Polycarbon Ligand Chemistry: Electronic Interactions between a Mononuclear Ruthenium Fragment and a Cobalt-Carbon Cluster Core

Organometallics

Volumn 18, Issue 19, 1999, Pages 3885-3897

  Low, Paul J ^a   Rousseau, Roger ^a   Lam, Pikka ^a   Udachin, Konstantin A ^a   Enright, Gary D ^a   Tse, John S ^a   Wayner, Danial D M ^a   Carty, Arthur J ^a,b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000539728     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990290w     Document Type: Article

References (136)

1. (a) Ward, M. D. Chem. Soc. Rev. 1995, 121.
2. (b) Ward, M. Chem. Ind. 1997, 640.
3. (c) Grosshenny, V.; Harriman, A.; Hissler, M.; Ziessel, R. Platinum Met. Rev. 1996, 40, 26.
4. (d) Petty, M. C.; Bryce, M. R.; Bloor, D. Introduction to Molecular Electronics; Oxford University Press: New York, 1995.
5. (a) Posselt, D.; Badur, W.; Steiner M.; Baumgarten, M. Synth. Met. 1993, 55, 3299.
6. (b) Hmyene, M.; Yassar, A.; Escorne, M.; Perchon-Guégan, A.; Garnier, F. Adv. Mater. 1994, 6, 564.
7. (c) Cargill Thompson, A. M. W.; Gatteschi, D.; McCleverty, J. A.; Navas, J. A.; Rentschler, E.; Ward, M. D. Inorg. Chem. 1996, 35, 2701.
8. (d) Ung, V. A.; Cargill Thompson, A. M. W.; Bardwell, D. A.; Gatteschi, D.; Jeffery, J. C.; McCleverty, J. A.; Totti, F.; Ward, M. D. Inorg. Chem. 1997, 36, 3447.
9. (a) Carter, F. L. In Electronic Devices II; Marcel Dekker: New York, 1987.
10. (b) Goppel, W., Zeigler, C., Eds. Nanostructures Based on Molecular Materials; VCH: Weinheim, 1992.
11. (c) Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, 1995.
12. (d) Tour, J. M. Chem. Rev. 1996, 96, 537.
13. (a) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
14. (b) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
15. (c) Whittal, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291.
16. (a) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier Science Publishers: New York, 1988.
17. (b) March, J. Advanced Organic Chemistry, 3rd ed.; Plenum; New York, 1985.
18. (a) Anderson, H. L. Inorg. Chem. 1994, 33, 972.
19. (b) Arnold, D. P.; Nitschinsk, L. Tetrahedron 1992, 48, 8781.
20. (c) Arnold, D. P.; Heath, G. A.; James, D. A. New J. Chem. 1998, 12, 1377.
21. (d) Anderson, H. L. Tetrahedron Lett. 1992, 33, 1101.
22. (a) Rosenblum, M.; Brawn, N.; Papenmeier, J.; Applebaum, M. J. Organomet. Chem. 1966, 6, 173.
23. (b) Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. Organometallics 1995, 14, 4808.
24. (a) Nast, R. Coord. Chem. Rev. 1982, 47, 89.
25. (b) Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 79.
26. (a) Sappa, E.; Tiripicchio, A.; Braunstein, P. Chem. Rev. 1983, 83, 203.
27. (b) Sappa, E.; Tiripicchio, A.; Braunstein, P. Coord. Chem. Rev. 1985, 65, 219.
28. (c) Bruce, M. I. J. Organomet. Chem. 1985, 257, 417.
29. Woitellier, S.; Launay, J. P.; Joachim, C. Chem. Phys. 1989, 131, 481.
30. Taylor, P. N.; Wylie, A. P.; Huuskonen, J.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 986.
31. (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775.
32. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414.
33. (c) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655.
34. (a) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129.
35. (b) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477.
36. Bruce, M. I.; Denisovich, L. I.; Low, P. J.; Peregudova, S. M.; Ustynyuk, N. A. Mendeleev Commun. 1996, 200.
37. (a) Osella, D.; Rossetti, R.; Nervi, C.; Ravera, M.; Moretta, M.; Fiedler, J.; Popsisil, L.; Samuel, E. Organometallics 1997, 16, 695.
