The 2-norbornyl cation is a π-complex, not a σ-bridged, nonclassical species: An AIM study

Journal of Molecular Structure: THEOCHEM

Volumn 463, Issue 3, 1999, Pages 225-229

  Werstiuk, Nick H ^a   Muchall, Heidi M ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

complex; 2 Norbornyl cation; Atoms in molecules (AIM); Becke3LYP

Indexed keywords

BICYCLO COMPOUND; CATION; NORBORNANE DERIVATIVE;

ARTICLE; ATOM; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS;

EID: 0033519159     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(98)00625-3     Document Type: Article

References (29)

1. H.M. Muchall, N.H. Werstiuk, Can. J. Chem., in press.
2. Winstein S., Trifan D.S. J. Am. Chem. Soc. 71:1949;2953.
3. Winstein S., Trifan D. J. Am. Chem. Soc. 74:1952;1147.
4. Winstein S., Trifan D. J. Am. Chem. Soc. 74:1952;1154.
5. Roberts J.D., Lee C.C., Saunders W.H. J. Am. Chem. Soc. 76:1954;4501.
6. Olah G.A., White A.M. J. Am. Chem. Soc. 94:1972;808.
7. Dewar M.J.S., Marchand A.P. Ann. Rev. Phys. Chem. 16:1965;321.
8. Jensen F.R., Smart B.E. J. Am. Chem. Soc. 91:1969;5686.
9. Jensen F.R., Smart B.E. J. Am. Chem. Soc. 91:1969;5688.
10. Traylor T.G., Hanstein W., Berwin H.J., Clinton N.A., Brown R.S. J. Am. Chem. Soc. 93:1971;5715.
11. Brown H.C. The Nonclassical Ion Problem. 1977;Plenum Press, New York.
12. Bader R.F.W. Atoms in Molecules. A Quantum Theory. 1990;Clarendon Press, Oxford.
13. Perera S.A., Bartlett R.J. J. Am. Chem. Soc. 118:1996;7849.
14. Schreiner P.R., Severance D.L., Jorgensen W.L., Schleyer P.v.R., Schaefer H.F. III. J. Am. Chem. Soc. 117:1995;2663.
15. A.D. Becke, J. Chem. Phys., 98 (1993) 5648; C. Lee, W. Yang, R.G. Parr. Phys. Rev. B, 37 (1988) 785.
16. A.D. Becke, J. Chem. Phys., 98 (1993) 5648; C. Lee, W. Yang, R.G. Parr. Phys. Rev. B, 37 (1988) 785.
17. Bader R.F.W. Acc. Chem. Res. 18:1985;9.
18. Schleyer P.v.R., Sieber S. Angew. Chem. Int. Ed. Engl. 32:1993;1606.
19. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople. Gaussian 94, Revision B.3. Gaussian, Inc., Pittsburgh, PA. 1995.
20. Biegler-König F.W., Bader R.F.W., Tang T.-H. J. Comp. Chem. 3:1982;317.
21. Hertwig R.H., Koch W., Schröder D., Schwarz H., Hrušák J., Schwerdtfeger P. J. Phys. Chem. 100:1996;12253.
22. Laube T. Helv. Chim. Acta. 77:1994;943.
23. Laube T. Acc. Chem. Res. 28:1995;399.
24. H.M. Muchall, N.H. Werstiuk, J. Am. Chem. Soc., submitted.
25. Walborsky H.M., Baum M.E., Youssef A.A. J. Am. Chem. Soc. 83:1961;988.
26. Goering H.L., Sloan M.F. J. Am. Chem. Soc. 83:1961;1397.
27. Winstein S., Carter P. J. Am. Chem. Soc. 83:1961;4485.
28. Hogeveen H., Kwant P.W. J. Am. Chem. Soc. 96:1974;2208.
29. Cremer D., Kraka E., Slee T.S., Bader R.F.W., Lau C.D.H., Nguyen-Dang T.T., MacDougall P.J. J. Am. Chem. Soc. 105:1983;5069.