CH3+ is the most trivial carbocation, but are its heavier congeners just lookalikes?

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12154-12158

  Kapp, Jürgen ^a   Schreiner, Peter R ^a,b   Schleyer, Paul V R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; IONIZATION;

EID: 0030470054     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962275d     Document Type: Article

References (68)

1. (a) Trinquier, G. J. Am. Chem. Soc. 1992, 114, 6807.
2. (b) Trinquier, G. J. Chem. Soc., Faraday Trans. 1993, 59, 775.
3. (c) Palágyi, Z.; Schaefer, H. F.; Kapuy, E. J. Am. Chem. Soc. 1993, 115, 6901.
4. (d) Trinquier, G.; Malrieu, J.-P. J. Am. Chem. Soc. 1991, 113, 8634.
5. (e) Trinquier, G. J. Am. Chem. Soc. 1991, 113, 144.
6. (a) Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, Suppl 1.
7. (b) Olah, G. A., Schleyer, P. v. R, Eds. Carbonium Ions; Wiley: New York, 1976; Vols. I-V.
8. (c) Vogel, P. Carbocation Chemistry; Elsevier: Amsterdam, 1985.
9. (d) Hanack, M., Ed. Houben-Weyl, Methoden der Organischen Chemie; Thieme: Stuttgart, 1990; Vol. E19c.
10. (e) Saunders, M.; Jiménez-Väzquez, H. A. Chem. Rev. 1991, 91, 375.
11. (a) Hu, C.-H.; Shen, M.; Schaefer, H. F. Chem. Phys. Lett. 1992, 190, 543.
12. (b) Hu, C.-H.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer; H. F. J. Phys. Chem. 1994, 98, 5040 and references cited therein.
13. Lucas, D. J.; Curtiss, L. A.; Pople, J. A. J. Chem. Phys. 1993, 99, 6697 and references therein.
14. (a) Rashavachari, K. J. Chem. Phys. 1991, 95, 7373.
15. (b) Raghavachari, K. J. Chem. Phys. Ibid. 1992, 96, 4440.
16. (a) Schreiner, P. R.; Schaefer, H. F.; Schleyer, P. v. R. Group IV Cation Dihydrogen Gas Phase Complexes and Their Neutral Analogs. Theoretical Considerations. In Advances in Gas Phase Ion Chemistry; Adams, N., Babcock, L. M., Eds.; JAI Press Inc.: London, England, 1996; Vol. 2.
17. (b) Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. J. Chem. Phys. 1994, 101, 2141.
18. (c) Archibong, E. F.; Schreiner, P. R.; Leszcynski, J.; Schleyer, P.v. R.; Schaefer, H. F.; Sullivan, R. J. Chem. Phys. 1995, 102, 3667.
19. (a) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988.
20. (b) Huheey, J. E. Inorganic Chemistry, 3rd ed.; Harper: Cambridge, MA, 1983.
21. (c) Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Pergamon Press: Oxford, 1984.
22. (a) Gordon, M. S.; Gano, D. R.; Binkley, J. S.; Frisch, M. J. J. Am. Chem. Soc. 1986, 108, 2191.
23. (b) Su, M.-D.; Schlegel, H. B. J. Phys. Chem. 1993, 97, 9981.
24. (c) Nachtigall, P.; Jordan, K. D.; Smith, A.; Jónsson, H. J. Chem. Phys. 1996, 104, 148.
25. Raghavachari, K.; Whiteside, R. A.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1981, 103, 5649.
26. (a) Decke, A. D. Phys. Rev. 1988, A38, 3098.
27. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
28. GAUSSIAN94: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R., Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc., Pittsburgh, PA, 1995.
29. Hehre, W. J.; Radom, L.; Schleyer, P. v. R; Pople, J. A. Ab Initio Molecular Orbital Theory; J. Wiley & Sons: New York, 1986.
30. (a) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
31. (b) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
