Carbon-silicon hyperconjugation and strain-enhanced hyperconjugation: Structures of N-methyl 2- And 4-tert-butyldimethylsilylmethyl pyridinium cations

Organometallics

Volumn 26, Issue 6, 2007, Pages 1361-1364

  Hassall, Kathryn ^a   Lobachevsky, Sofia ^a   Schiesser, Carl H ^a   White, Jonathan M ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; DERIVATIVES; INTERCALATION COMPOUNDS; NITROGEN COMPOUNDS; STRAIN RATE; SUBSTITUTION REACTIONS;

HYPERCONJUGATION; PYRIDINIUM CATIONS; TRIISOPROPYLSILYL DERIVATIVES;

POSITIVE IONS;

EID: 33947680193     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060939e     Document Type: Article

References (17)

1. Lambert, J. B. Tetrahedron 1990, 46, 2677.
2. White, J. M.; Clark, C. I. Topics in Stereochemistry, Denmark, S. E., Ed.; John Wiley and Sons: New York, 1999; Vol. 22, Chapter 3.
3. Wierschke, S. G.; Chandrasekhai, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496.
4. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
5. Lambert, J. B.; Shawl, C. E.; Basso, E. Can. J. Chem. 2000, 78, 1441.
6. Happer, A.; Ng, J.; Pool, B.; White, J. M. J. Organomet. Chem. 2002, 659, 10.
7. Hassall, K.; Lobachevsky, S.; White, J. M. J. Org. Chem. 2005, 70, 1993.
8. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley and Sons: New York, 1976.
9. 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.; Iyenger, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, 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.; Ochterski, 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.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, 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. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
10. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, 4.0; University of Wisconsin: Madison, WI, 1996.
11. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
12. Clinton, N. A.; Brown, R. S.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 5228.
13. White, J. M.; Fifer, N. Org. Biomol. Chem. 2005, 1776.
14. Lew, S. Q.; McClelland, R. A. J. Am. Chem. Soc. 1993, 115, 11516.
15. SMART, SAINT, SADABS; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1999.
16. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
17. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.