The presence and absence of agostic electrostatic Si-H⋯M interactions in [M{Me2Si(H)N-t-Bu}] (M = Li, Mg1/2) species

Organometallics

Volumn 16, Issue 26, 1997, Pages 5999-6003

  Goldfuss, Bernd ^a,b   Schleyer, Paul Von Ragué ^a   Handschuh, Sandra ^a   Hampel, Frank ^a   Bauer, Walter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001735831     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970656+     Document Type: Article

References (63)

1. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
2. (a) Schneider, J. J. Angew. Chem. 1996, 108, 1132; Angew. Chem., Int. Ed. Engl. 1996, 35, 1068.
3. (a) Schneider, J. J. Angew. Chem. 1996, 108, 1132; Angew. Chem., Int. Ed. Engl. 1996, 35, 1068.
4. (b) Schubert, U. Adv. Organomet. Chem. 1990, 30, 151.
5. (c) Bauer, W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1989, 111, 7191.
6. (a) Strout, D. L.; Zaric, S.; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068.
7. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
8. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson T. H. Acc. Chem. Res. 1995, 28, 154.
9. (d) Hofmann, P. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H., Eds.; Springer: Berlin, 1987; p 1.
10. (a) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; Vol. II, P 1458.
11. (b) Fryzuk, M. D.; Rosenberg, L.; Rettig, S. J. Organometallics 1996, 15, 2871.
12. (c) Hermann, P. In Silicon Chemistry; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1993; p 231.
13. (d) Hofmann, P.; Meier, C.; Killer, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51.
14. Tilley, T. D. Acc. Chem. Res. 1993, 26, 22 and references therein.
15. Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1996, 118, 12183.
16. Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. J. Am. Chem. Soc. 1997, 119, 1072.
17. Goldfuss, B.; Schleyer, P. v. R.; Hampel, F. Organometallics, in press.
18. The Allred-Rochow electronegativities of H and Si are 2.2 and 1.74, respectively: (a) Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989.
19. (b) Pawlenko, S. Organosilicon Chemistry; de Gruyter: Berlin, 1986.
20. (a) Streitwieser, A.; Bachrach, S. M.; Dorigo, A.; Schleyer, P. v. R. In Lithium Chemistry; Sapse, A.-M., Schleyer, P. v. R., Eds.; Wiley: New York, 1995.
21. (b) Lambert, C.; Schleyer, P. v. R. Angew. Chem. 1994, 106, 1187; Angew. Chem., Int. Ed. Engl. 1994, 33, 1129.
22. (b) Lambert, C.; Schleyer, P. v. R. Angew. Chem. 1994, 106, 1187; Angew. Chem., Int. Ed. Engl. 1994, 33, 1129.
23. (c) Lambert, C.; Schleyer, P. v. R. In Houben-Weyl Methods of Organic Chemistry, 4th ed.; Thieme: Stuttgart, Germany, 1993; Vol. E19d, p 1.
24. Schleyer, P. v. R.; Clark, T. J. Chem. Soc., Chem. Commun. 1986, 1371.
25. Pritzkow, H.; Lobreyer, T.; Sundermeyer, W.; Hommes, N. J. R. v. E.; Schleyer, P. v. R. Angew. Chem. 1994, 106, 221; Angew. Chem., Int. Ed. Engl. 1994, 33, 126.
26. Pritzkow, H.; Lobreyer, T.; Sundermeyer, W.; Hommes, N. J. R. v. E.; Schleyer, P. v. R. Angew. Chem. 1994, 106, 221; Angew. Chem., Int. Ed. Engl. 1994, 33, 126.
27. Veith, M.; Zimmer, M.; Kosse, P. Chem. Ber. 1994, 127, 2099.
28. Becker, G.; Abele, S.; Dautel, J.; Motz, G.; Schwarz, W. In Organosilicon Chemistry II; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1996.
