Bond length alternation and aromaticity in large annulenes

Journal of Chemical Physics

Volumn 108, Issue 16, 1998, Pages 6681-6688

  Choi, Cheol Ho ^a   Kertesz, Miklos ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001561373     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.476083     Document Type: Article

References (63)

1. E. Hückel, Z. Phys. 70, 204 (1931); 72, 310 (1931); 76, 628 (1932).
2. E. Hückel, Z. Phys. 70, 204 (1931); 72, 310 (1931); 76, 628 (1932).
3. E. Hückel, Z. Phys. 70, 204 (1931); 72, 310 (1931); 76, 628 (1932).
4. M. J. S. Dewar and R. C. Dougherty, The PMO Theory of Organic Chemistry (Plenum, New York, 1975).
5. H. A. Jahn and E. Teller, Proc. R. Soc. London, Ser. A 161, 220 (1937).
6. H. C. Longuet-Higgins and L. Salem, Proc. R. Soc. London, Ser. A 251, 172 (1959); L. Salem, Molecular Orbital Theory of Conjugated Systems (Benjamin, New York, 1966).
7. H. C. Longuet-Higgins and L. Salem, Proc. R. Soc. London, Ser. A 251, 172 (1959); L. Salem, Molecular Orbital Theory of Conjugated Systems (Benjamin, New York, 1966).
8. R. Peierls, Quantum Theory of Solids (Oxford University Press, New York, 1955).
9. A. A. Ovchinnikov, I. I. Ukrainskii, and G. F. Kventsel, Usp. Fiz. Nauk 108, 81 (1972); M. Kertesz, Adv. Quantum Chem. 15, 161 (1982); A. J. Heeger, S. Kivelson, J. R. Schrieffer, and W.-P. Su, Rev. Mod. Phys. 60, 781 (1988); J. W. Mintmire and C. T. White, Phys. Rev. B 35, 4180 (1987).
10. A. A. Ovchinnikov, I. I. Ukrainskii, and G. F. Kventsel, Usp. Fiz. Nauk 108, 81 (1972); M. Kertesz, Adv. Quantum Chem. 15, 161 (1982); A. J. Heeger, S. Kivelson, J. R. Schrieffer, and W.-P. Su, Rev. Mod. Phys. 60, 781 (1988); J. W. Mintmire and C. T. White, Phys. Rev. B 35, 4180 (1987).
11. A. A. Ovchinnikov, I. I. Ukrainskii, and G. F. Kventsel, Usp. Fiz. Nauk 108, 81 (1972); M. Kertesz, Adv. Quantum Chem. 15, 161 (1982); A. J. Heeger, S. Kivelson, J. R. Schrieffer, and W.-P. Su, Rev. Mod. Phys. 60, 781 (1988); J. W. Mintmire and C. T. White, Phys. Rev. B 35, 4180 (1987).
12. A. A. Ovchinnikov, I. I. Ukrainskii, and G. F. Kventsel, Usp. Fiz. Nauk 108, 81 (1972); M. Kertesz, Adv. Quantum Chem. 15, 161 (1982); A. J. Heeger, S. Kivelson, J. R. Schrieffer, and W.-P. Su, Rev. Mod. Phys. 60, 781 (1988); J. W. Mintmire and C. T. White, Phys. Rev. B 35, 4180 (1987).
13. C. H. Choi, M. Kertesz, and A. Karpfen, J. Chem. Phys. 107, 6712 (1997).
14. C. R. Fincher, Jr., C.-E. Chem, A. J. Heeger, and A. G. MacDiarmid, Phys. Rev. Lett. 48, 100 (1982); C. S. Yannoni and T. C. Clarke, Phys. Rev. Lett. 51, 1191 (1983); H. Kahlert, O. Leitner, and G. Leising, Synth. Met. 17, 467 (1987); Q. Zhu and J. E. Fisher, Solid State Commun. 83, 179 (1992).
