Conformations of [10]annulene: More bad news for density functional theory and second-order perturbation theory

Journal of the American Chemical Society

Volumn 121, Issue 46, 1999, Pages 10788-10793

  King, Rollin A ^a   Crawford, T Daniel ^b   Stanton, John F ^b   Schaefer III, Henry F ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CONFORMATIONAL TRANSITION; ENERGY TRANSFER; ENTHALPY; ENTROPY; THEORY;

EID: 0033601062     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991429x     Document Type: Article

References (48)

1. Hückel, E. Z. Phys. 1931, 70, 204.
2. Burkoth, T. L.; van Tamelen, E. E. In Nonbenzenoid Aromatics; Snyder, J. P., Ed.; Academic Press: New York, 1969; Vol. 1, Chapter 3, p 63.
3. Sondheimer, F.; Wolovsky, R. Tetrahedron Lett. 1959, 3, 3.
4. Sondheimer, F.; Calder, I. C.; Elix, J. A.; Gaoni, U.; Garrett, P. J.; Grohmann, K.; diMaio, G.; Mayer, J.; Sargent, M. V.; Wolovsky, R. Chem. Soc., Spec. Publ. 1967, 21, 15.
5. van Tamelen, E. E.; Burkoth, T. L. J. Am. Chem. Soc. 1967, 89, 151.
6. Masamune, S.; Seidner, R. T. J. Chem. Soc., Chem. Commun. 1969, 542.
7. Masamune, S.; Hojo, K.; Bigam, G.; Rabenstein, D. L. J. Am. Chem. Soc. 1971, 93, 4966.
8. Kleier, D. A.; Dixon, D. A.; Lipscomb, W. N. Theor. Chim. Acta 1975, 40, 33.
9. Haddon, R. C; Raghavachari, K. J. Am. Chem. Soc. 1982, 104, 3516.
10. Haddon, R. C.; Raghavachari, K. J. Am. Chem. Soc. 1985, 107, 289.
11. Baird, N. C. J. Am. Chem. Soc. 1972, 94, 4941.
12. Aihara, J. J. Am. Chem. Soc. 1976, 98, 2750.
13. Haddon, R. C. J. Am. Chem. Soc. 1979, 101, 1722.
14. Baumann, H. J. Am. Chem. Soc. 1978, 100, 7196.
15. Sulzbach, H. M.; Schleyer, P. R.; Jiao, H.; Xie, Y.; Schaefer, H. F. J. Am. Chem. Soc. 1995, 117, 1369.
16. Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133.
17. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
18. Sulzbach, H. M.; Schaefer, H. F.; Klopper, W.; Luthi, H. P. J. Am. Chem. Soc. 1996, 118, 3519.
19. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
20. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910.
21. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479.
22. Thomas, J. R.; DeLeeuw, B. J.; Vacek, G.; Crawford, T. D.; Yamaguchi, Y.; Schaefer, H. F. J. Chem. Phys. 1993, 99, 403.
23. Lee, T. J.; Scuseria, G. E. In Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy; Langhoff, S. R., Ed.; Kluwer Academic Publishers: Dordrecht, 1995; pp 47-108.
24. Huzinaga, S. J. Chem. Phys. 1965, 42, 1293.
25. Dunning, T. H. J. Chem. Phys. 1970, 53, 2823.
26. Dunning, T. H. J. Chem. Phys. 1971, 55, 716.
27. Stanton, J. F.; Gauss, J.; Watts, J. D.; Lauderdale, W. J.; Bartlett, R. J. ACES II. The package also contains modified versions of the MOLECULE Gaussian integral program of J. Almlöf and P. R. Taylor, the ABACUS integral derivative program written by T. U. Helgaker, H. J. Aa. Jensen, P. Jørgensen, and P. R. Taylor, and the PROPS property evaluation integral code of P. R. Taylor.
28. Stanton, J. F.; Gauss, J.; Watts, J. D.; Lauderdale, W. J.; Bartlett, R. J. ACES II. The package also contains modified versions of the MOLECULE Gaussian integral program of J. Almlöf and P. R. Taylor, the ABACUS integral derivative program written by T. U. Helgaker, H. J. Aa. Jensen, P. Jørgensen, and P. R. Taylor, and the PROPS property evaluation integral code of P. R. Taylor.
29. Stanton, J. F.; Gauss, J.; Watts, J. D.; Lauderdale, W. J.; Bartlett, R. J. ACES II. The package also contains modified versions of the MOLECULE Gaussian integral program of J. Almlöf and P. R. Taylor, the ABACUS integral derivative program written by T. U. Helgaker, H. J. Aa. Jensen, P. Jørgensen, and P. R. Taylor, and the PROPS property evaluation integral code of P. R. Taylor.
30. Stanton, J. F.; Gauss, J.; Watts, J. D.; Lauderdale, W. J.; Bartlett, R. J. ACES II. The package also contains modified versions of the MOLECULE Gaussian integral program of J. Almlöf and P. R. Taylor, the ABACUS integral derivative program written by T. U. Helgaker, H. J. Aa. Jensen, P. Jørgensen, and P. R. Taylor, and the PROPS property evaluation integral code of P. R. Taylor.
31. Scheiner, A. C.; Scuseria, G. E.; Rice, J. E.; Lee, T. J.; Schaefer, H. F. J. Chem. Phys. 1987, 87, 5351.
32. Scuseria, G. E. J. Chem. Phys. 1991, 94, 442.
33. 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 94, Revision C.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
34. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
35. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785.
36. Perdew, J. P. Phys. Rev. B. 1986, 33, 8822.
37. Xie, Y.; Schaefer, H. F.; Liang, G.; Bowen, J. P. J. Am. Chem. Soc. 1994, 116, 1442.
38. 40-42 in terms of π-orbital axis vector (POAV) misalignment for many related conjugated organic moecules. The POAV analysis could be useful as a quantitative measure of this phenomenon in [10]annulene isomers as well.
39. Tai, J. C.; Allinger, N. L. J. Comp. Chem. 1998, 19, 475.
40. Bettinger, H. F.; Sulzbach, H. M.; Schleyer, P. R.; Schaefer, H. F. J. Chem. Phys. 1999, 110, submitted for publication.
41. Watts, J. D.; Bartlett, R. J. Chem. Phys. Lett. 1992, 190, 19.
42. Choi, C. H.; Kertesz, M. J. Phys. Chem. A 1998, 102, 3429.
43. Haddon, R. C. J. Am. Chem. Soc. 1986, 108, 2837.
44. Haddon, R. C. Acc. Chem. Res. 1988, 21, 243.
45. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385.
46. Leška, J.; Loos, D. J. J. Mol. Struct. 1974, 21, 245.
47. Loos, D.; Leška, J. J. Collect. Czech. Chem. Commun. 1980, 45, 187.
48. Farnell, L.; Kao, J.; Radom, L.; Schaefer, H. F. J. Am. Chem. Soc. 1981, 103, 2147.