In search of 1,3-disila/germa/stannabicyclo[1.1.1]pentanes with shortbridgehead-bridgehead distances and low ring strain energies

Silicon Chemistry

Volumn 3, Issue 3-4, 2007, Pages 165-173

  Tibbelin, Julius ^a   Sandström, Niclas ^a   Ottosson, Henrik ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Ab initio; Cage compounds; DFT; Group 14 elements; Strain

Indexed keywords

EID: 33845922635     PISSN: 15690660     EISSN: 15728994     Source Type: Journal    
DOI: 10.1007/s11201-006-9016-5     Document Type: Article

References (34)

1. For reviews on strained hydrocarbons see e.g. (a) Wiberg, K.B. 1986 Angew. Chem. Int. Ed. Engl. 25, 2980. (b) Wiberg, K.B. 1996 Acc. Chem. Res. 29, 229.
2. Wiberg, K.B. & Connor, D.S. 1966 J. Am. Chem Soc. 88, 4437.
3. Sandströ, N. & Ottosson, H. 2005 Chem. Eur.J. 11, 5067.
4. Levin, M.D., Kaszynski, P. & Michl, J. 2000 Chem. Rev. 100, 169.
5. McKinley, A.J., Ibrahim, P.N., Balaji, V. & Michl, J. 1992 J. Am. Chem. Soc. 114, 10631.
6. Garcia-Fernandez, H. 1961 Bull. Soc. Chim. Fr. 2453.
7. Choi, N., Asano, K. & Ando W. 1995 Organometallics 14, 3146.
8. Schumann, H. & Benda, H. 1969 Angew. Chem. 24, 1049.
9. Driess, M., Gleiter, R., Janoschek, R., Pritzkow, H. & Reisgys, M. 1994 Angew. Chem. Int. Ed. 33, 1484.
10. Kabe, Y., Kawase, T., Okada, J., Yamashita, O., Goto, M. & Masamune, S. 1990 Angew. Chem. Int. Ed. Engl. 29, 794.
11. Sita, L.R. & Bickerstaff, R.D. 1990 J. Am. Chem. Soc. 112, 8839.
12. Sita, L.R. & Bickerstaff, R.D. 1991 J. Am. Chem. Soc. 113, 5070.
13. Sn-C = 2.14, Sn-N = 2.04, Sn-O = 1.94, Sn-Sn = 2.81, Sn-S = 2.43, Sn-P = 2.54 Å as reported in (a) Mackay, K.M. 1995 The Chemistry of Organic Germanium, Å as reported in (a) Mackay, K.M. The Chemistry of Organic Germanium, Tin and, Lead Compounds, S. Patai (ed), Wiley, Chichester, UK, 1995 Chap. 2, p. 101. and (b) Kennard, O. 1990 CRC Handbook of Chemistry and Physics, 71 st, D. R. Lide (ed.), CRC Press, Boca Raton, Section. 9-1.
14. Wiberg, N., Vasiht, S.K., Fischer G. & Mayer, P., 2004, Z. Anorg. Allg. Chem. 630, 1823.
15. Iwamoto, T., Yin, D., Kabuto, C. & Kira, M. 2001 J. Am. Chem. Soc. 123, 12730.
16. Nagase, S. & Kudo, T. 1988 Organometallics 7, 2534.
17. Nagase, S., Kudo, T. & Kurakake, T.J. 1998 Chem. Soc. Chem. Commun. 1063.
18. Nguyen, K.A., Carroll, M.T. & Gordon, M.S. 1991 J. Am. Chem. Soc. 113, 7924.
19. Gordon, M.S. Nguyen, K.A. & Carroll, M.T. 1991 Polyhedron 10, 1247.
20. Kitchen, D.B., Jackson, J.E., Leland, C. & Allen, C.A. 1990 J. Am. Chem. Soc. 112, 3408.
21. George, P., Trachtman, M., Bock, C.W. & Brett, A.M. 1976 Tetrahedron 32, 317.
22. Liebman, J.F. & Skancke, P.N. 1996 Int. J. Quantum Chem. 58, 707.
23. Gaussian 03, Revision B.05. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E. Robb, M.A., Cheeseman, J.R., Montgomery, J.A. Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cosso, M., Sclmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochteski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Frakas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Oritz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P.P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham. M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M., Johnson, W., B. Chen, W., Wong, M.W, Gonzalez, C. & Pople, J.A. Gaussian, Inc., Pittsburgh, PA, 2001.
24. Becke, A.D. 1993 J. Chem. Phys. 98, 1372.
25. Hay P.J. & Wadt, W.R. 1985 J. Chem. Phys. 82, 270; Hay P.J. & Wadt, W.R. 1985 J. Chem. Phys. 82, 284; Hay P.J. & Wadt, W.R. 1985 J. Chem. Phys. 82, 299.
26. Check, C.E., Faust, T.O., Bailey, J.M., Wright, B.J., Gilbert T.M. & Sunderlin, L.S. 2001 J. Phys. Chem. A 105, 8111.
27. Carpenter, J.E. & Weinhold, F.J. 1988 Mol. Struct. (Theochem) 169, 41.
28. Si-C 1.87 Å, Si-N 1.74 Å, Si-O 1.63 Å, Si-Si 2.34 Å, Si-P 2.264 Å, and Si-S 2.14 Å, as reported in (a) Kaftory, M., Kapon, M. & Botoshansky, M. 1998 The Structural Chemistry of Organosilicon Compounds, In The Chemistry of Organic Silicon Compounds, Vol. 2, Chap. 5., p. 181. Wiley, Chichester, UK, Rappoport, Z.; Apeloig, Y. (Eds.), and (b) Allen, F.H., Kennard, O., Watson, D.G., Brummer, L., Orpen, A.G. & Taylor, R. 1987 J. Chem. Soc., Perkin Trans. II. 1.
29. For 1,3-disilabicyclo[1.1.1]pentanes 1Si-4Si and 8Si-11Si with the X bridge composed of first-row elements, the correlation between strain energy and Si-X-Si angle deformation is r 2 = 0.9066 at MP2/LANL2DZp level and r 2 = 0.9535 at B3LYP/LANL2DZp level.
30. Grigoras, S. & Lane, T.H. 1990 In Silicon-Based Polymer Science, Ziegler, Chap. 7, p. 224, Washington, DC, American Chemical Society, (ACS Adv. Chem. Ser. 224), J. M. & Fearon, F.W. G. (Eds).
31. 3.54 (C).
32. Bondi, A. 1964 J. Phys. Chem. 68, 441.
33. Ge-C = 1.945, Ge-N = 1.85, Ge-O = 1.76, Ge-Ge = 2.45, Ge-S = 2.23, Ge-P = 2.36 Å as reported in (a) Mackay, K.M. The Chemistry of Organic Germanium, Tin and, Lead Compounds, S. Patai (ed), Wiley, Chichester, UK, 1995 Chap. 2, p. 101. and (b) Kennard, O. 1990 CRC Handbook of Chemistry and Physics, 71 st, D.R. Lide (ed.), CRC Press, Boca Raton, Section. 9-1.
34. Garcia, F., Hopkins, A.D., Humphrey, S. M., McPartlin, M., Pask, C. M., Woods, A. D. & Wright, D.S. 2004 Organometallics 23, 4821.