15. C. R. Fincher, Jr., C.-E. Chem, A. J. Heeger, and A. G. MacDiarmid, Phys. Rev. Lett. 48, 100 (1982); C. S. Yannoni and T. C. Clarke, Phys. Rev. Lett. 51, 1191 (1983); H. Kahlert, O. Leitner, and G. Leising, Synth. Met. 17, 467 (1987); Q. Zhu and J. E. Fisher, Solid State Commun. 83, 179 (1992).
16. C. R. Fincher, Jr., C.-E. Chem, A. J. Heeger, and A. G. MacDiarmid, Phys. Rev. Lett. 48, 100 (1982); C. S. Yannoni and T. C. Clarke, Phys. Rev. Lett. 51, 1191 (1983); H. Kahlert, O. Leitner, and G. Leising, Synth. Met. 17, 467 (1987); Q. Zhu and J. E. Fisher, Solid State Commun. 83, 179 (1992).
17. C. R. Fincher, Jr., C.-E. Chem, A. J. Heeger, and A. G. MacDiarmid, Phys. Rev. Lett. 48, 100 (1982); C. S. Yannoni and T. C. Clarke, Phys. Rev. Lett. 51, 1191 (1983); H. Kahlert, O. Leitner, and G. Leising, Synth. Met. 17, 467 (1987); Q. Zhu and J. E. Fisher, Solid State Commun. 83, 179 (1992).
18. (a) P. C. Hiberty, D. Danovich, A. Shurki, and S. Shaik, J. Am. Chem. Soc. 117, 7760 (1995)
19. (b) Y. Haas and S. Zilberg, ibid. 117, 5387 (1995)
20. (c) S. Shaik, A. Shurki, D. Danovich, and P. C. Hiberty, ibid. 118, 666 (1996).
21. M. J. S. Dewar, R. C. Haddon, and P. J. Student, J. Chem. Soc. Chem. Commun. , 569 (1974).
22. M. J. S. Dewar and M. L. McKee, Pure Appl. Chem. 52, 1431 (1980).
23. R. C. Haddon and K. Raghavachari, J. Am. Chem. Soc. 107, 289 (1985).
24. K. Jug and E. Fasold, J. Am. Chem. Soc. 109, 2263 (1987).
25. G. Binsch, I. Tamir, and R. D. Hill, J. Am. Chem. Soc. 91, 2246 (1969).
26. K. Yoshizawa, T. Kato, and T. Yamabe, J. Phys. Chem. 100, 5697 (1996).
27. M. Takahashi and J. Paldus, Int. J. Quantum Chem. 26, 349 (1984)
28. (b) 28, 459 (1985)
29. (c) X. Z. Li and J. Paldus, ibid. 60, 513 (1996).
30. (a) H. Jiao and P. v. R. Schleyer, Angew. Chem. Int. Ed. Engl. 35, 2383 (1996)
31. (b) K. K. Baldridge and J. S. Siegel, ibid. 36, 745 (1997).
32. W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory (Wiley, New York, 1986).
33. C. H. Choi, M. Kertesz, and A. Karpfen, J. Am. Chem. Soc. 119, 11994 (1997).
34. R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules (Oxford University Press, Oxford, 1989).
35. F. Sondheimer, R. Wolovsky, and Y. Amiel, J. Am. Chem. Soc. 84, 274 (1962).
36. J. Bregman, F. L. Hirshfeld, D. Rabinovich, and G. M. J. Schmidt, Acta Crystallogr. 19, 227 (1965); C. C. Chiang and I. C. Paul, J. Am. Chem. Soc. 94, 4741 (1972); S. Gorter, E. Keulemans-Rutten, M. Krever, C. Romers, and D. W. J. Cruickshank, Acta Crystallogr. B 51, 1036 (1995).
37. J. Bregman, F. L. Hirshfeld, D. Rabinovich, and G. M. J. Schmidt, Acta Crystallogr. 19, 227 (1965); C. C. Chiang and I. C. Paul, J. Am. Chem. Soc. 94, 4741 (1972); S. Gorter, E. Keulemans-Rutten, M. Krever, C. Romers, and D. W. J. Cruickshank, Acta Crystallogr. B 51, 1036 (1995).
