NBO analysis of halogen bridging in 4-halo-1-buten-3-yl cations

Journal of Molecular Structure: THEOCHEM

Volumn 822, Issue 1-3, 2007, Pages 8-11

  Haubenstock, H ^a   Sauers, R R ^b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

Allyl cations; Halogen bridging; Hyperconjugation; NBO analysis

Indexed keywords

EID: 34848879866     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.07.005     Document Type: Article

References (15)

1. Haubenstock H., and Sauers R.R. Tetrahedron 60 (2004) 1191
2. White J.C., Cave R.J., and Davidson E.R. J. Am. Chem. Soc. 110 (1988) 6308 These authors define hyperconjugation as "energy lowering that results from the through-space delocalization of electrons". Technically, bridging is a form of hyperconjugation
3. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899
4. F. Weinhold, in: Encyclopedia of Computational Chemistry 3 (1998) 1792.
5. Calculations in this work did not utilize diffuse functions in view of known anomalies; cf. Goodman L., and Sauers R.R. J. Comp. Chem. 28 (2007) 269
6. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh, PA, 1998.
7. NBO version 3.1 is incorporated within this version of the Gaussian suite: D.E. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO, Version 3.1; NBO 5.0. E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, J.A. Bohmann, C.M. Morales, F. Weinhold (Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2001) cf. .
8. Becke A.D. J. Chem. Phys. 98 (1993) 5648
9. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
10. Scott A.P., and Radom L. J. Phys. Chem. 100 (1996) 16502
11. D.R. Lide (Ed.), CRC Handbook of Chemistry and Physics, CRC Press, Inc., Boca Raton, FL, 1990-1991, pp. 10-193-10-209.
12. E.D. Glendening, J.K. Badenhoop, F. Weinhold, University of Wisconsin Theoretical Chemistry Institute Report WI-TCI-803, 1994; see also reference [3b].
13. Studies of regioselectivity in addition reactions of electrophilic halogen reagents to butadiene in a variety of solvents have concluded that the results are consistent with weakly bridged bromonium or chloronium ion intermediates. Heasley V.L., Heasley G.E., Loghry R.A., and McConnell M.R. J. Org. Chem. 37 1 (1972) 2228
14. See also. Shellhamer D.F., Gleason D.C., Vaughan G.G., Ryan A.J., Titterington P.K., Heasley V.L., and Lehman J.J. J. Fluorine Chem. 123 (2003) 171
15. For a related comprehensive study of the effects of bridging on halonium ion structure, see. Shellhamer D.F., Gleason D.C., Rodriguez S.J., Heasley V.L., Boatz J.A., and Lehman J.J. Tetrahedron 62 (2006) 11608