SiBr2(Idipp): A stable n-heterocyclic carbene adduct of dibromosilylene

Angewandte Chemie - International Edition

Volumn 48, Issue 31, 2009, Pages 5687-5690

  Filippou, Alexander C ^a   Chernov, Oleg ^a   Schnakenburg, Gregor ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Carbene ligands; Density functional calculations; Donor acceptor systems; Silicon; Silylenes

Indexed keywords

CARBENE LIGANDS; CARBENES; DENSITY FUNCTIONAL CALCULATIONS; DONOR-ACCEPTOR SYSTEMS; IMIDAZOL; N-HETEROCYCLIC CARBENES; NMR SPECTROSCOPY; SILYLENES;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILANES; X RAY CRYSTALLOGRAPHY;

LIGANDS;

EID: 70349918264     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902431     Document Type: Article

References (78)

1. a) M. Schmeißer, P. Voss, Top. Curr. Chem. 1967, 9, 165;
2. b) J. C. Thompson, I. L. Margrave, Science 1967, 155, 669;
3. c) W. H. Atwell, D. R. Weyenberg, Angew. Chem. 1969, 81, 485;
4. Angew. Chem. Int. Ed. Engl. 1969, 8, 469;
5. d) J. L. Margrave, P. W. Wilson, Acc. Chem. Res. 1970, 3, 306;
6. e) P. L. Timms, Adv. Inorg. Radiochem. 1972, 14, 121;
7. f) I L. Margrave, K. G. Sharp, P. W. Wilson, Top. Curr. Chem. 1972, 26, 1;
8. g) C. S. Liu, T.-L. Hwang, Adv. Inorg. Chem. Radiochem. 1985, 29, 1.
9. a) I M. Charig, B. A. Joyce, J. Electrochem. Soc. 1962, 109, 957;
10. b) E. G. Bylander, J. Electrochem. Soc. 1962, 109, 1171;
11. c) E. Sirtl, K. Reuschel, Z. Anorg. Allg. Chem. 1964, 332, 113;
12. d) O. Alstrup, C. O. Thomas, J. Electrochem. Soc. 1965, 112, 319.
13. a) C. P. Kempter, C. Alvarez-Tostado, Z. Anorg. Allg. Chem. 1957, 290, 238;
14. b) H. Schäfer, B. Morcher, Z Anorg. Allg. Chem. 1957, 290, 279.
15. a) H. Schäfer, I. Nickl, Z Anorg. Allg. Chem. 1953, 274, 250;
16. b) A. S. Kana'an, J. L. Margrave, Inorg. Chem. 1964, 3, 1037;
17. c) E. Wolf, C. Herbst, Z Anorg. Allg. Chem. 1966, 347, 112;
18. d) R. Teichmann, E. Wolf, Z Anorg. Allg. Chem. 1966, 347, 145;
19. e) H. Schafer, H. Bruderreck, B. Morcher, Z Anorg. Allg. Chem. 1967, 352, 122.
20. n, see: a) M. Schmeißer, K.-P. Ehlers, Angew. Chem. 1964, 76, 781;
21. b) P. L. Timms, R. A. Kent, T. C. Ehlert, J. L. Margrave, J. Am. Chem. Soc. 1965, 87, 2824.
22. n, see: c) M. Schmeißer, P. Voss, Z Anorg. Allg. Chem. 1964, 334, 50;
23. d) P. W Schenk, H. Bloching, Z Anorg. Allg. Chem. 1964, 334, 57;
24. e) E. Hengge, D. Kovar, Z Anorg. Allg. Chem. 1979, 458, 163;
25. f) H. Stüger, R. Janoschek, Phosphorus Sulfur Silicon Relat. Elem. 1992, 68, 129;
26. g) J. R. Koe, D. R. Powell, J. J. Buffy, S. Hayase, R. West, Angew. Chem. 1998, 110, 1514;
27. Angew. Chem. Int. Ed. 1998, 37, 1441.
28. n, see: h) M. Schmeißer, M. Schwarzmann, Z Naturforsch. B 1956, 11, 278;
29. i) D. Kovar, K. Utvary, E. Hengge, Monatsh. Chem. 1979, 110, 1295;
30. j) H. Stüger, E. Hengge, Monatsh. Chem. 1988, 119, 873.
31. n see: k) M. SchmeiBer, K. Friederich, Angew. Chem. 1964, 76, 782;
32. l) E. Hengge, D. Kovar, Angew. Chem. 1981, 93, 698;
33. Angew. Chem. Int. Ed. Engl. 1981, 20, 678-678;
34. m) C. Kratky, H. Hengge, H. Stüger, A. L. Rheingold, Acta Crystallogr. Sect. C 1985, 41, 824.
35. Molecular silicon(II) compounds are very rare. For a recent publication including all known examples, see: P. Jutzi, K. Leszczynska, B. Neumann, W W Schoeller, H.-G. Stammler, Angew. Chem. 2009, 121, 2634;
36. Angew. Chem. Int. Ed. 2009, 48, 2596.
37. S. P. Kolesnikov, V. I. Shiryaev, O. M. Nefedov, Iz, v. Akad. Nauk SSSR Ser. Khim. 1966, 584.
38. a) W P. Neumann, Chem. Rev. 1991, 91, 311;
39. b) J. Barrau, G. Rima, Coord. Chem. Rev. 1998, 178-180, 593;
40. c) S. E. Boganov, V. I. Faustov, M. P. Egorov, O. M. Nefedov, Russ. Chem. Bull. 2004, 53, 960;
41. d) N. N. Zemlyanskii, I. V. Borisova, M.S. Nechaev, V. N. Khrustalev, V. V. Lunin, M. Y. Antipin, Y. A. Ustynyuk, Russ. Chem. Bull. 2004, 53, 980.
