillo, C. A. Chem. Commun. 2001, 11.
15. (c) Cotton, F. A.; Lin, C.; Murillo, C. A. J. Chem. Soc., Dalton Trans. 2001, 499.
16. (d) Bonar-Law, R. P.; McGrath, T. D.; Singh, N.; Bickley, J. F.; Steiner, A. Chem. Commun. 1999, 2457.
17. (e) Bonar-Law, R. P.; Bickley, J. F.; Femoni, C.; Steiner, A. J. Chem. Soc., Dalton Trans. 2000, 4244.
18. (f) Bickley, J. F.; Bonar-Law, R. P.; Femoni, C.; MacLean, E. J.; Steiner, A.; Teat, S. J. J. Chem. Soc., Dalton Trans. 2000, 4025.
19. (g) Bonar-Law, R. P.; McGrath, T. D.; Bickley, J. F.; Femoni, C.; Steiner, A. Inorg. Chem. Commun. 2001, 4, 16.
20. Aquino, M. A. S. Coord. Chem. Rev. 1998, 170, 141.
21. Jiménez-Aparicio, R.; Urbanos, F. A.; Arrieta, J. M. Inorg. Chem. 2001, 40, 613.
22. (a) Cotton, F. A.; Kim, Y.; Ren, T. Inorg. Chem. 1992, 31, 2723.
23. (b) Cotton, F. A.; Kim, Y.; Ren, T. Inorg. Chem. 1992, 31, 2608.
24. (c) Cotton, F. A.; Kim, Y.; Ren, T. Polyhedron 1993, 12, 607.
25. (d) Handa, M.; Sayama, Y.; Mikuriya, M.; Nukada, R.; Hiromitsu, I.; Kasuga, K. Chem. Lett. 1996, 201.
26. (e) Handa, M.; Sayama, Y.; Mikuriya, M.; Nukada, R.; Hiromitsu, I.; Kasuga, K. Bull. Chem. Soc. Jpn. 1998, 71, 119.
27. (f) Sayama, Y.; Handa, M.; Mikuriya, M.; Hiromitsu, I.; Kasuga, K. Chem. Lett. 1998, 777.
28. (g) Barral, M. C.; Jiménez-Aparicio, R.; Pérez-Quintanilla, D.; Priego, J. L.; Royer, E. C.; Torres, M. R.; Urbanos, F. A. Inorg. Chem. 2000, 39, 65.
29. (h) Miyasaka, H.; Clérac, R.; Campos-Fernández, C. S.; Dunbar, K. R. Inorg. Chem. 2001, 40, 1663.
30. (i) Sayama, Y.; Handa, M.; Mikuriya, M.; Hiromitsu, I.; Kasuga, K. Bull. Chem. Soc. Jpn. 2003, 76, 769.
31. (j) Beck, E. J.; Drysdale, K. D.; Thompson, L. K.; Li, L.; Murphy, C. A.; Aquino, M. A. S. Inorg. Chim. Acta 1998, 279, 121.
32. (k) Yoshioka, D.; Mikuriya, M.; Handa, M. Chem. Lett. 2002, 1044.
33. (l) Liao, Y.; Shum, W. W.; Miller, J. S. J. Am. Chem. Soc. 2002, 124, 9336.
34. Rose, D.; Wilkinson, G. J. Chem. Soc. A 1970, 1791.
35. Lindsay, A. J.; Tooze, R. P.; Motevalli, M.; Hursthouse, M. B.; Wilkinson, G. J. Chem. Soc., Chem. Commun. 1984, 1383.
36. Lindsay, A. J.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 2321.
37. Lindsay, A. J.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 2723.
38. (a) Miyasaka, H.; Campos-Fernández, C. S.; Clérac, R.; Dunbar, K. R. Angew. Chem., Int. Ed. 2000, 39, 3831.
39. (b) Miyasaka, H.; Clérac, R.; Campos-Fernández, C. S.; Dunbar, K. R. J. Chem. Soc., Dalton Trans. 2001, 858.
40. (c) Angariidis, P.; Berry, J. F.; Cotton, F. A.; Lei, P.; Lin, C.; Murillo, C. A.; Villagrán, D. Inorg. Chem. Commun. 2004, 7, 9
41. Compound 1 is not structurally characterized but has already been synthesized.
42. Urbanos, F. A.; Barral, M. C.; Jiménez-Aparicio, R. Polyhedron 1988, 7, 2597.
43. Crystal Structure Analysis Package; Molecular Structure Corporation: The Woodlands, TX, 1985 and 1992.
44. Mitchell, R. W.; Spencer, A.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1973, 846.
45. Bino, A.; Cotton, F. A.; Felthouse, T. R. Inorg. Chem. 1979, 18, 2599.
46. (a) Cotton, F. A.; Miskowski, V. M.; Zhong, B. J. Am. Chem. Soc. 1989, 111, 6177.
