Heteroaromaticity. 13. Bond alternation and its consequences for conjugation energies and other criteria of aromaticity

Tetrahedron

Volumn 54, Issue 18, 1998, Pages 4641-4646

  Bird, Clive W ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE; INDAN DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CONJUGATION; ENERGY; PRIORITY JOURNAL; QUANTITATIVE DIAGNOSIS;

EID: 0032580352     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00180-X     Document Type: Article

References (34)

1. 1. Mills, W.H.; Nixon, I.G., J. Chem. Soc., 1930, 2510-2524.
2. 2. Badger, G.M., "The Structures and Reactions of the Aromatic Compounds", Cambridge University Press, Cambridge, 1954.
3. 3. Frank, N.L.; Siegel, J.S., Advances in Theoretically Interesting Molecules, 1995, 3, 209-260.
4. 4. Bird, C.W., Tetrahedron, 1997, 53, 13111-13118.
5. 5. Bird, C.W., Tetrahedron, 1997, 53, 17195-17200.
6. 6. Bird, C.W., Tetrahedron, 1985, 41, 1409-1414.
7. 7. Bird, C.W., Tetrahedron, 1986, 42, 89-92.
8. 8. Bird, C.W., Tetrahedron, 1992, 48, 335-340.
9. 9. Katritzky, A.R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc., 1989, 111, 7-15; Katritzky, A.R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M., J. Prakt. Chem., 1990, 332, 853-869; Katritzky, A.R.; Barczynski, P.; Szafran, M.; Feygelman, V.; Musumarra, G. ibid., 870-884; Katritzky, A.R.; Barczynski, P. ibid., 885-897; Katritzky, A.R.; Szafran, M.; Malhotra, N.; Chaudry, S.U.; Anders, E. Tetrahedron Comp. Meth., 1990, 3, 247-269.
10. 9. Katritzky, A.R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc., 1989, 111, 7-15; Katritzky, A.R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M., J. Prakt. Chem., 1990, 332, 853-869; Katritzky, A.R.; Barczynski, P.; Szafran, M.; Feygelman, V.; Musumarra, G. ibid., 870-884; Katritzky, A.R.; Barczynski, P. ibid., 885-897; Katritzky, A.R.; Szafran, M.; Malhotra, N.; Chaudry, S.U.; Anders, E. Tetrahedron Comp. Meth., 1990, 3, 247-269.
11. 9. Katritzky, A.R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc., 1989, 111, 7-15; Katritzky, A.R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M., J. Prakt. Chem., 1990, 332, 853-869; Katritzky, A.R.; Barczynski, P.; Szafran, M.; Feygelman, V.; Musumarra, G. ibid., 870-884; Katritzky, A.R.; Barczynski, P. ibid., 885-897; Katritzky, A.R.; Szafran, M.; Malhotra, N.; Chaudry, S.U.; Anders, E. Tetrahedron Comp. Meth., 1990, 3, 247-269.
12. 9. Katritzky, A.R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc., 1989, 111, 7-15; Katritzky, A.R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M., J. Prakt. Chem., 1990, 332, 853-869; Katritzky, A.R.; Barczynski, P.; Szafran, M.; Feygelman, V.; Musumarra, G. ibid., 870-884; Katritzky, A.R.; Barczynski, P. ibid., 885-897; Katritzky, A.R.; Szafran, M.; Malhotra, N.; Chaudry, S.U.; Anders, E. Tetrahedron Comp. Meth., 1990, 3, 247-269.