42. Y. Wang, Y. Xie, P. Wei, R. B. Bruce, H. F. Schaefer III, P. von R. Schleyer, G. H. Robinson, Science 2008, 321, 1069.
43. a) A. J. Arduengo III, H. V. R. Dias, C. Calabrese, F. Davidson, Inorg. Chem. 1993, 32, 1541;
44. b) B. Gehrhus, P. B. Hitchcock, M. F. Lappert, J. Chem. Soc. Dalton Trans. 2000, 3094;
45. c) P. A. Rupar, V. N. Stavorevov, P. J. Ragogna, K. M. Baines, J. Am. Chem. Soc. 2007, 129, 15138;
46. d) P. A. Rupar, M. C. Jennings, K. M. Baines, Organometallics 2008, 27, 5043.
47. 2, and Idipp.
48. 3).
49. 2 solution of 1 from ambient temperature to -60 °C. The crystals deteriorate rapidly owing to the loss of the included solvent molecules and should be handled at very low temperature. Suitable yellow crystals of 2 were grown by diffusion of hexane into a benzene solution of 2 at room temperature. CCDC 729736 and CCDC 729737 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
50. a) A. Bondi, J. Phys. Chem. 1964, 68, 441;
51. b) A. M. James, M. P. Lord, in Macmillan's Chemical and Physical Data, Macmillan, London, 1992.
52. i is the individual value and n = 3.
53. T. Iijima, H. Jimbo, M. Taguchi, J. Mol. Struct. 1986, 144, 191.
54. 2) single bond lengths was calculated from a CSD survey of tetravalent, four-coordinate silicon compounds.
55. 4(Idipp) molecules in less polar solvents, such as benzene.
56. G. Engelhardt, R. Radeglia, H. Jancke, E. Lippmaa, M. Magi, Org. Magn. Res. 1973, 5, 561.
57. a) E. A. Williams, I. D. Carglioli, Annu. Rep. NMR Spectrosc. 1979, 9, 221;
58. b) E. A. Williams, Annu. Rep. NMR Spectrosc. 1983, 15, 235.
59. 2 and the carbene planes, respectively. The carbene plane is defined as the least-squares plane of the imidazol-2-ylidene ring.
60. W M. Boesveld, B. Gehrhus, P. B. Hitchcock, M. F. Lappert, P. von R. Schleyer, Chem. Commun. 1999, 755.
61. N. Wiberg, G. Wagner, I. Riede, G. Müller, Organometallics 1987, 6, 32.
62. A. G. Brook, S. C. Nyburg, F. Abdesahen, B. Gutekunst, G. Gutekunst, R. Krishna, M. R. Kallury, Y. C. Poon, Y.-M. Chang, W. Wong-Ng, J. Am. Chem. Soc. 1982, 104, 5667.
63. g is the thermal average distance, which was obtained from electron diffraction: I. Hargittai, G. Schultz, J. Tremmel, N. D. Kagramanov, A. K. Maltsev, O. M. Nefedov, J. Am. Chem. Soc. 1983, 105, 2895;
64. e is the equilibrium distance corresponding to the minimum of the potential energy surface, and was obtained from a joint electron diffraction and vibrational spectroscopic analysis: A. G. Gershikov, N. Y. Subbotina, M. Hargittai, J. Mol. Spectrosc. 1990, 143, 293.
65. A. J. Arduengo III, R. Krafczyk, R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall, M. Unverzagt, Tetrahedron 1999, 55, 14523.
66. NBO 5.0 Program. E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison, 2001.
67. a) E. D. Glendening, F. Weinhold, J. Comput. Chem. 1998, 19, 593;
68. b) E. D. Glendening, F. Weinhold, J. Comput. Chem. 1998, 19, 610.
69. a) W A. Burns, K. R. Leopold, J. Am. Chem. Soc. 1993, 115, 11622;
70. b) V. Jonas, G. Frenking, M. T. Reetz, J. Am. Chem. Soc. 1994, 116, 8741.
71. Resonance structures were found for 2, of which 41 have a resonance weight higher than 1 %. The leading resonance structure has a weight of 4.41 %. 1341
72. 2): H. Ottosson, A. M. Eklöf, Coord. Chem. Rev. 2009, 252, 1287.
73. 2 and Idipp at 0 K plus the correction for the zero-point vibrational energies.
74. a) P. Jutzi, D. Kanne, C. Krüger, Angew. Chem. 1986, 98, 163;
75. Angew. Chem. Int. Ed. Engl. 1986, 25, 164;
76. b) P. Jutzi, U. Holtmann, D. Kanne, C. Krüger, R. Blom, R. Gleiter, I. Hyla-Kryspin, Chem. Ber. 1989, 122, 1629.
77. A. C. Filippou, P. Portius, G. Kociok-Kohn, V. Albrecht, J. Chem. Soc. Dalton Trans. 2000, 1759, and references therein.
78. A. C. Filippou, P. Portius, G. Kociok-Kohn, Chem. Commun. 1998, 2327, and references therein.