Naked (C5Me5)2M cations (M = Sc, Ti, and V) and their fluoroarene complexes

Journal of the American Chemical Society

Volumn 127, Issue 41, 2005, Pages 14310-14319

  Bouwkamp, Marco W ^a   Budzelaar, Peter H M ^b,d   Gercama, Jeroen ^a   Del Hierro Morales, Isabel ^a   De Wolf, Jeanette ^a   Meetsma, Auke ^a   Troyanov, Sergei I ^c   Teuben, Jan H ^a   Hessen, Bart ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

^d UNIVERSITY OF MANITOBA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; ELECTRIC FIELDS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

DENSITY FUNCTIONAL THEORY (DFT); FLUOROBENZENE; METAL CENTER;

POSITIVE IONS;

ANION; CATION; FLUORINE DERIVATIVE; FLUOROBENZENE; METAL COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON; SCANDIUM; TITANIUM DERIVATIVE; VANADIUM DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; TITANIUM; TRANSITION ELEMENT; VANADIUM;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

CATIONS; CRYSTALLOGRAPHY, X-RAY; FLUOROBENZENES; LIGANDS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; SCANDIUM; TITANIUM; TRANSITION ELEMENTS; VANADIUM;

EID: 26844461511     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054544i     Document Type: Article

References (81)

