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Reviews of Chemical Intermediates

, Volume 9, Issue 2, pp 141–169 | Cite as

Theoretical aspects of carbodications

  • Koop Lammertsma
Article

Keywords

Potential Energy Surface Propylidene Aromatic Stabilization Bridgehead Carbon Carbocation Center 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    For early reviews, see: G.A. Olah, Chem. Eng. News, 45(1967)76; Science, 168(1970)1298; Angew. Chem. Int Ed. Engl., 12(1973)173; Top. Curr. Chem., 80(1979)21; Chem. Scr., 18(1981)97.Google Scholar
  2. 2.
    The search for observable long-lived cations was steered by early kinetic, stereochemical, product studies, and the development of superacid systems. Leading investigators that contributed fundamentally to these early developments include Bartlett, Hughes, Gillespie, Ingold, Meerwein, Nenitzescu, Whitmore, Winstein, and many others. Numerous compilations of these early studies have been made. For reasons of brevity we refer to the single comprehensive general review, G.A. Olah and P.v.R. Schleyer (Eds.), Carbonium Ions, Wiley, London, Vol. I, 1968; Vol. II, 1970; Vol. III, 1972; Vol. IV, 1973; and Vol. V, 1976.Google Scholar
  3. 3.
    For recent reviews, see: G.A. Olah, G.K.S. Prakash, and J. Sommer, Superacids, Wiley, New York, N.Y., 1985, Ch. 3; G.A. Olah, G.K.S. Prakash, R.E. Williams, L.D. Field, and K. Wade, Hypercarbon Chemistry, Wiley, New York, N.Y., 1987; P. Vogel, Carbocation Chemistry, Studies in Organic Chemistry 21, Elsevier, Amsterdam, The Netherlands, 1985.Google Scholar
  4. 4.
    M. Saundrs, J. Chandrasekhar, and P.v.R. Schleyer in P. de Mayo (Ed.), Rearrangements in Ground and Excited States, Vol. 1, Academic Press, New York, 1980, Ch. 1.Google Scholar
  5. 5.
    M. Schindler, J. Am. Chem. Soc., 109(1987)1020.CrossRefGoogle Scholar
  6. 6.
    J.M. Bollinger, C.A. Cupas, K.J. Friday, M.L. Woolfe, and G.A. Olah, J. Am. Chem. Soc., 89(1976)156; G.A. Olah, J.M. Bollinger, and A.M. White,ibid., J. Am. Chem. Soc., 91(1969)3667.CrossRefGoogle Scholar
  7. 7.
    For recent comprehensive reviews, see: G.K.S. Prakash, T.N. Tarik, and G.A. Olah, Angew. Chem. Int. Ed. Engl., 22(1983)390; R.M. Pagni, Tetrahedron, 40(1984)4161; P.v.R. Schleyer, Adv. Mass. Spectrom. A(1986)287.CrossRefGoogle Scholar
  8. 8.
    T. Ast, Adv. Mass. Spectrom., 8A(1980)555; M.R. Rabrenovi'c, C.J. Proctor, T. Ast, C.G. Herbert, A.G. Brenton, and J.H. Beynon, J. Phys. Chem., 87(1983)3305; W. Koch, F. Macquin, D. Stahl, and H. Schwarz, Chimia, 39(1985)376.Google Scholar
  9. 9.
    M. Guilhaus, A.G. Brenton, J.H. Beynon, M. Rabrenovi'c, and P.v.R. Schleyer, J. Phys. B: Atom. Mol. Phys., 17(1984)L605;Idem. M. Muilhaus, A.G. Brenton, J.H. Beynon, M. Rabrenovi'c, and P.v.R. Schleyer, J. Chem. Soc. Chem. Commun., (1985)210.CrossRefGoogle Scholar
  10. 10.
    H. Yagisawa, H. Sato, and T. Watanabe, Phys. Rev., Sect. A, 16(1977)1352.CrossRefGoogle Scholar
  11. 11.