38. J. Bregman, F. L. Hirshfeld, D. Rabinovich, and G. M. J. Schmidt, Acta Crystallogr. 19, 227 (1965); C. C. Chiang and I. C. Paul, J. Am. Chem. Soc. 94, 4741 (1972); S. Gorter, E. Keulemans-Rutten, M. Krever, C. Romers, and D. W. J. Cruickshank, Acta Crystallogr. B 51, 1036 (1995).
39. (a) P. J. Garatt, Aromaticity (Wiley, New York, 1986)
40. (b) D. Lloyd, The Chemistry of Conjugated Cyclic Compounds (Wiley, New York, 1989)
41. (c) H. Vogler and G. Ege, Tetrahedron 32, 1789 (1976)
42. (d) J. R. M. Oth, H. Baumann, J.-M. Gilles, and G. Schröder, J. Am. Chem. Soc. 94, 3498 (1972)
43. (e) B. W. Metcalf and F. Sondheimer, ibid. 93, 6875 (1971)
44. (f) R. M. McQuilkin et al., J. Chem. Soc. A , 338 (1971)
45. (g) Jackman et al., J. Am. Chem. Soc. 84, 4307 (1962).
46. GAUSSIAN 94, 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. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, 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, Inc., Pittsburgh PA, 1995.
47. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988).
48. A. D. Becke, J. Chem. Phys. 98, 1372 (1993).
49. K. Wolinski, J. F. Hilton, and P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990).
50. S. Hirata, H. Torii, and M. Tasumi, J. Chem. Phys. 103, 8964 (1995).
51. M. J. S. Dewar and C. de Llano, J. Am. Chem. Soc. 91, 789 (1969).
52. (a) W. J. Hehre, R. Ditchfield, L. Radom, and J. A. Pople, J. Am. Chem. Soc. 92, 4796 (1970)
53. (b) P. George, M. Trachtman, C. W. Bock, and A. M. Brett, J. Chem. Soc. Perkin Trans. 2, 1222 (1976)
54. (c) P. George, M. Trachtman, A. M. Brett, and C. W. Bock, ibid. 2, 1036 (1977)
55. (d) B. A. Hess, Jr. and L. J. Schaad, J. Am. Chem. Soc. 93, 305 (1971)
56. (e) 105, 7500 (1983).
57. (a) P. George, M. Trachman, C. W. Bock, and A. M. Bret, J. Chem. Soc. Perkin Trans. 2, 1222 (1976).
58. H. Eckardt, J. Chem. Phys. 79, 2085 (1983); S. D. Phillips, R. Worland, G. Yu, T. Hagler, R. Freedman, Y. Cao, V. Yoon, J. Chiang, W. C. Walker, and A. J. Heeger, Phys. Rev. B 40, 9751 (1989).
59. H. Eckardt, J. Chem. Phys. 79, 2085 (1983); S. D. Phillips, R. Worland, G. Yu, T. Hagler, R. Freedman, Y. Cao, V. Yoon, J. Chiang, W. C. Walker, and A. J. Heeger, Phys. Rev. B 40, 9751 (1989).
60. M. Schluter and L. J. Sham, Adv. Quantum Chem. 21, 97 (1990).
61. W. P. Su, J. R. Schrieffer, and A. J. Heeger, Phys. Rev. Lett. 44, 1698 (1979).
62. (a) P. v. R. Schleyer and H. Jiao, Pure Appl. Chem. 68, 209 (1996)
63. (b) P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, and N. J. R. v. Eikema Hommes, J. Am. Chem. Soc. 118, 6317 (1996).