38. (b) Osella, D.; Milone, L.; Nervi, C.; Ravera, M. Eur. J. Inorg. Chem. 1998, 1473.
39. (a) Duffy, N.; McAdam, C. J.; Nervi, C.; Osella, D.; Ravera, M.; Robinson, B. H.; Simpson, J. Inorg. Chim. Acta 1996, 247, 99.
40. (b) McAdam, C. J.; Duffy, N. W.; Robinson, B. H.; Simpson, J. Organometallics 1996, 15, 3935.
41. (c) Worth, G. H.; Robinson, B. H.; Simpson, J. Organometallics 1992, 11, 3863.
42. (d) Dellaca, R. J.; Penfold, B. R.; Robinson, B. H.; Robinson, W. T.; Spencer, J. L. Inorg. Chem. 1970, 9, 2204.
43. (a) Frapper, G.; Kertesz, M. Inorg. Chem. 1993, 32, 732.
44. (b) Belanzoni, P.; Re, N.; Sgamellotti, A.; Floriani, C. J. Chem. Soc., Dalton Trans. 1998, 1825.
45. (c) Re, N.; Sgamellotti, A.; Floriani, C. J. Chem. Soc., Dalton Trans. 1998, 2521.
46. (d) Bruce, M. I.; Halet, J.-F.; Kahlal, S.; Low, P. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem., in press.
47. (a) Lemoine, P. Coord. Chem. Rev. 1982, 47, 56.
48. (b) Lemoine, P. Coord. Chem. Rev. 1988, 83, 169.
49. (c) Geiger, W. E. Prog. Inorg. Chem. 1985, 33, 275.
50. (d) Drake, S. R. Polyhedron 1990, 9, 455.
51. Andres, R. P.; Bielefeld, J. D.; Henderson, J. I.; Janes, D. B.; Kolagunta, V. R.; Kubiak, C. P.; Mahoney, W. J.; Osifchin, R. G. Science 1996, 273, 1690.
52. (a) Goh, C.; Holm, R. H. Inorg. Chim. Acta 1998, 270, 46.
53. (b) Noodleman, L.; Peng, C. Y.; Case, D. A.; Mouesca, J.-M. Coord. Chem. Rev. 1995, 144, 199.
54. (c) Golbeck, J. H. Biochim. Biophys. Acta 1987, 895, 167.
55. (d) Cammack, R., Sykes, A. G., Eds. Iron-Sulfur Proteins; Academic Press: San Diego, 1992, and references therein.
56. Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882, and references therein.
57. Osella, D.; Gambino, O.; Nevi, C.; Ravera, M.; Bertolino, D. Inorg. Chim. Acta 1993, 206, 155.
58. Miguel, D.; Moreno, M.; Pérez, J.; Riera, V.; Churchill, D. G.; Churchill, M. R.; Janik, T. S. J. Am. Chem. Soc. 1998, 120, 417.
59. (a) Bruce, M. I.; Snow, M. R.; Tiekink, E. R. T.; Williams, M. L. J. Chem. Soc., Chem. Commun. 1986, 701.
60. (b) Adams, C. J.; Bruce, M. I.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, C9.
61. (c) Blenkiron, P.; Enright, G. D.; Low, P. J.; Corrigan, J. F.; Taylor, N. J.; Chi, Y.; Saillard, J.-Y.; Carty, A. J. Organometallics 1998, 17, 2447.
62. Adams, C. J.; Bruce, M. I.; Horn, E.; Skelton, B. W.; Tiekink, E. R. T.; White, A. H. J. Chem. Soc., Dalton Trans. 1993, 3299.
63. (a) Lewis, J.; Lin, B.; Khan, M. S.; Al-Mandhury, M. R. A.; Raithby, P. R. J. Organomet. Chem. 1994, 484, 161.
64. (b) Duffy, N.; McAdam, J.; Nervi, C.; Osella, D.; Ravera, M.; Robinson, B.; Simpson, J. Inorg. Chim. Acta 1996, 247, 99.
65. (c) Bruce, M. I.; Low, P. J.; Werth, A.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1996, 1551.
66. (a) Magnus, P.; Becker, D. P. J. Chem. Soc., Chem. Commun. 1985, 640.
