The U=C double bond: Synthesis and study of uranium nucleophilic carbene complexes

Journal of the American Chemical Society

Volumn 131, Issue 3, 2009, Pages 963-972

  Cantat, Thibault ^b   Arliguie, Thérèse ^a   Noël, Anne ^a   Thuéry, Pierre ^a   Ephritikhine, Michel ^a   Floch, Pascal Le ^b   Mézailles, Nicolas ^b  

^a CNRS UMR 3299   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE COMPLEXES; CARBON BOND; CARBONYL DERIVATIVES; D ORBITALS; DFT CALCULATION; DOUBLE BONDS; MULTIPLE BONDS; X RAY CRYSTAL STRUCTURES;

SULFUR COMPOUNDS; TRANSURANIUM ELEMENTS; URANIUM;

URANIUM COMPOUNDS;

CARBENOID; CARBON; NUCLEOPHILE; URANIUM DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

EID: 67849132297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807282s     Document Type: Article

References (68)

1. Che, C. M.; Ho, C. M.; Huang, J. S. Coord. Chem. Rev. 2007, 251, 2145, and references therein.
2. (a). Arnold, P. L.; Liddle, S. T. Chem. Commun. 2006, 3959.
3. (b). Giesbrecht, G. R.; Gordon, J. C. Dalton Trans. 2004, 2387.
4. (a). Andrews, L.; Cho, H. G. Organometallics 2006, 25, 4040.
5. (b). Lyon, J. T.; Andrews, L.; Hu, H. S.; Li, J. Inorg. Chem. 2008, 47, 1435.
6. (a). Villiers, C.; Ephritikhine, M. ChemsEur. J. 2001, 7, 3043.
7. (b). Villiers, C.; Vandais, A.; Ephritikhine, M. J. Organomet. Chem. 2001, 617-618, 744.
8. (a). Cramer, R. E.; Maynard, R. B.; Paw, J. C.; Gilje, J. W. J. Am. Chem. Soc. 1981, 103, 3589.
9. (b). Cramer, R. E.; Maynard, R. B.; Paw, J. C.; Gilje, J. W. Organometallics 1983, 2, 1336.
10. (c). Stevens, R. C.; Bau, R.; Cramer, R. E.; Afzal, D.; Gilje, J. W.; Koetzle, T. F. Organometallics 1990, 9, 694.
11. Aparna, K.; Ferguson, M.; Cavell, R. G. J. Am. Chem. Soc. 2000, 122, 726.
12. Cantat, T.; Mezailles, N.; Auffrant, A; Le Floch, P. Dalton Trans. 2008, 1957.
13. (a). Cantat, T.; Jaroschik, F.; Nief, F.; Ricard, L.; Mézailles, N.; Le Floch, P. Chem. Commun 2005, 5178.
14. (b). Cantat, T.; Jaroschik, F.; Ricard, L.; Le Floch, P.; Nief, F.; Mézailles, N. Organometallics 2006, 25, 1329.
15. Dietrich, H. M.; Törnroos, K. W.; Anwander, R. J. Am. Chem. Soc. 2006, 128, 9298.
16. Cantat, T.; Ricard, L.; Le Floch, P.; Mézailles, N. Organometallics 2006, 25, 4965.
17. (a). Cavell, R. G.; Babu, R. P. K.; Kasani, A.; McDonald, R. J. Am. Chem. Soc. 1999, 121, 5805.
18. (b). Jones, N. D.; Lin, G.; Gossage, R. A.; MacDonald, R.; Cavell, R. G. Organometallics 2003, 22, 2832.
19. (c). Lin, G.; Jones, N. D.; McDonald, R.; Cavell, R. G. Angew. Chem., Int. Ed. 2003, 42, 4054.
20. Several groups have recently used the same system with groups 2 and 3 metal centers. (a). Orzechowski, L.; Jansen, G.; Harder, S. J. Am. Chem. Soc. 2006, 128, 14676.
21. (b). Liddle, S. T.; McMaster, J.; Green, J. C.; Arnold, P. L. Chem. Commun. 2008, 1747.
22. (a). Cantat, T.; Mezailles, N.; Ricard, L.; Jean, Y.; Le Floch, P. Angew. Chem., Int. Ed. 2004, 43, 6382.
23. (b). Cantat, T.; Demange, M.; Mézailles, N.; Ricard, L.; Jean, Y.; Le Floch, P. Organometallics 2005, 24, 4838.
24. (c). Cantat, T.; Ricard, L.; Mézailles, N.; Le Floch, P. Organometallics 2006, 25, 6030.
25. Gilheany, D. G. Chem. Rev. 1994, 94, 1339.
26. Aparna, K.; Cavell, R. G.; Ferguson, M. J. Am. Chem. Soc. 2000, 122, 726.
27. (a). Arliguie, T.; Lance, M.; Nierlich, M.; Ephritikhine, M. J. Chem. Soc., Dalton Trans. 1997, 2501.
28. (b). Leverd, P. C.; Lance, M.; Vigner, J.; Nierlich, M.; Ephritikhine, M. J. Chem. Soc., Dalton Trans. 1995, 237.
29. (c). Arliguie, T.; Lance, M.; Nierlich, M.; Vigner, J.; Ephritikhine, M. J. Chem. Soc., Chem. Commun. 1994, 847.
30. (d). Baudry, D.; Bulot, E.; Charpin, P.; Ephritikhine, M.; Lance, M.; Nierlich, M.; Vigner, J. J. Organomet. Chem. 1989, 371, 163.
31. Kepert, D. L. Inorganic Stereochemistry in Inorganic Chemistry Concepts, Vol. 6; Springer-Verlag: Berlin, 1982.
32. Gaunt, A. J.; Scott, B. L.; Neu, M. P. Chem. Commun. 2005, 3215.