    K. Raghavachari, R.A. Whiteside, J.A. Pople, and P.v.R. Schleyer, J. Am. Chem. Soc., 103(1981)5649; V. Dyczmons, V. Staemmler, and W. Kutzelnig, Chem. Phys. Lett., 5(1970)361.CrossRefGoogle Scholar
  12. 12.
    G.A. Olah, G. Klopman, and R.H. Schlosberg, J. Am. Chem. Soc., 91(1969)3261.CrossRefGoogle Scholar
  13. 13.
    See for example: C.A. Grob, Acc. Chem. Res., 16(1983)426; H.C. Brown,ibid., Acc. Chem. Res., 16(1983)432; G.A. Olah, G.K.S. Prakash, M. Saunder,ibid., Acc. Chem. Res., 16(1983)440; C. Walling,ibid., Acc. Chem. Res., 16(1983)448; H.C. Brown with comments by P.v.R. Schleyer, The Nonclassical Ion Problem, Plenum, New York, 1977.CrossRefGoogle Scholar
  14. 14.
    For an excellent review on quantum mechanical methodology and numerous detailed examples and reviews, see: W.J. Hehre, L. Radom, P.v.R. Schleyer, and J.A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, N.Y., 1986.Google Scholar
  15. 15.
    J.A. Pople, B. Tidor, and P.v.R. Schleyer, Chem. Phys. Lett., 88(1982)439.CrossRefGoogle Scholar
  16. 16.
    P.E.M. Siegbahn, Chem. Phys., 66(1982)443.CrossRefGoogle Scholar
  17. 17.
    K. Lammertsma, G.A. Olah, M. Barzaghi, and M. Simonetta, J. Am. Chem. Soc., 104(1982)6851.CrossRefGoogle Scholar
  18. 18.
    K. Lammertsma, M. Barzaghi, G.A. Olah, J.A. Pople, P.v.R. Schleyer, and M. Simonetta, J. Am. Chem. Soc., 105(1983)5258.CrossRefGoogle Scholar
  19. 19.
    K. Hiraoka and P. Kebarle, J. Am. Chem. Soc., 98(1976)6119.CrossRefGoogle Scholar
  20. 20.
    G.A. Olah, J.D. Felberg, and K. Lammertsma, J. Am. Chem. Soc., 105(1983)6529.CrossRefGoogle Scholar
  21. 21.
    R.N. Nobes, M.W. Wong, and L. Radom, Chem. Phys. Lett., 136(1987)299.CrossRefGoogle Scholar
  22. 22.
    K. Lammertsma, unpublished results.Google Scholar
  23. 23.
    M.W. Wong, B.F. Yates, R.H. Nobes, and L. Radom, J. Am. Chem. Soc., 109(1987)3181.CrossRefGoogle Scholar
  24. 24.
    T. Clark and R. Weiss, J. Org. Chem., 45(1980)1790.CrossRefGoogle Scholar
  25. 25.
    K. Lammertsma and P.v.R. Schleyer, J. Phys. Chem., in print.Google Scholar
  26. 26.
    J.A. Pople, M.J. Frisch, K. Raghavachari, and P.v.R. Schleyer, J. Comput. Chem., 3(1982)468.CrossRefGoogle Scholar
  27. 27.
    K. Lammertsma, M. Barzaghi, G.A. Olah, J.A. Pople, A.J. Kos, and P.v.R. Schleyer, J. Am. Chem. Soc., 105(1983)5252.CrossRefGoogle Scholar
  28. 28.
    M.J.S. Dewar and C.H. Reynolds, Theochem., 136(1986)209.CrossRefGoogle Scholar
  29. 29.
    G.A. Olah and M. Simonetta, J. Am. Chem. Soc., 104(1982)330.CrossRefGoogle Scholar
  30. 30.
    P.v.R. Schleyer, A.J. Kos, J.A. Pople, and A.T. Balaban, J. Am. Chem. Soc., 104(1982)3771.CrossRefGoogle Scholar
  31. 31.
    K. Lammertsma, J. Am. Chem. Soc., 106(1984)4619.CrossRefGoogle Scholar
  32. 32.
    W. Koch, G. Frenking, J. Gauss, and D. Cremer, J. Am. Chem. Soc., 108(1986)5808.CrossRefGoogle Scholar
  33. 33.
    B.F. Yates, W.J. Bouma, and L. Radom, J. Am. Chem. Soc., 108(1986)6545.CrossRefGoogle Scholar