67. (b) Agh-Atabay, N. M.; Lindsell, W. E.; Preston, P. N.; Tomb, P. J.; Lloyd, A. D.; Raugel-Rojo, R.; Spruce, G.; Wherrett, B. S. J. Mater. Chem. 1992, 2, 1241.
68. (c) Lindsell, W. E.; Preston, P. N.; Tomb, P. J. J. Organomet. Chem. 1992, 439, 201.
69. (d) Matsumoto, T.; Kotani, S.; Shiina, K.; Sonogashira, K. Appl. Organomet. Chem. 1993, 7, 613.
70. Diederich, F.; Rubin, Y.; Chapman, O. L.; Goroff, N. S. Helv. Chim. Acta 1994, 77, 1441.
71. (a) Bruce, M. I.; Ke, M.; Low, P. J. Chem. Commun. 1996, 2405.
72. (b) Bruce, M. I.; Skelton, B. W.; White, A. H.; Zaitseva, N. N. J. Chem. Soc., Dalton Trans. 1996, 3151.
73. Akita, M.; Sakura, A.; Moro-oka, Y. Chem. Commun. 1999, 101.
74. Akita, M.; Chung, M.-C.; Terada, M.; Miyauti, M.; Tanaka, M.; Moro-oka, Y. J. Organomet. Chem. 1998, 565, 49.
75. Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922.
76. Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033.
77. Coat, F.; Guillevic, M.-A.; Toupet, L.; Paul, F.; Lapinte, C. Organometallics 1997, 16, 5988.
78. (a) Low, P. J.; Enright, G. D.; Carty, A. J. J. Organomet. Chem. 1998, 565, 279.
79. (b) Low, P. J.; Udachin, K. A.; Enright, G. D.; Carty, A. J. J. Organomet. Chem. 1999, 578, 103.
80. (a) Davies, S. G. In Organotransition Metal Chemistry: Applications to Organic Synthesis; Pergamon: Oxford, 1986; pp 86-90.
81. (b) Kunz, H.; Waldmann, H. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 6, pp 692-693.
82. (a) Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A. tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; pp 233-246.
83. (b) Shore, N. E. Chem. Rev. 1988, 88, 1081.
84. (c) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064.
85. (d) Shore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, pp 703-739.
86. (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207.
87. (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, pp 685-702.
88. (c) Vizniowski, C. S.; Green, J. R.; Breen, T. L.; Dalacu, A. V. J. Org. Chem. 1995, 60, 7496.
89. 2(alkyne) complexes see: Dickson, R. S.; Fraser, P. J. Adv. Organomet. Chem. 1974, 12, 323.
90. (a) Lomprey, J. R.; Selegue, J. P. Organometallics 1993, 12, 616.
91. (b) Weyland, T.; Lapinte, C.; Frapper, G.; Calhorda, M. J.; Halet, J.-F.; Toupet, L. Organometallics 1997, 16, 2024.
92. (c) Bruce, M. I.; Hall, B. C.; Kelly, B. D.; Low, P. J. Unpublished results.
93. Bruce, M. I.; Low, P. J.; Werth, A.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1996, 1551.
94. (a) Bruce, M. I.; Humphrey, M. G.; Snow, M. R.; Tiekink, E. R. T. J. Organomet. Chem. 1986, 314, 213.
95. (b) Whittall, I. R.; Humphrey, M. G.; Persoons, A.; Houbrechts, S. Organometallics 1996, 15, 1935.
96. (a) Osella, D.; Fiedler, J. Organometallics 1992, 11, 3875.
97. (b) Duffy, N. W.; McAdam, C. J.; Robinson, B. H.; Simpson, J. J. Organomet. Chem. 1998, 565, 19.
98. Arewgoda, C. M.; Robinson, B. H.; Simpson, J. J. Am. Chem. Soc. 1983, 105, 1893.
99. (a) Connelly, N. G.; Gamasa, M. P.; Gimeno, J.; Lapinte, C.; Lastra, E.; Maher, J. P.; Le Narvor, N.; Rieger, A. L.; Rieger, P. H. J. Chem. Soc., Dalton Trans. 1993, 2575.
