Empirical force-field and ab initio calculations on delocalized open chain cations

Journal of Computational Chemistry

Volumn 18, Issue 1, 1997, Pages 28-44

  Reindl, Bernd ^a   Clark, Timothy ^a   Schleyer, Paul Von R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345189796     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(19970115)18:1<28::AID-JCC4>3.0.CO;2-1     Document Type: Article

References (54)

1. For a review see P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985.
2. G. J. Gleicher and P. v. R. Schleyer, J. Am. Chem. Soc., 89, 582 (1967).
3. A review is given by P. Müller and J. Mareda, in Cage Hydrocarbons, G. A. Olah, Ed., Wiley, New York, 1990, p. 189.
4. For early calculations see, for example: (a) J. L. Fry, E. M. Engler, and P. v. R. Schleyer, J. Am. Chem. Soc., 94, 4628 (1972) (b) R. C. Bingham and P. v. R. Schleyer, J. Am. Chem. Soc., 93, 3189 (1971) (c) R. C. Bingham, W. F. Sliwinski, and P. v. R. Schleyer, J. Am. Chem. Soc., 92, 3471 (1970).
5. For early calculations see, for example: (a) J. L. Fry, E. M. Engler, and P. v. R. Schleyer, J. Am. Chem. Soc., 94, 4628 (1972) (b) R. C. Bingham and P. v. R. Schleyer, J. Am. Chem. Soc., 93, 3189 (1971) (c) R. C. Bingham, W. F. Sliwinski, and P. v. R. Schleyer, J. Am. Chem. Soc., 92, 3471 (1970).
6. For early calculations see, for example: (a) J. L. Fry, E. M. Engler, and P. v. R. Schleyer, J. Am. Chem. Soc., 94, 4628 (1972) (b) R. C. Bingham and P. v. R. Schleyer, J. Am. Chem. Soc., 93, 3189 (1971) (c) R. C. Bingham, W. F. Sliwinski, and P. v. R. Schleyer, J. Am. Chem. Soc., 92, 3471 (1970).
7. (a) P. Müller, J. Mareda, and D. Milin, J. Phys. Org. Chem., 8, 507 (1995)
8. (b) P. Müller and M. Mareda, J. Comput. Chem., 10, 863 (1989)
9. (c) P. Müller, D. Milin, W. Q. Feng, R. Houriet, and E. W. Della, J. Am. Chem. Soc., 114, 6169 (1992)
10. (d) P. Müller and D. Milin, Helv. Chim. Acta, 74, 1808 (1991).
11. B. Reindl, T. Clark, and P. v. R. Schleyer, J. Comput. Chem. (in press).
12. J. T. Sprague, J. N. Tai, Y. Yuh, and N. L. Allinger, J. Comput. Chem., 8, 581 (1987). For a review see: U. Burkert and N. L. Allinger, Molecular Mechanics, American Chemical Society, Washington, DC, 1982.
13. J. T. Sprague, J. N. Tai, Y. Yuh, and N. L. Allinger, J. Comput. Chem., 8, 581 (1987). For a review see: U. Burkert and N. L. Allinger, Molecular Mechanics, American Chemical Society, Washington, DC, 1982.
14. B. Reindl and P. v. R. Schleyer, J. Comput Chem. (in press).
15. R. Kuhn and C. Grundmann, Chem. Berl., 71B, 442 (1938).
16. L. De Vries, J. Am. Chem. Soc., 83, 2392 (1961).
17. T. S. Sorensen, J. Am. Chem. Soc., 87, 5075 (1965).
18. D. N. Dashkevich and Y. Y. Tsmur, Zh. Obshch. Khim., 34, 1357 (1963).
19. T. S. Sorensen, in Carbonium Ions, Vol. 2, G. A. Olah and P. v. R. Schleyer, Eds., Plenum Press, New York, 1968, p. 807.
20. (a) J. Gauss, Chem. Phys. Lett., 191, 614 (1992)
21. (b) J. Gauss, J. Chem. Phys., 99, 3629 (1993).