  34. 34.
    R.A. Whiteside, M.J. Frisch, and J.A. Pople, Carnegie-Mellon Quantum Chemistry Archive, 3rd Edition, Carnegie-Mellon University, Pittsburgh, PA, 1983.Google Scholar
  35. 35.
    R.R. Mohr and W.N. Lipscomb, Inorg. Chem., 25(1986)1053.CrossRefGoogle Scholar
  36. 36.
    S.G. Shore, S.H. Lawrence, M.I. Watkins, and R. Bau, J. Am. Chem. Soc., 104(1982)7669.CrossRefGoogle Scholar
  37. 37.
    K. Raghavachari, P.v.R. Schleyer, and G.W. Spitznagel, J. Am. Chem. Soc., 105(1983)5917.CrossRefGoogle Scholar
  38. 38.
    G.C. Shields and T.F. Moran, Theor. Chim. Acta, 69(1986)147; J.R. Appling and T.F. Moran, Chem. Phys. Lett., 118(1985)188; J.R. Appling, G.S. Shields, and T.F. Moran, Org. Mass Spectrom., 21(1986)69; G.W. Burdick, G.C. Shields, J.R. Appling, and T.F. Moran, Int. J. Mass Spectrom. Ion Processes, 64(1985)315.CrossRefGoogle Scholar
  39. 39.
    M.W. Gill and L. Radom, Chem. Phys. Lett., 136(1987)294.CrossRefGoogle Scholar
  40. 40.
    K. Lammertsma, J.A. Pople, and P.v.R. Schleyer, J. Am. Chem. Soc., 108(1986)7;Idem., K. Lammertsma, J.A. Pople, and P.v.R. Schleyer, Theochem., 138(1986)183.CrossRefGoogle Scholar
  41. 41.
    R.A. Whiteside, R. Krishnan, D.J. DeFrees, J.A. Pople, and P.v.R. Schleyer, Chem. Phys. Lett., 78(1981)538.CrossRefGoogle Scholar
  42. 42.
    K. Lammertsma, J. Am. Chem. Soc., 108(1986)5127.CrossRefGoogle Scholar
  43. 43.a)
    D. Feller and E.R. Davidson, J. Am. Chem. Soc., 109(1987)4133; b) J.E. Jackson and L.E. Allen,ibid., J. Am. Chem. Soc., 106(1984)591; c) K.B. Wiberg and F.H. Walker,ibid., J. Am. Chem. Soc., 104(1982)5239; d) K.B. Wiberg, W.P. Dailey, F.H. Walker, S.T. Waddell, L.S. Crocker, and M. Newton,ibid., J. Am. Chem. Soc., 107(1985)7247; K. B. Wiberg, R.F.W. Bader, and C.D.H. Lau, J. Am. Chem. Soc., 109(1987)985, 1001.CrossRefGoogle Scholar
  44. 44.
    P.v.R. Schleyer and K. Lammertsma, unpublished results.Google Scholar
  45. 45.
    J. Chandrasekhar, P.v.R. Schleyer, and K.J. Krogh-Jespersen, Comput. Chem., 2(1981)356.CrossRefGoogle Scholar
  46. 46.
    K. Krogh-Jespersen, P.v.R. Schleyer, J.A. Pople, and D. Cremer, J. Am. Chem. Soc., 100(1978)4301; G.A. Olah and J.S. Staral, J. Am. Chem. Soc., 98(1976)6290; G.A. Olah and J.M. Bollinger,ibid., J. Am. Chem. Soc., 91(1969)3667; G.A. Olah and G.D. Mateescu,ibid., J. Am. Chem. Soc., 92(1970)1430; G.A. Olah, J.S. Staral, R.J. Spear, and G. Liang,ibid., J. Am. Chem. Soc., 97(1975)5849.CrossRefGoogle Scholar
  47. 47.
    K. Krogh-Jespersen, D. Cremer, J.D. Dill, J.A. Pople, and P.v.R. Schleyer, J. Am Chem. Soc., 103(1981)2589; P.H.M. Budzelaar, K. Krogh-Jespersen, T. Clark, and P.v.R. Schleyer,ibid., J. Am. Chem. Soc., 107(1985)2773; S.M. van der Kerk, P.M.H. Budzelaar, A. van der Kerk-van Hoof, G.J.M. van der Kerk, and P.v.R. Schleyer, Angew. Chem. Int. Ed. Engl., 22(1983)48; R. Wehrmann, C. Pues, H. Klusik, and A. Berndt,ibid., Angew. Chem. Int. Ed. Engl., 23(1984)372; C. Hildenbrandt, H. Pritzkow, U. Zenneck, and W. Siebert,ibid., Angew. Chem. Int. Ed. Engl., 23(1984)373.CrossRefGoogle Scholar