33. Roger, M.; Arliguie, T.; Thuery, P.; Fourmigue, M.; Ephritikhine, M. Inorg. Chem. 2005, 44, 594.
34. (a). Leverd, P. C.; Lance, M.; Nierlich, M.; Vigner, J.; Ephritikhine, M. J. Chem. Soc., Dalton Trans. 1994, 3563.
35. (b). Leverd, P. C.; Lance, M.; Nierlich, M.; Vigner, J.; Ephritikhine, M. J. Chem. Soc., Dalton Trans. 1993, 2251.
36. Arliguie, T.; Doux, M.; Mézailles, N.; Thuéry, P.; Le Floch, P.; Ephritikhine, M. Inors. Chem. 2006, 45, 9907.
37. Villiers, C.; Thuery, P.; Ephritikhine, M. Acta Crystallosr., Sect. C 2006, 62, m243.
38. (a). Jantunen, K. C.; Burns, C. J.; Castro-Rodriguez, I.; Da Re, R. E.; Golden, J. T.; Morris, D. E.; Scott, B. L.; Taw, F. L.; Kiplinger, J. L. Organometallics 2004, 23, 4682.
39. (b). Barnea, E.; Andrea, T.; Kapon, M.; Berthet, J. C.; Ephritikhine, M.; Eisen, M. S. J. Am. Chem. Soc. 2004, 126, 10860.
40. Perego, G.; Cesari, M.; Farina, F.; Lugli, G. Acta Crystallogr., Sect. B 1976, 32, 3034.
41. Cramer, R. E.; Roth, S.; Edelmann, F.; Bruck, M. A.; Cohn, K. C.; Gilje, J. W. Organometallics 1989, 8, 1192.
42. (a). Parry, J.; Carmona, E.; Coles, S.; Hursthouse, M. J. Am. Chem. Soc. 1995, 117, 2649.
43. (b). Evans, W. J.; Kozimor, S. A.; Nyce, G. W.; Ziller, J. W. J. Am. Chem. Soc. 2003, 125, 13831.
44. Pugh, D.; Wright, J. A.; Freeman, S.; Danopoulos, A. A. Dalton Trans. 2006, 775.
45. Evans, W. J.; Kozimor, S. A.; Ziller, J. W. Polyhedron 2004, 23, 2689.
46. Arnold, P. L.; Blake, A. J.; Wilson, C. Chem. -Eur. J. 2005, 11, 6095.
47. -, potentially acting as a soft anion, does not react with the carbonyl derivatives.
48. Frisch, M. J. et al. Gaussian 03; Gaussian Inc.: Wallingford, CT, 2004.
49. 3 in Figure 5 and ref 10.
50. For recent examples of the use of DFT calculcations to elucidate the electronic structures of actinide complexes or the rationalization of their reactivities, see: (a). Summerscales, O. T.; Cloke, F. G. N.; Hitchcock, P. B.; Green, J. C.; Hazari, N. J. Am. Chem. Soc. 2006, 128, 9602.
51. (b). Lyon, J. T.; Andrews, L.; Malmqvist, P.-A.; Roos, B.; O.; Yang, T.; Bursten, B. E. Inorg. Chem. 2007, 46, 4917.
52. (c). Evans, W. J.; Kozimor, S. A.; Ziller, J. W.; Kaltsoyannis, N. J. Am. Chem. Soc. 2004, 126, 14533.
53. (d). Castro-Rodriguez, I.; Nakai, H.; Gantzel, P.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 15734.
54. (e). Spencer, L. P.; Yang, P.; Scott, B. L.; Batista, E. R.; Boncella, J. M J. Am. Chem. Soc. 2008, 130, 2930.
55. (f). Graves, C. R.; Yang, P.; Kozimor, S. A.; Vaughn, A. E.; Clark, D. L.; Conradson, S. D.; Schelter, E. J.; Scott, B. L.; Thompson, J. D.; Hay, P. J.; Morris, D. E.; Kiplinger, J. L. J. Am. Chem. Soc. 2008, 130, 5272.
56. (g). Li, J.; Bursten, B. E.; Zhou, M.; Andrews, L. A Inorg. Chem. 2001, 40, 5448.
57. (h). Yang, P.; Warnke, I.; Martin, R. L.; Hay, P. J. Organometallics 2008, 27, 1384.
58. The substitution of the phenyl groups on the P atoms by H atoms has previously proven its accuracy in related transition metal and actinide systems: see for exemple refs 10, 13, and (a). Ingram, K. I. M.; Tassell, M. J.; Gaunt, A. J.; Kaltsoyannis, N. Inorg. Chem. 2008, 47, 7824.
59. 2+] fragment is +1.21.
60. The singly occupied HOMO-1 and HOMO being antibonding between the uranium and sulfur atoms, the bond orders for the U=S bonds is formally lower than 2.
61. Li, J.; Bursten, B. E. J. Am.Chem. Soc. 1997, 119, 9021.
62. Volkov, V. V.; Myakishev, K. G. Radiokhimiya 1980, 22, 745.
63. Hooft, R. W. W. COLLECT; Nonius BV: Delft, The Netherlands, 1998.
64. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
65. Sheldrick, G. M. Acta Crystallosr., Sect. A 2008, 64, 112.
66. Farrugia, L. J. J. Appl. Crystallosr. 1997, 30, 565.
67. Gorelsky, S. I. AOMix: Prosram for Molecular Orbital Analysis, version 6.35; University of Ottawa: Ottawa, Canada, 2007.
68. Gorelsky, S. I.; Lever, A. B. P. J. Orsanomet. Chem. 2001, 635, 187.