100. (b) Adams, J. S.; Bitcon, C.; Brown, J. R.; Collison, D.; Cunningham, M.; Whiteley, M. W. J. Chem. Soc., Dalton Trans. 1987, 3049.
101. (c) Beddoes, R. L.; Bitcon, C.; Whiteley, M. W. J. Organomet. Chem. 1991, 402, 85.
102. (d) Whittall, I. R.; Humphrey, M. G.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Organometallics 1995, 14, 3970.
103. (a) Beddoes, R. L.; Bitcon, C.; Ricalton, A.; Whiteley, M. W. J. Organomet. Chem. 1989, 367, C21.
104. (b) Bitcon, C.; Whiteley, M. W. J. Organomet. Chem. 1987, 336, 385.
105. (a) Hoffman, D. F.; Hoffmann, R.; Fisel, C. R. J. Am. Chem. Soc. 1982, 82, 3858.
106. For further discussion see for example: (b) Thron, D. L.; Hoffmann, B. Inorg. Chem. 1978, 17, 126.
107. (c) DeKock, R. L.; Lubben, T. V.; Hwang, J.; Fehlner, T. P. Inorg. Chem. 1981, 20, 1627.
108. (d) Baert, F.; Guelzim, A.; Poblet, J. M.; Wiest, R.; Demuynck, J.; Bunard, M. Inorg. Chem. 1986, 25, 1830.
109. (e) Pepermans, H.; Hoogzand, C.; Geerlings, P. J. Organomet. Chem. 1986, 306, 395.
110. (f) Halet, J.-F.; Saillard, J.-Y. J. Organomet. Chem. 1987, 327, 365.
111. (g) Yuan, P.; Don, M.-J.; Richmond, M. G.; Schwartz, M. Inorg. Chem. 1992, 31, 3491.
112. McGrady, J. E.; Lovell, T.; Stranger, R.; Humphrey, M. G. Organometallics 1997, 16, 4004.
113. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 5397.
114. (a) Silvi, B.; Savin, A. Nature (London) 1994, 371, 683.
115. (b) Savin, A.; Jepsen, O.; Flad, J.; Andersen, O. K.; Preu, H.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 187.
116. (c) Savin, A.; Nesper, R.; Wengert, S.; Fössler, T. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1808.
117. (d) Savin, A.; Becke, A. D.; Flad, J.; Nesper, R.; Preuss, H.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1991, 30, 409.
118. (e) Marx, D.; Savin, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2077.
119. Rubin, Y.; Lin, S. S.; Knobler, C. B.; Anthony, J.; Doldi, A. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 6943.
120. Chia, L. S.; Cullen, W. R. Inorg. Chem. 1975, 14, 482.
121. Bruce, M. I.; Hameister, C.; Swincer, A. G.; Wallis, R. C. Inorg. Synth. 1990, 28, 270.
122. (a) Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
123. (b) Sheldrick, G. M. Acta Crystallogr. 1993, A49 (Suppl.), C53.
124. (a) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
125. (b) Jones, R. O.; Gunnarsson, O. Rev. Mod. Phys. 1989, 61, 689.
126. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
127. 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.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
128. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270, 299.
129. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
130. Anderson, W. P.; Edwards, W. D.; Zerner, M. C. Inorg. Chem. 1985, 25, 2728.
131. Hyperchem, Release 4.5 for Silicon Graphics workstations; Hypercube Inc.: Aug 1995.
132. (a) Kresse, G.; Hafner, J. Phys. Rev. B 1993, 47, 55; 1994, 49, 14251.
133. (a) Kresse, G.; Hafner, J. Phys. Rev. B 1993, 47, 55; 1994, 49, 14251.
134. (b) Kresse, G.; Furthmuller, J. Comput. Mater. Sci. 1995, 6, 15. Kresse, G.; Furthmuller, J. Phys. Rev. B 1996, 54, 11169.
135. (b) Kresse, G.; Furthmuller, J. Comput. Mater. Sci. 1995, 6, 15. Kresse, G.; Furthmuller, J. Phys. Rev. B 1996, 54, 11169.
136. Vanderbelt, D. Phys. Rev. B 1990, 41, 7892. The pseudopotentials used were those taken from the database provided with the VASP program.