29. Kosse, P.; Popowski, E.; Veith, M.; Much, V. Chem. Ber. 1994, 127, 2103.
30. (a) Luo, X.-L.; Kubas, G. J.; Bryan, J. C.; Burns, C. J.; Unkefer, C. J. J. Am. Chem. Soc. 1994, 116, 10312.
31. (b) Fan, M.-F.; Jia, G.; Lin, Z. J. Am. Chem. Soc. 1996, 118, 9915.
32. Spaltenstein, E.; Palma, P.; Kreutzer, K. A.; Willoughby, C. A.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 10308.
33. Delpech, F.; Sabo-Etienne, S.; Chaudret, B.; Daran, J.-C. J. Am. Chem. Soc. 1997, 119, 3167.
34. Procopio, L. J.; Carroll, P. J.; Berry, D. H. J. Am. Chem. Soc. 1994, 116, 177.
35. Rees, W. S., Jr.; Just, O.; Schumann, H.; Weinmann, R. Angew. Chem. 1996, 108, 481; Angew. Chem., Int. Ed. Engl. 1996, 35, 419.
36. Rees, W. S., Jr.; Just, O.; Schumann, H.; Weinmann, R. Angew. Chem. 1996, 108, 481; Angew. Chem., Int. Ed. Engl. 1996, 35, 419.
37. Herrmann, W. A.; Eppinger, J.; Spiegier, M.; Runte, O.; Anwander, R. Organometallics 1997, 16, 1813.
38. Sekiguchi, A.; Ichinohe, M.; Takahasi, M.; Kabuto C.; Sakurai, H. Angew. Chem. 1997, 109, 1577; Angew. Chem., Int. Ed. Engl. 1997, 36, 1533.
39. (a) Mootz, D.; Zinnius, A.; Bötcher, B. Angew. Chem. 1969, 81, 398; Angew. Chem., Int. Ed. Engl. 1969, 8 378.
40. (a) Mootz, D.; Zinnius, A.; Bötcher, B. Angew. Chem. 1969, 81, 398; Angew. Chem., Int. Ed. Engl. 1969, 8 378.
41. (b) Rogers, R. D.; Atwood, J. L.; Grüning, R. J. Organomet. Chem. 1978, 157, 229.
42. (a) Bauer, W.; Schleyer, P. v. R. Magn. Reson. Chem. 1988, 26, 827.
43. (b) Bauer, W.; Clark, T.; Schleyer, P. v. R. J. Am. Chem. Soc. 1987, 109, 970.
44. (a) Bauer, W. In Lithium Chemistry; Sapse, A.-M., Schleyer, P. v. R., Eds.; Wiley: New York, 1995.
45. (b) Weiss, E. Angew. Chem. 1993, 105, 1565; Angew. Chem., Int. Ed. Engl. 1993, 32, 1501.
46. (b) Weiss, E. Angew. Chem. 1993, 105, 1565; Angew. Chem., Int. Ed. Engl. 1993, 32, 1501.
47. (c) Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
48. (d) Günther, H.; Moskau, D.; Bast, P.; Schmalz, D. Angew. Chem. 1987, 99, 1242; Angew. Chem., Int. Ed. Engl. 1987, 26, 1212.
49. (d) Günther, H.; Moskau, D.; Bast, P.; Schmalz, D. Angew. Chem. 1987, 99, 1242; Angew. Chem., Int. Ed. Engl. 1987, 26, 1212.
50. 2) is ca. +1.5 au: Goldfuss, B.; Schleyer, P. v. R. Unpublished results.
51. Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
52. (a) Wiseman, G. H.; Wheeler, D. R.; Seyferth, D. Organometallics 1986, 5, 146.
53. (b) Jarvie, S. W.; Lewis, D. J. Chem. Soc. 1963, 4758.
54. 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.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; 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 C.3; Gaussian, Inc., Pittsburgh, PA, 1995.
55. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
56. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
57. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
58. (b) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
59. (a) Wolinski, R. F. W.; Hilton, F. J.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
60. (b) Dodds, J. L.; McWeeney, R.; Sadlej, A. J. Mol. Phys. 1980, 41, 1419.
61. (c) Ditchfield, R. Mol. Phys. 1974, 27, 789.
62. (d) McWeeny, R. Phys. Rev. 1962, 126, 1028.
63. (e) London, F. J. Phys. Radium 1937, 8, 397.