22. P. Buzek, P. v. R. Schleyer, H. Vancik, Z. Mihalic, and J. Gauss, Angew. Chem. Int. Ed. Engl., 33, 448 (1994).
23. M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, P. J. Fox, D. J. De Frees, J. Baker, J. J. P. Stewart, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1992.
24. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 28, 213 (1973).
25. (a) C. Møller and M. S. Plesset, Phys. Rev. 46, 618 (1934)
26. (b) J. A. Pople, R. Seeger, and R. Krishnan, Int. J. Quant. Chem. Symp., 11, 149 (1977).
27. (a) W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1978, p. 163
28. (b) P. v. R. Schleyer, H. Jiao, R. M. Glukhovtsev, and E. Kraka, J. Am. Chem. Soc., 116, 10229 (1994)
29. (c) H. M. Sulzbach, P. v. R. Schleyer, H. Jiao, and H. F. Schaefer III, J. Am. Chem. Soc., 117, 1369 (1995).
30. (a) R. Krishnan and J. A. Pople, Int. J. Quant. Chem., 14, 91 (1978)
31. (b) R. Krishnan, M. J. Frisch, and J. A. Pople, J. Chem. Phys., 72, 4244 (1980).
32. (a) J. P. Forster and F. Weinhold, J. Am. Chem. Soc., 102, 7211 (1980)
33. (b) A. E. Reed and F. Weinhold, J. Chem. Phys., 78, 4066 (1983)
34. (c) A. E. Reed, R. B. Weinstock, and F. Weinhold, J. Chem. Phys., 83, 735 (1985)
35. (d) J. E. Carpenter and F. Weinhold, J. Mol. Struct. (Theochem), 41, 169 (1988)
36. (e) A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev., 88, 899 (1988).
37. The program is available from the Quantum Chemistry Program Exchange (University of Indiana, Bloomington, IN 47405) and from Molecular Design Ltd., 2132 Fallaron Drive, San Leandro, CA 94577.
38. E. A. Kallel and K. Houk, J. Org. Chem., 54, 6006 (1989).
39. P. v. R. Schleyer, J. Am. Chem. Soc., 107, 4793 (1985).
40. G. A. Olah and M. B. Comisarow, J. Am. Chem. Soc., 86, 5682 (1964).
41. T. Truong, M. S. Gordon, and P. Boudjouk, Organometallics, 3, 484 (1984).
42. (a) Y. Apeloig and P. v. R. Schleyer, Tetrahedron Lett., 18, 464 (1977)
43. (b) Y. Apeloig, S. A. Godleski, D. J. Heacock, and J. M. McKelvey, Tetrahedron Lett., 23, 3297 (1981).
44. (a) T. S. Sorensen, Can. J. Chem., 42, 2768 (1964)
45. (b) T. S. Sorensen, Can. J. Chem., 43, 2744 (1965).
46. P. v. R. Schleyer, J. D. Dill, J. A. Pople, and W. J. Hehre, Tetrahedron, 33, 2497 (1977).
47. K. B. Wiberg, J. R. Cheeseman, J. W. Ochterski, and M. J. Frisch, J. Am. Chem. Soc., 117, 6535 (1995).
48. P. Wolkoff, J. L. Holmes, and F. F. Lossing, Adv. Mass Spect., 8A, 743 (1980).
49. (a) A. Maccoll, Org. Mass. Spect., 17, 1 (1982)
50. (b) J. C. Traeger, Int. J. Mass Spect. Ion Proc., 58, 259 (1984).
51. J. C. Schultz, F. A. Houle, and J. L. Beauchamp, J. Am. Chem. Soc., 106, 7336 (1984).
52. J. C. Traeger and R. G. McLoughlin, J. Am. Chem. Soc., 103, 3647 (1981).
53. Experimental data from S. G. Lias, J. E. Bartmess, J. F. Liebman, J. L. Holmes, R. D. Levin, and W. G. Mallard, J. Phys. Chem. Rev. Data, 17 (Suppl. 1) (1988).
54. D. H. Aue and M. T. Bowers, in Gas Phase Ion Chemistry, Vol. 2, M. T. Bowers, Ed., Academic Press, New York, 1979, Chapter 9.