32. (c) Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem: Phys. 1984, 80, 3265.
33. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431.
34. d-polarization functions from Huzinaga, S., Ed. Gaussian Basis Sets for Molecular Calculations; Elsevier: New York, 1984.
35. (a) Cizek, J. Adv. Chem. Phys. 1969, 14, 35.
36. (b) Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910.
37. (c) Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359.
38. (d) Bartlett, R. J. J. Phys. Chem. 1989, 93, 1697.
39. (e) Scheiner, A. C.; Scuseria, G. E.; Rice, J. E.; Lee, T. J.; Schaefer, H. F. J. Chem. Phys. 1987, 87, 5361.
40. (a) Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479.
41. (b) Bartlett, R. J.; Watts, J. D.; Kucharski, S. A.; Noga, J. Chem. Phys. Lett. 1990, 165, 513.
42. (c) Scuseria, G. E. Chem. Phys. Lett. 1991, 176, 27.
43. p(H) = 1.50, 0.375. McLean, A. D.; Chandler, D. S. J. Chem. Phys. 1980, 72, 5639.
44. (a) Schwerdtfeger, P.; Heath, G. A.; Dolg, M.; Bennett, M. A. J. Am. Chem. Soc. 1992, 114, 7518.
45. (b) Kaupp, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1993, 115, 1061.
46. (c) Wang, S. G.; Schwarz, W. H. E. J. Mol. Struct. 1995, 338, 347.
47. Küchle, W.; Dolg, M.; Stoll, H.; Preuss, H. Mol. Phys. 1991, 74, 1245.
48. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
49. (b) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
50. (c) Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
51. (d) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
52. Kapp, J.; Remko, M. Schleyer, P.v.R. J. Am. Chem. Soc. 1996, 118, 5745.
53. Suggested Becke3LYP frequency scaling factor: 0.98. See: (a) Bauschlicher, C. W.; Partridge, H. J. Chem. Phys. 1995, 103, 1788.
54. (b) Urban, J.; Schreiner, P. R.; Vacek, G.; Schleyer, P. v. R.; Huang, J.; Leszezynski, J. Chem. Phys. Lett., in press.
55. 2 ligand, respectively.
56. Cremer, D.; Svensson, P.; Kraka, E.; Ahlberg, P. J. Am. Chem. Soc. 1993, 115, 7445.
57. Heidrich, D.; Kliesch, W.; Quapp, W. Properties of Chemically Interesting Potential Energy Surfaces; Springer-Verlag: Berlin, 1991; p 117.
58. Note, however, that orthogonal trajectories (as used in the IRC algorithm) may not be suitable as reaction path models for the description of bifurcations: Valtazanos, P.; Ruedenberg, K. Theor. Chim. Acta 1986, 69, 281.
59. For a recent discussion on determing bifurcation reaction paths, see: Taketsugu, T.; Tajima,N.; Hirao, K. J. Chem. Phys. 1996, 105, 1933.
60. (a) Caldwell, N. J.; Rice, J. K.; Nelson, H. H.; Adams, G. F.; Page, M. J. Chem. Phys. 1990, 93, 479.
61. (b) Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. Unpublished results.
62. Brooks, B. R., Schaefer, H. F. J. Chem. Phys. 1977, 67, 5146.
63. Gordon, M. S.; Xie, Y.; Yamaguchi, Y.; Grev, R. S.; Schaefer, H. F. J. Am. Chem. Soc. 1993, 115, 1503.
64. Moffat, H. K.; Jensen, K. F.; Carr, R. W. J. Phys. Chem. 1992, 96, 7695.
65. 4 species see: Hein, T. A.; Thiel, W.; Lee, T. J. J. Phys. Chem. 1993, 97, 4381.
66. For the effects of relativity on lead-hydrogen compounds see: (a) Dyall, K. G. J. Chem. Phys. 1992, 96, 1210.
67. (b) Dolg, M.; Küchle, W.; Stoll, H.; Schwerdtfeger, P. Mol. Phys. 1991, 74, 1265.
68. (c) Schwerdtfeger, P.; Silberbach, H.; Miehlich, B. J. Chem. Phys. 1989, 90, 762.