  48. 48.
    K. Lammertsma and P.v.R. Schleyer, J. Am. Chem. Soc., 105(1983)1049.CrossRefGoogle Scholar
  49. 49.
    M.J.S. Dewar and M.K. Hooloway, J. Am. Chem. Soc., 106(1984)6619.CrossRefGoogle Scholar
  50. 50.
    T.W. Bentley and C.A. Wellington, Org. Mass Spectrom., 16(1981)523.CrossRefGoogle Scholar
  51. 51.
    H. Hogeveen and P.W. Kwant, Acc. Chem. Res., 8(1975)413;Idem., H. Hogeveen and P.W. Kwant, Tetrahedron Lett., (1973)1665;Idem., H. Hogeveen and P.W. Kwant, J. Am. Chem. Soc., 96(1974)2208; C. Giordano, R.F. Heldeweg, and H. Hoogeveen,ibid., J. Am. Chem. Soc., 99(1977)5181; H. Hogeveen and E.M.G.A. van Kruchten, J. Org. Chem., 46(1981)1350; H. Carnadi, C. Giordano, R.F. Heldeweg, H. Hogeveen, and E.M.G.A. van Kruchten, Israel J. Chem., 21(1981)229.CrossRefGoogle Scholar
  52. 52.
    H.T. Jonkman and W.C. Nieuwpoort, Tetrahedron Lett., (1973)1671.Google Scholar
  53. 53.
    E.D. Jemmis and P.v.R. Schleyer, J. Am. Chem. Soc., 104(1982)4781.CrossRefGoogle Scholar
  54. 54.
    G.A. Olah, G. Liang, P.v.R. Schleyer, E.M. Engler, M.J.S. Dewar, and R.C. Bingham, J. Am. Chem. Soc., 95(1973)6829; A. de Meijere, O. Schallner, P. Gölitz, W. Weber, P.v.R. Schleyer, G.K.S. Prakash, and G.A. Olah, J. Org. Chem., 50(1985)5255.CrossRefGoogle Scholar
  55. 55.
    G.A. Olah, G. Liang, P.v.R. Schleyer, W. Parker, and C.I.F. Watt, J. Am. Chem. Soc., 99(1977)966.CrossRefGoogle Scholar
  56. 56.
    K. Lammertsma and H. Cerfontain, J. Am. Chem. Soc., 102(1980)3257.CrossRefGoogle Scholar
  57. 57.
    P. Gund, J. Chem. Educ., 49(1972)100.CrossRefGoogle Scholar
  58. 58.
    T. Clark, D. Wilhelm, and P.v.R. Schleyer, Tetrahedron Lett. (1982)3257.Google Scholar
  59. 59.
    K. Schötz, T. Clark, H. Schaller, and P.v.R. Schleyer, J. Org. Chem., 49(1984)733.CrossRefGoogle Scholar
  60. 60.
    G.K.S. Prakash, V.V. Krishnamurthy, R. Herges, R. Bau, H. Yuan, G.A. Olah, W.-D. Fessner, and H. Prinzbach, J. Am. Chem. Soc., 108(1986)836.CrossRefGoogle Scholar
  61. 61.
    W.-D. Fessner, G. Sedelmeier, P.R. Spurr, G. Rihs, and H. Prinzbach J. Am. Chem. Soc., 109(1987)4626.CrossRefGoogle Scholar
  62. 62.
    M. Bremer, P.v.R. Schleyer, K. Schoetz, M. Kausch, and M. Schindler, Angew. Chem. Int. Ed. Engl., 26(1987)761.CrossRefGoogle Scholar
  63. 63.
    G.A. Olah, G.K.S. Prakash, J.G. Shih, V.V. Krishnamurthy, G.D. Mateescu, G. Liang, G. Sipos, V. Buss, T.M. Gund, and P.v.R. Schleyer, J. Am. Chem. Soc., 107(1985)2764.CrossRefGoogle Scholar
  64. 64.
    G.K.S. Prakash, M. Farnia, S. Keyanian, G.A. Olah, H.J. Kuhn, and K. Schaffner, J. Am. Chem. Soc., 109(1987)911.CrossRefGoogle Scholar

Copyright information

© Springer 1988

Authors and Affiliations

  • Koop Lammertsma
    • 1
  1. 1.Department of ChemistryUniversity of Alabama at BirminghamBirminghamU.S.A.

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