13. 9. Katritzky, A.R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc., 1989, 111, 7-15; Katritzky, A.R.; Feygelman, V.; Musumarra, G.; Barczynski, P.; Szafran, M., J. Prakt. Chem., 1990, 332, 853-869; Katritzky, A.R.; Barczynski, P.; Szafran, M.; Feygelman, V.; Musumarra, G. ibid., 870-884; Katritzky, A.R.; Barczynski, P. ibid., 885-897; Katritzky, A.R.; Szafran, M.; Malhotra, N.; Chaudry, S.U.; Anders, E. Tetrahedron Comp. Meth., 1990, 3, 247-269.
14. 10. Gordy, W., J. Chem. Phys., 1947, 15, 305-310.
15. 11. Dauben, H.J.; Osborne, A.G. Abstracts of the 130th National Meeting of the American Chemical Society, Atlantic City, N.J., 1956, p 37 -O. Trost, B.M.; Kinson, P.L.; Maier, C.A.; Paul, I.C. J. Am. Chem. Soc., 1971, 93, 7275-7282.
16. 11. Dauben, H.J.; Osborne, A.G. Abstracts of the 130th National Meeting of the American Chemical Society, Atlantic City, N.J., 1956, p 37 -O. Trost, B.M.; Kinson, P.L.; Maier, C.A.; Paul, I.C. J. Am. Chem. Soc., 1971, 93, 7275-7282.
17. 12. Maverick, E.; Trueblood, K.N.; Bekoe, D.A., Acta Cryst., 1978, B34, 2777-2781.
18. 13. Jeffrey, G.A.; Ruble, J.R.; McMullan, R.K.; Pople, J.A., Proc. Roy. Soc. Ser. A, 1987, 414, 47-57.
19. 14. Komatsu, K.; Jinbu, Y.; Gillette, G.R.; West, W., Chem. Lett., 1988, 2029-2032.
20. 15. Frank, N.L.; Baldridge, K.K.; Gantzel, P.; Siegel, J.S., Tetrahedron Lett., 1995, 36, 4389 -4392.
21. 16. Cossu, S.; de Lucchi, O.; Lucchini, V.; Valle, G.; Balci, M.; Dastan, A.; Demirci, B., Tetrahedron Lett., 1997, 38, 5319-5322.
22. 17. Cardullo, F.; Giulfrida, D.; Kohnke, F.H.; Raymo, F.M.; Stoddart, J.F.; Williams, D.J., Angew. Chem., Int. Edn. Engl., 1996, 35, 339-341.
23. 18. Burgi, H.-B.; Baldridge, K.K.; Hardcastle, K.; Frank, N.L.; Gantzel, P.; Siegel, J.S.; Ziller, J., Angew. Chem., Int. Edn. Engl., 1995, 34, 1454-1456.
24. 19. Diercks, R.; Volhardt, K.P.C., J. Am. Chem. Soc., 1986, 108, 3150-3152.
25. 20. Cobbledick, R.E.; Einstein, F.W.B., Acta Cryst., 1976, B32, 1908-1909; Thummel, R.P.; Korp, J.D.; Bernal, I.; Harlow, R.L.; Soulen, R.L., J. Am. Chem. Soc., 1976, 99, 6916 -6918.
26. 20. Cobbledick, R.E.; Einstein, F.W.B., Acta Cryst., 1976, B32, 1908-1909; Thummel, R.P.; Korp, J.D.; Bernal, I.; Harlow, R.L.; Soulen, R.L., J. Am. Chem. Soc., 1976, 99, 6916 -6918.
27. 21. Kohnke, F.; Mathias, J.P.; Stoddard, J.F.; Slawin, A.M.Z.; Williams, D.J., Acta Cryst., 1992, C48, 663-665.
28. 22. Diercks, R.; Volhardt, K.P.C., Angew. Chem., Int. Edn. Engl., 1986, 25, 266-268.
29. 23. Winter, W.; Butters, T., Acta Cryst., 1981, B37, 1524-1527.
30. 24. Yokozeki, A.; Wilcox Jr., C.F.; Bauer, S.H., J. Am. Chem. Soc., 1974, 96, 1026-1032.
31. 25. Berris, B.C.; Hovakeemian, G.H.; Lai, Y.H.; Mestdagh, H.; Volhardt, K.P.C., J. Am. Chem. Soc., 1985, 107, 5670-5687.
32. 26. Schulman, J.M.; Disch, R.L.,J. Am. Chem. Soc., 1996, 118, 8470-8474; Maksic, Z.B.; Kovacek, D.; Eckert-Maksic, M.; Bockmann, M.; Klessinger, M., J. Chem. Phys. ,1995, 99, 6410-6416.
33. 26. Schulman, J.M.; Disch, R.L.,J. Am. Chem. Soc., 1996, 118, 8470-8474; Maksic, Z.B.; Kovacek, D.; Eckert-Maksic, M.; Bockmann, M.; Klessinger, M., J. Chem. Phys. ,1995, 99, 6410-6416.
34. 27. Krygowski, T.M.; Ciesielski, A.; Bird, C.W.; Kotschy, A., J. Chem. Inf. Comput. Sci., 1995, 35, 203-210.