47. (b) Cotton, F. A.; Labella, L.; Shang, M. Inorg. Chim. Acta 1992, 197, 149.
48. (c) Barral, M. C.; Jiménez-Aparicio, R.; Priego, J. L.; Royer, E. C.; Urbanos, F. A.; Amador, U. Inorg. Chim. Acta 1998, 279, 30.
49. (a) Sakakibara, T.; Kotobuki, J.; Dogomori, Y. Chem. Lett. 1977, 25.
50. (b) Sakakibara, T.; Dogomori, Y.; Tsuzuki, Y. Bull. Chem. Soc. Jpn. 1979, 52, 3592.
51. Chisholm, M. H.; Christou, G.; Folting, K.; Huffman, J. C.; James, C. A.; Samuels, J. A.; Wesemann, J. L.; Woodruff, W. H. Inorg. Chem. 1996, 35, 3643.
52. 2].
53. Marsh, R. E.; Schomaker, V. Inorg. Chem. 1981, 20, 299.
54. Wang, Z.-Q.; Lu, S.-W.; Guo, H.-F.; Hu, N.-H.; Liu, Y.-S. Polyhedron 1991, 10, 2341.
55. Fitzgerald, L. J.; Gerkin, R. E. Acta Crystallogr. 1997, C53, 71.
56. Wolcan, E.; Torchia, G.; Tocho, J.; Piro, O. E.; Julianrena, P.; Ruiz, G.; Féliz, M. R. J. Chem. Soc., Dalton Trans. 2002, 2194.
57. Das, K.; Kadish, K. M.; Bear, J. L. Inorg. Chem. 1978, 17, 930.
58. Ren, T. Coord. Chem. Rev. 1998, 175, 43.
59. (a) Lin, C.; Protasiewicz, J. D.; Smith, E. T.; Ren, T. J. Chem. Soc., Chem. Commun. 1995, 2257.
60. (b) Lin, C.; Protasiewicz, J. D.; Smith, E. T.; Ren, T. Inorg. Chem. 1996, 35, 6422.
61. Lin, C.; Protasiewicz, J. D.; Ren, T. Inorg. Chem. 1996, 35, 7455.
62. Lin, C.; Ren, T.; Valente, E. J.; Zubkowski, J. D.; Smith, E. T. Chem. Lett. 1997, 753.
63. Ren, T.; Lin, C.; Valente, E. J.; Zubkowski, J. D. Inorg. Chim. Acta 2000, 297, 283.
64. Kadish, K. M.; Wang, L.-L.; Thuriere, A.; Van Caemelbecke, E.; Bear, J. L. Inorg. Chem. 2003, 42, 834.
65. Miyasaka, H.; Izawa, T.; Sugiura, K.; Yamashita, M. Inorg. Chem. 2003, 42, 7683.
66. Newman, M. S. Steric Effects in Organic Chemistry; John Wiley & Sons: New York, 1956.
67. Hammett, L. P. Physical Organic Chemistry; 2nd ed.; McGraw-Hill: New York, 1970.
68. Zuman, P. Substituent Effects in Organic Polarography; Plenum Press: New York, 1967.
69. - is calculated from electrochemical measurements of these aromatic polycyclic systems bound to various electroactive groups. The value of the reactivity constant, ρ, estimated from eq 4 can be used in the informative discussion of reactions for those calculated from the Taft constant and the Hammett constant.
70. - were carried out with less satisfactory results, which clearly indicates the absence of a dominant resonance contribution from the substituents.28 This is because the phenyl group has rotational freedom with respect to the first coordination sphere of the dimetal core, which eliminates any significant contribution through conjugation.
71. 2 centers through the conjugation is muted but not lost. In the case of our compounds, the definite information on the structure in solution has not been investigated; however, it seems reasonable to suppose that this obstruction of the rotation would allow the significant contribution through π-conjugation even though the planes are not flat in a manner similar to that of the dimer of dimer compound.
72. Byrnes, M. J.; Chisholm, M. H.; Dye, D. F.; Hadad, C. M.; Pate, B. D.; Wilson, P. J.; Zaleski, J. M. J. Chem. Soc., Dalton Trans. 2004, 523.