Crystal structure of a stable silabenzene and its photochemical valence isomerization into the corresponding silabenzvalene [7]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5648-5649

  Wakita, Keiji ^a,b,e   Tokitoh, Norihiro ^b,e   Okazaki, Renji ^c   Takagi, Nozomi ^d   Nagase, Shigeru ^d  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c JAPAN WOMEN'S UNIVERSITY   (Japan)

^d TOKYO METROPOLITAN UNIVERSITY   (Japan)

^e KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; SILABENZENE; SILABENZVALENE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL BINDING; CRYSTAL STRUCTURE; CRYSTALLIZATION; ISOMERISM; LETTER; MOLECULAR HYBRIDIZATION; MOLECULAR MODEL; MOLECULAR STABILITY; PHOTOCHEMISTRY; PHOTOLYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0034647203     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000309i     Document Type: Letter

References (26)

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2. For reviews of silaaromatic compounds, see: (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419. (b) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 1102-1108. (c) Apeloig Y. ibid., pp 151-166. (d) Brook, A. G.; Brook, M. A. Adv. Organomet. Chem. 1996, 39, 71. (e) Apeloig, Y.; Karni, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; , Vol. 2, Chapter 1.
3. For reviews of silaaromatic compounds, see: (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419. (b) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 1102-1108. (c) Apeloig Y. ibid., pp 151-166. (d) Brook, A. G.; Brook, M. A. Adv. Organomet. Chem. 1996, 39, 71. (e) Apeloig, Y.; Karni, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; , Vol. 2, Chapter 1.
4. For reviews of silaaromatic compounds, see: (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419. (b) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 1102-1108. (c) Apeloig Y. ibid., pp 151-166. (d) Brook, A. G.; Brook, M. A. Adv. Organomet. Chem. 1996, 39, 71. (e) Apeloig, Y.; Karni, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; , Vol. 2, Chapter 1.
5. For reviews of silaaromatic compounds, see: (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419. (b) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 1102-1108. (c) Apeloig Y. ibid., pp 151-166. (d) Brook, A. G.; Brook, M. A. Adv. Organomet. Chem. 1996, 39, 71. (e) Apeloig, Y.; Karni, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; , Vol. 2, Chapter 1.
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10. 2 (all data) = 0.258 for 9446 reflections and 411 parameters.
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12. Sum of the bond angles around the central Si atom and that of the interior bond angles of the silabenzene ring are 359.8(3)° and 720.0(9)°, respectively.
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16. Calculations were carried out using the Gaussian 98 program. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
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21. 4). A 1:4 mixture of 2 and 5 was obtained after irradiation of 15 h. Longer time of irradiation gave polymeric products.
22. Williams, E. A. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; p 536.
23. The structure of 6 was determined by spectroscopic data and X-ray crystallographic analysts. Only this stereoisomer was obtained. See Supporting Information for details.
24. s1 = 93.64) remained after the irradiation (see ref 14).
25. Ando, W.; Shiba, T.; Hidaka, T.; Morihashi, K.; Kikuchi, O. J. Am. Chem. Soc. 1997, 119, 3629. Two Si atoms of the disilabenzvalene resonated at -61.9 ppm. The disilabenzvalene was also air- and moisture-sensitive.
26. Chandrasekhar, J.; Schleyer, P. v. R.; Baumgartner, R. O. W.; Reetz, M. T. J. Org. Chem. 1983, 48, 3453.