Bis-alkene complexes of stannylium and germylium ions

Organometallics

Volumn 27, Issue 19, 2008, Pages 4847-4853

  Yang, Yu ^b   Panisch, Robin ^a   Bolte, Michael ^b   Müller, Thomas ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC PHYSICS; ATOMS; CHEMICAL REACTIONS; ELECTROLYSIS; FLOW INTERACTIONS; GERMANIUM; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; POSITIVE IONS; SILICON; TIN; TIN COMPOUNDS; TITANIUM COMPOUNDS; VAN DER WAALS FORCES;

APICAL POSITIONS; CARBON ATOMS; CENTRAL ATOMS; COORDINATION GEOMETRIES; DOUBLE BONDS; ELECTRON DENSITIES; FRAGMENTATION REACTIONS; GEOMETRICAL ARRANGEMENTS; GROUP 14 ELEMENTS; INTERACTION ENERGIES; NMR SPECTROSCOPIES; PENTACOORDINATED; PERFLUORINATED; QUANTUM MECHANICAL COMPUTATIONS; VAN DER WAALS; X-RAY STRUCTURE ANALYSIS;

COORDINATION REACTIONS;

EID: 54249157812     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800432x     Document Type: Article

References (52)

1. For recent review, see:(a) Müller, T. Adv. Organomet. Chem. 2005, 53, 155.
2. (b) Zharov, I.; Michl, J. In The Chemistry of Organic Germanium, Tin and Lead Compounds, Vol 2; Rappoport, Z., Ed.; Wiley: Chichester, 2002; p 633.
3. (a) Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds, Vol 2; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; p 1339.
4. (b) Baukov, Y. I.; Tandura, S. N. The Chemistry of Organic Germanium, Tin and Lead Compounds, Vol 2; Rappoport, Z., Ed.; Wiley: Chichester, 2002; p 963.
5. (a) Müller, T.; Bauch, C.; Ostermeier, M.; Boite, M.; Auner, N. J. Am. Chem. Soc. 2003, 125, 2158.
6. (b) Steinberger, H.-U.; Müller, T.; Auner, N.; Maerker, C.; Schleyer, P. v. R. Angew. Chem. 1997, 36, 626.
7. (a) Meyer, R.; Werner, K.; Müller, T. Chem.-Eur. J. 2002, 8, 1163.
8. (b) Choi, N.; Lickiss, P. D.; McPartlin, M.; Masangane, P. D.; Veneziani, G. L. Chem. Commun. 2005, 6023.
9. (c) Panisch, R.; Boite, M.; Müller, T. Organometallics 2007, 26, 3524.
10. Duttwyler, S.; Do, Q.-Q.; Linden, A.; Baldridge, K. K.; Siegel, J. S. Angew. Chem. 2008, 47, 1719.
11. See for example: Elschenbroich, C. Organometallchemie, 6th ed.; Teubner Wiesbaden, 2008.
12. Müller, T.; Bauch, C.; Boite, M.; Auner, N. Chem.-Eur. J. 2003, 9, 1746.
13. Jerkunica, J. M.; Traylor, T. G. J. Am. Chem. Soc. 1971, 93, 6278.
14. (a) Battlett, P. D.; Condon, F. E.; Schneider, A. J. Am. Chem. Soc. 1944, 66, 1531.
15. (b) Deno, N. C.; Peterson, H. J.; Gaines, G. S. Chem. Rev. 1960, 60, 7.
16. (c) Corey, J. Y. J. Am. Chem. Soc. 1975, 97, 3237.
17. (d) Mayr, H.; Basso, N.; Hagen, G. J. Am. Chem. Soc. 1992, 114, 3060.
18. (e) Apeloig, Y.; Merin-Aharoni, O.; Danovich, D.; Ioffe, A.; Shaik, S. Isr. J. Chem. 1993, 33, 387.
19. (f) Lambert, J. B.; Kuhlmann, B. J. Chem. Soc., Chem. Commun. 1992, 931.
20. (a) Lambert, J. B.; Zhao, Y.; Wu, H.; Tse, W. C.; Kuhlmann, B. J. Am. Chem. Soc. 1999, 121, 5001.
21. (b) Lambert, J. B.; Zhao, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 400.
22. (c) Lambert, J. B.; Lin, L. J. Org. Chem. 2001, 66, 8537.
