Formation of Hypervalent Complexes of PhCCSiF3 with Pyridine through Intermolecular Silicon⋯Nitrogen Interaction

Journal of the American Chemical Society

Volumn 126, Issue 11, 2004, Pages 3436-3437

  Nakash, Moshe ^a   Goldvaser, Michael ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; SILANE DERIVATIVE; TRIFLUOROPHENYLETHYNYLSILANE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; COOLING; ISOMERISM; MOLECULAR INTERACTION; QUANTUM MECHANICS; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 1642371579     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031801f     Document Type: Article

References (22)

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3. (b) The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley, Chichester, 1989.
4. 19F NMR, and its synthetic details are presented in the Supporting Information.
5. For recent reviews on hypervalent silicon compounds, see: (a) Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; pp 1339-1445.
6. (b) Pestunovich, V.; Kirpichenko S.; Voronkov, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; pp 1447-1537.
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13. 15N one-bond coupling are for pentacoordinated silicon compounds having an intramolecular Si⋯N bond, see: (a) Kalikhman, I.; Krivonos, S.; Kost, D. ; Kottke, T.; Stalke, D. In Organosilicon Chemistry IV: From Molecules to Materials; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, 2000; pp 494-499.
14. (b) Kupce, E.; Liepins, E.; Lapsina, A.; Urtane, I.; Zelcans, G.; Lukevics, E. J. Organomet. Chem. 1985, 279, 343.
15. 29Si chemical shifts for pentacoordinate Si usually exhibit an upfield shift relative to tetracoordinate Si.
16. 2O in solution).10 Therefore, in the case of silane 1 and Py, we were not able to obtain a reasonably accurate binding constant for the formation of the 1·Py complex.
17. See Supporting Information for details.
18. 3 (see Figure 1, left side).
19. (b) Upfield shift upon cooling and downfield shift upon increasing the temperature were found for pentacoordinate silicon structures having an intramolecular Si⋯N bond and were used as a measure for the existence of coordination between the silicon and the coordinating nitrogen, see: Helmer, B. J.; West, R.; Corriu, R. J. P.; Poirier, M.; Royo, G.; De Saxce, A. J. Organomet. Chem. 1983, 251, 295.
20. The only reported coupling across the Si⋯N coordinative bond is related to hexacoordinate silicon compounds having intramolecular Si⋯N bonds, see: Kalikhman, I.; Krivonos, S.; Stalke, D.; Kottke, T.; Kost, D. Organometallics 1997, 16, 3255.
21. Unfortunately, many attempts to obtain crystals suitable for X-ray crystallography for the complexes of 1 with Py from different solvents combinations and temperatures were unsuccessful.
22. Macomber, R. S. J. Chem. Educ. 1992, 69, 375 and references therein.