The role of hydrogens in stabilizing organic ions

Canadian Journal of Chemistry

Volumn 74, Issue 6, 1996, Pages 892-900

  Wiberg, Kenneth B ^a   Schleyer, Paul Von Rague ^b   Streitwieser, Andrew ^c  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Anions; Cations; Electron density; Radical cations; polarization

Indexed keywords

ATOMS; CARRIER CONCENTRATION; CHARGE TRANSFER; ELECTROSTATICS; FREE RADICALS; HYDROGEN; MOLECULES; PHOTOELECTRON SPECTROSCOPY; POLARIZATION; PROTONS;

BADER'S THEORY OF ATOMS IN MOLECULES; ELECTRON DENSITY; ELECTRON LOSS; ELECTROSTATIC ENERGY; MOLECULAR ORBITAL THEORY; ORGANIC IONS; RADICAL CATIONS;

IONS;

EID: 0030170168     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-098     Document Type: Article

References (26)

1. E.M. Purcell. Electricity and magnetism. Vol. 2. 2nd ed. McGraw-Hill, New York. 1985.
2. C. Møller and M.S. Plesset. Phys. Rev. 46, 618 (1934).
3. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch, J. Phys. Chem. 98, 11623 (1994); A.D. Becke. J. Chem. Phys. 98, 5648 (1993); C. Lee, W. Yang, and R.G. Parr. Phys. Rev. B: Condens. Matter, 37, 785 (1988).
4. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch, J. Phys. Chem. 98, 11623 (1994); A.D. Becke. J. Chem. Phys. 98, 5648 (1993); C. Lee, W. Yang, and R.G. Parr. Phys. Rev. B: Condens. Matter, 37, 785 (1988).
5. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch, J. Phys. Chem. 98, 11623 (1994); A.D. Becke. J. Chem. Phys. 98, 5648 (1993); C. Lee, W. Yang, and R.G. Parr. Phys. Rev. B: Condens. Matter, 37, 785 (1988).
6. R.F.W. Bader. Atoms in molecules. A quantum theory. Clarendon Press, Oxford. 1990.
7. D.W. Turner, C. Baker, C.R. Baker. Molecular photoelectron spectroscopy. Wiley, New York. 1970.
8. K.B. Wiberg, C.M. Hadad, S. Sieber, and P.v.R. Schleyer. J. Am. Chem. Soc. 114, 5820 (1992).
9. A. Greenberg, R. Winkler, B.L. Smith, and J.F. Liebman. J. Chem. Educ. 58, 367 (1982).
10. R.S. Mulliken and P. Politzer. J. Chem. Phys. 55, 5135 (1971); D.D. Grier and A. Streitwieser. J. Am. Chem. Soc. 104, 3556 (1982).
11. R.S. Mulliken and P. Politzer. J. Chem. Phys. 55, 5135 (1971); D.D. Grier and A. Streitwieser. J. Am. Chem. Soc. 104, 3556 (1982).
12. R.F.W. Bader. Can. J. Chem. 64, 1036 (1986).
13. W. Koch, B. Liu, and P.v.R. Schleyer. J. Am. Chem. Soc. 111, 3479 (1989); P.v.R. Schleyer, W. Koch, B. Liu, and U. Fleisher. J. Chem. Soc. Chem. Commun. 1098 (1989); P.v.R. Schleyer, P. Buzek, and B. Liu. Croat. Chim. Acta, 65, 655 (1992).
14. W. Koch, B. Liu, and P.v.R. Schleyer. J. Am. Chem. Soc. 111, 3479 (1989); P.v.R. Schleyer, W. Koch, B. Liu, and U. Fleisher. J. Chem. Soc. Chem. Commun. 1098 (1989); P.v.R. Schleyer, P. Buzek, and B. Liu. Croat. Chim. Acta, 65, 655 (1992).
15. W. Koch, B. Liu, and P.v.R. Schleyer. J. Am. Chem. Soc. 111, 3479 (1989); P.v.R. Schleyer, W. Koch, B. Liu, and U. Fleisher. J. Chem. Soc. Chem. Commun. 1098 (1989); P.v.R. Schleyer, P. Buzek, and B. Liu. Croat. Chim. Acta, 65, 655 (1992).
16. S. Sieber, P. Buzek, P.v.R. Schleyer, W. Koch, and J.W. de M. Carneiro. J. Am. Chem. Soc. 115, 259 (1993).
17. P.v.R. Schleyer, G.W. Spitznagel, and J. Chandrasekhar. Tetrahedron Lett. 27, 4411 (1986); C.H. DePuy, V.M. Bierbaum, and R. Damrauer. J. Am. Chem. Soc. 106, 4051 (1984).
18. P.v.R. Schleyer, G.W. Spitznagel, and J. Chandrasekhar. Tetrahedron Lett. 27, 4411 (1986); C.H. DePuy, V.M. Bierbaum, and R. Damrauer. J. Am. Chem. Soc. 106, 4051 (1984).
19. K.K. Anderson and S.R. Kass. Tetrahedron Lett. 30, 3045 (1989).
20. H.M. Walborsky and J.M. Motes. J. Am. Chem. Soc. 92, 2445 (1970).
21. P.K. Chou and S.R. Kass. J. Am. Chem. Soc. 110, 7899 (1988).
22. K.B. Wiberg, C.M. Breneman, and T.J. LePage. J. Am. Chem. Soc. 112, 61 (1990).
23. K.B. Wiberg, J. Ochterski, and A. Stretwieser. J. Am. Chem. Soc. Submitted.
24. 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. Ortis, J.B. Foresman, J. Cioslowski, B.B. Sefanov, A. Nanayakkara, M. Challacombe, 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, and J.A. Pople. Gaussian 95, Development Version (Rev. B.I). Gaussian, Inc., Pittsburgh, Pa. 1995.
25. F.W. Biegler-König, R.F.W. Bader, T.-H. Tang. J. Comput. Chem. 3, 317 (1982).
26. P.R. Rablen and C.M. Hadad. Yale University.