23. (d) Lambert, J. B.; Lin, L.; Keinan, S.; Müller, T. J. Am. Chem. Soc. 2003, 125, 6022.
24. (e) Kim, K.-C.; Reed, C. A.; Elliot, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 297, 825.
25. +, is accompanied by a significant low-field shift of the Sn resonance. For the basic theory, see: Ramsey, N. F. Phys. Rev. 1950, 78, 699.
26. (a) Blackwell, J. M.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 1295.
27. (b) Henderson, L. D.; Piers, W. D.; Irvine, G. J.; McDonald, R. Organometallics 2002, 21, 340.
28. (a) Wrackmeyer, B. Annu. Rep. NMR Spectrosc. 1985, 16, 73.
29. (b) Wrackmeyer, B.; Kundler, S.; Boese, R. Chem. Ber. 1993, 126, 1361.
30. All computations were done using: Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian Inc.: Pittsburgh, PA, 2003.
31. Bondi, A. J. Phys. Chem. 1964, 68, 441.
32. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1; Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 1996.
33. For a monograph on the methodology, see: Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, 1990.
34. The topological analysis of the charge density was done with the AIM 2000 program: (a) Biegler-König, F.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545. For a monograph on the methodology, see:
35. (b) Biegler-König, F.; Schonbohm, J. J. Comput. Chem. 2002, 23, 1489.
36. Chemical bonds between a pair of atoms can be identified by (3,-1) critical points (the so-called bond critical points, bcp) of the charge density. At such bcp's the gradient vector of p(r) vanishes and the Hessian matrix of ρ(r) at bcp has three nonvanishing eigenvalues, two of which are negative. The positive eigenvalue is associated with the bond path itself along which the charge density ρ(r) reaches a minimum at the bcp.
37. -5; ε = 0.
38. b,)- B)}. Using HF/6-311G(d,p)//MP2/6-311G(d,p) wave functions for ethane, ethene, benzene, and ethyne, a least-squares fit to bond orders of 1, 2, 1.5, and 3 yields A = 7.56716 and B = 1.90631 for C-C bonds.
39. (a) Werstiuk, N. H.; Muchall, H. M. THEOCHEM 1999, 463, 225.
40. (b) Werstiuk, N. H.; Muchall, H. M. J. Phys, Chem. A 2000, 104, 2054.
41. (a) Cremer, D.; Kraka, E. J. Am. Chem. Soc. 1985, 107, 3800.
42. (b) Olsson, L.; Cremer, D. Chem. Phys. Lett. 1993, 215, 433.
43. (a) Becke, A. D. Phys. Rev. 1988, A 38, 3098.
44. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
45. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
46. (d) Johnson, B. G.; Gill, P. M. W.; Pople, J. A. (25) SDD Stuttgart Dresden pseudopotentials: Quasirelativistic effective core potentials (ECPs) for Si, Ge, Sn: Bergner, A.; Dolg, M.; Stell, H.; Preuss, H. Mol. Phys. 1993, 80, 1431.
47. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
48. (b) Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503.
49. (a) Hosomi, A.; Mikami, M.; Sakurai, H. Bull. Chem. Soc. Jpn. 1983, 56, 2784.
50. Bauch, C. Ph.D. Thesis, Goethe University Frankfurt, 2003.
51. (a) Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 245.
52. (b) Chien, J. C. W.; Tsai, W.-M.; Rausch, M. D. J. Am. Chem. Soc. 1991, 113, 8570.