1. Eggar, K. W.; Cocks, A. T. Helv. Chim. Acta 1973, 56, 1516.
2. The electronegativity of fluorine on the Pauling scale: 3.98. The Nature of the Chemical Bond and the Structure of Molecules and Crystals: an Introduction to Modern Structural Chemistry, Pauling, L., Ed.; Cornell University Press: Ithaca, NY, 1960.
3. Handbook of Chemistry and Physics, 80th edition; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1999-2000.
4. (a) Tsukahara, T.; Swenson, D. C.; Jordan, R. F. Organometallics 1997, 16, 3303.
5. (b) Brussee, E. A. C.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2000, 497.
6. (c) Saito, J.; Mitani, M.; Onda, M.; Mohri, J.I..; Ishii, S.-I.; Yoshida, Y.; Nakano, T.; Tanaka, H.; Matsugi, T.; Kojoh, S.I.; Kashiwa, N.; Fujita, T. Macromol. Rapid Commun. 2001, 22, 1072.
7. (d) Mitani, M.; Mohri, J. I.; Yoshida, Y.; Saito, J.; Ishii, S.; Tsuru, K.; Matsui, S.; Furuyama, R.; Nakano, T.; Tanaka, H.; Kojoh, S.-I.; Matsugi, T.; Kashiwa, N.; Fujita, T. J. Am. Chem. Soc. 2002, 124, 3327.
8. (e) Thornberry, M. P.; Reynolds, N. T.; Deck, P. A.; Fronczek, F. R.; Rheingold, A. L.; Liable-Sands, L. M. Organometallics 2004, 23, 1333.
9. (a) Horváth, I. T.; Rábai, S. Science 1994, 266, 72.
10. (b) De Wolf, E.; Van Koten, G.; Deelman, G.-J. Chem. Soc. Rev. 1999, 28, 37.
11. Arthel-Rosa, L. P.; Gladysz, J. A. Coord. Chem. Rev. 1999, 190-192, 587.
12. For reviews on catalytic olefin polymerization with transition-metal complexes see: (a) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
13. (b) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. 1995, 34, 1143.
14. (c) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428.
15. (d) Coates, G. W. Chem. Rev. 2000, 100, 1223.
16. (a) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
17. (b) Piers, W. E.; Irvine, G. J.; Williams, V. C. Eur. J. Inorg. Chem. 2000, 2131.
18. (c) Pédeutour, J.-N.; Radhakrishnan, K.; Cramail, G.; Deffieux, A. Macromol. Rapid Commun. 2001, 22, 1095.
19. (a) Chen, Y.-X.; Metz, M. V.; Li, L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 6287.
20. (b) Metz, M. V.; Schwartz, D. J.; Stern, C. L.; Marks, T. J.; Nickias, P. N. Organometallics 2002, 21, 4159.
21. (a) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89.
22. (b) Plenio, H. Chem. Rev. 1997, 97, 3363.
23. (a) Siedle, A. R.; Newmark, R. A.; Lamanna, W. M.; Huffman, J. C. Organometallics 1993, 12, 1491.
24. (b) Burlakov, V. V.; Pellny, P.-M.; Arndt, P.; Baumann, W.; Spannenberg, A.; Shur, V. B.; Rosenthal, U. Chem. Commun. 2000, 241.
25. (a) Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1991, 10, 840.
26. (b) Horton, A. D.; Orpen, A. G. Organometallics 1991, 10, 3910.
27. (c) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
28. Bouwkamp, M. W.; De Wolf, J.; Del Hierro Morales, I.; Gercama, J.; Meetsma, A.; Troyanov, S. I.; Hessen, B.; Teuben, J. H. J. Am. Chem. Soc. 2002, 124, 12956.
29. Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Noltemeyer, M.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
30. Luinstra, G. A.; Ten Cate, L. C.; Heeres, H. J.; Pattiasina, J. W.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3227.
31. Curtis, C. J.; Smart, C.; Robbins, J. L. Organometallics 1985, 4, 1283.
32. Eshuis, J. J. W.; Tan, Y. Y.; Meetsma, A.; Teuben, J. H.; Renkema, J.; Evens, G. G. Organometallics 1992, 11, 362.
33. (a) Evans, W. J.; Seibel, C. A.; Ziller, J. W. J. Am. Chem. Soc. 1998, 720, 6745.
34. (b) Calderazzo, F.; Ferri, I.; Pampaloni, G. Organometallics 1999, 18, 2452.
35. (c) Evans, W. J.; Nyce, G. W.; Forrestal, K. J.; Ziller, J. W. Organometallics 2002, 21, 1050.
36. Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
37. Horton, A. D.; Frijns, J. H. G. Angew. Chem., Int. Ed. 1991, 30, 1152.
38. Kupfer, V.; Thewalt, U.; Tišlerová, I.; Štepnička, P.; Gyepes, R.; Kubišta, J.; Horáček, M.; Mach, K. J. Organomet Chem. 2001, 620, 39.
39. Bottomley, F.; Paez, D. E.; White, P. S. J. Organomet. Chem. 1985, 291, 35.
40. Lukens, W. W., Jr.; Smith, M. R., III; Anderson, R. A. J. Am. Chem. Soc. 1996, 118, 1719.
41. Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132.
42. It should be noted that the C-F bond length observed in the structure of fluorobenzene itself is elongated as well because of C-F⋯H interactions in the solid state. Thalladi, V. L.; Weiss, H.-C.; Blaser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702.
43. (a) Nieman, J.; Teuben, J. H.; Huffman, J. C.; Caulton, K. G. J. Organomet. Chem. 1983, 255, 193.
44. (b) Hessen, B.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1989, 111, 5977.
45. (c) Choukroun, R.; Couziech, B.; Pan, C.; Dahan, F.; Cassoux, P. Organometallics 1995, 14, 4471.
46. Evans, W. J.; Ulibarri, T. A.; Chamberlain, L. R.; Ziller, J. W.; Alvares, D. Organometallics 1990, 9, 2124.
47. Schumann, H.; Winterfeld, J.; Keitsch, M. R.; Herrmann, K.; Demtschuk, J. Z. Anorg. Allg. Chem. 1996, 622, 1457.
48. (a) Merola, J. S.; Campo, K. S.; Gentile, R. A.; Modrick, M. A. Inorg. Chim. Acta 1989, 195, 87.
49. (b) Ohff, A.; Kempe, R.; Baumann, W.; Rosenthal, U. J. Organomet. Chem. 1996, 520, 241.
50. (c) Ahlers, W.; Temme, B.; Erker, G.; Fröhlich, R.; Zippel, F. Organometallics 1997, 16, 1440.
51. (d) Plecnik, C. E.; Liu, F. C.; Liu, S. M.; Liu, J. P.; Meyers, E. A.; Shore, S. G. Organometallics 2001, 20, 3599.
52. (a) Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
53. (b) Green, J. C. Chem. Soc. Rev. 1998, 27, 263.
54. Choukroun, R.; Douziech, B.; Pan, C.; Dahan, F.; Cassoux, P. Organometallics 1995, 14, 4471.
55. (a) Calderazzo, F.; Bacciarelli, S. Inorg. Chem. 1963, 2, 721.
56. (b) Calderazzo, F.; Ferri, I.; Pampaloni, G. Organometallics 1999, 18, 2452.
57. (a) Dawoodi, Z.; Green, M. L. H.; Mtetwa, V. S. B.; Prout, K. Chem. Commun. 1982, 802.
58. (b) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289.
59. (c) Hyla-Krypsin, I.; Gleiter, R.; Kruger, C.; Zwettler, R.; Erker, G. Organometallics 1990, 9, 517.
60. (d) Bochmann, M.; Lancaster, S. J.; Hursthouse, M. B.; Abdul Malik, K. M. Organometallics 1994, 13, 2235.
61. (e) Pindado, G. J.; Thornton-Pett, M.; Bouwkamp, M. W.; Meetsma, A.; Hessen, B.; Bochmann, M. Angew. Chem., Int. Ed. 1997, 36, 2358.
62. (f) Nakamura, H.; Nakayama, Y.; Yasuda, H.; Maruo, T.; Kanehisa, N.; Kai, Y. Organometallics 2000, 19, 5392.
63. (g) Schmitt, O.; Wolmershäuser, G.; Sitzmann, H. Eur. J. Inorg. Chem. 2003. 3105.
64. (a) Kullawiek, R. J.; Faller, J. W.; Crabtree, R. H. Organometallics 1990, 9, 745.
65. (b) Butts, M. D.; Scott, B. L.; Kubas, G. J. J. Am. Chem. Soc. 1996, 118, 11831.
66. (c) Powell, J.; Horvath, M. J.; Lough, A. J. Chem. Soc., Dalton Trans. 1996, 1669.
67. (d) Wu, F.; Dash, A. K.; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 15360.
68. (a) Crabtree, R. H.; Faller, J. W.; Mellea, M. F.; Quirck, J. M. Organometallics 1982, 1, 1361.
69. (b) Powell, J.; Lough, A.; Saeed, T. J. Chem. Soc., Dalton Trans. 1997, 4137.
70. Williard, P. G.; Liu, Q. Y. J. Org. Chem. 1994, 59, 1596.
71. Measured at the Microanalytical Department of H. Kolbe (Mülheim an der Ruhr).
72. Measured at the Microanalytical Department of the University of Groningen.
73. (a) Ahlrichs, R. et al. Turbomole, version 5; Theoretical Chemistry Group, University of Karlsruhe, January 2002.
74. (b) Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346.
75. (c) Turbomole basis set library. Turbomole, version 5; see 38a.
76. (d) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
77. (a) PQS, version 2.4; Parallel Quantum Solutions: Fayetteville, AR, 2001; the Baker optimizer is available separately from PQS upon request.
78. (b) Baker, J. J. Comput. Chem. 1986, 7, 385.
79. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3089.
80. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
81. Eichkorn, K.; Weigend, F.; Treutler, O.; Ahlrichs, R. Theor. Chem. Acc. 1997, 97, 119.