The imbalanced Kekule structure contributions in the ring in 1,3,5-trisubstituted benzene derivatives: Low temperature X-ray study on 1,3,5-trimethoxybenzene, and ab initio calculations on 1,3,5-triformylobenzene and trimethoxybenzene and the related di-substituted systems

Tetrahedron

Volumn 52, Issue 34, 1996, Pages 11379-11384

  Howard, Sean T ^a   Krygowski, Tadeusz Marek ^b   Glówka, Marek L ^c  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF WARSAW   (Poland)

^c LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; THEORY; X RAY ANALYSIS;

EID: 0030593655     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00664-3     Document Type: Article

References (30)

1. 1. Jeffrey, G.A.; Ruble, J.R.; McMullen, R.K., Pople, J.A. Proc. Roy. Soc. Ser. A. 1987, 414, 47.
2. 2. Hiberty, Ph.C.; Shaik, S.S.; Lefour, J.-M.; Ohanessian, G. J. Org.. Chem. Soc. 1985, 50, 4657.
3. 3. Shaik, S.S.; Hiberty, Ph. C.; Lefour, J.-M., Ohanessian, G. J. Am. Chem. Soc., 1987, 109, 363.
4. 4. Hiberty, Ph., C. Topics in Current Chemistry, 1990, 153, 27.
5. 5. Jug, K; Koester, A. J. Am. Chem. Soc., 1990, 112, 6772.
6. 6. Glendening, E.D.; Faust, R.; Streitwieser, A.; Vollhardt, K. P. C.; Weinhold, F. J. Am. Chem. Soc. 1993, 115, 10952.
7. 7. Krygowski, T. M.; Ciesielski, A.; Świrska B.; Leszczyński P., Pol. J. Chem., 1994, 68, 2097.
8. 8. Krygowski, T.M.; Cyrański M. Tetrahedron, 1996, 52, 1713.
9. 9. Stanger, A.; Vollhardt, K.P.C., J. Org. Chem. 1988, 53, 4889.
10. 10. Minkin V. I., Glukhovtsev, M. N., Simkin B. Ya., Aromaticity and Antiaromaticity - Electronic and Structural Aspects, J Wiley, 1994, New York.
11. 11. Krygowski ,T.M.; Anulewicz, R.; Jarmula, A.; Bak, T.; Rasala, D.; Howard, S. T. Tetrahedron, 1994, 50, 13155.
12. 12. Krygowski, T.M.; Anulewicz, R.; Kruszewski, J. Acta Cryst. 1983, B39, 372.
13. 13. Stults, B. R. Cryst. Struct. Com., 1979, 8, 401.
14. 14. Maulitz, A. H., Stellberg, P. and Boese, R., J. Mol. Struct. (Theochem) 1995, 338-131.
15. 15. Główka, M.; Iwanicka, I. Acta Cryst. 1991, C47, 1036.
16. 16. SHELDRICK, G.M.,(1993) SHELX93. Program for the Refinement of Crystal Structures. Univ. of Goettingen, Germany.
17. 17. Główka, M.; Krygowski, T.M.; Anulewicz, R. in preparation
18. 18. Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon, M.S.; Jensen, J.H.; Koseki, S,; Matsunaga, N.; Nguyen, K.A.; Su, S.J.; Windus, T.L., Dupuis, M.; Montgomery, J.A. J. Comput. Chem. 1993, 14, 1347.
19. 19. Binkley, J.S.; Pople, J.A.; Hehre, W.J. J. Am. Chem. Soc. 1980, 120, 939.
20. 20. Krishnan, R.; Binkley, I.S.; Seeger, R.; Pople, J.A. J. Chem. Phys. 1980, 72, 650.
21. 21. Exner, O.; in Advances in Free Energy Relationships, Chapman, N.B. and Shorter, J., Edts, Plenum Press, Londnon, 1972 pp. 28,29.
22. 22. Krygowski, T.M., Howard, S.T., Martynowski, D., and Główka M.L., J. Phys. Org. Chem., submitted.
23. 23. Krygowski, T.M., Anulewicz, R. and Hiberty Ph. C., J. Org. Chem submitted.
24. 24. Jackman, L.M.; Elvidge, J.A., J. Chem. Soc. 1961, 859; Sondheimer, F., Pure Appl. Chem. 1964, 859.
25. 24. Jackman, L.M.; Elvidge, J.A., J. Chem. Soc. 1961, 859; Sondheimer, F., Pure Appl. Chem. 1964, 859.
26. 25. cf aromaticity indices based on the alternation of bond lengths: Julg, A. ; Francois, Ph., Theor. Chim. Acta, 1967, 7, 249; Kruszewski, J.; Krygowski, T.M. Tetr. Letters, 1972, 3839; Bird, C.W., Tetrahedron 1985, 41, 1414. For review cf. Krygowskj T.M., J. Chem. Inf. Comput. Sci., 1993, 33, 70.
27. 25. cf aromaticity indices based on the alternation of bond lengths: Julg, A. ; Francois, Ph., Theor. Chim. Acta, 1967, 7, 249; Kruszewski, J.; Krygowski, T.M. Tetr. Letters, 1972, 3839; Bird, C.W., Tetrahedron 1985, 41, 1414. For review cf. Krygowskj T.M., J. Chem. Inf. Comput. Sci., 1993, 33, 70.
28. 25. cf aromaticity indices based on the alternation of bond lengths: Julg, A. ; Francois, Ph., Theor. Chim. Acta, 1967, 7, 249; Kruszewski, J.; Krygowski, T.M. Tetr. Letters, 1972, 3839; Bird, C.W., Tetrahedron 1985, 41, 1414. For review cf. Krygowskj T.M., J. Chem. Inf. Comput. Sci., 1993, 33, 70.
29. 25. cf aromaticity indices based on the alternation of bond lengths: Julg, A. ; Francois, Ph., Theor. Chim. Acta, 1967, 7, 249; Kruszewski, J.; Krygowski, T.M. Tetr. Letters, 1972, 3839; Bird, C.W., Tetrahedron 1985, 41, 1414. For review cf. Krygowskj T.M., J. Chem. Inf. Comput. Sci., 1993, 33, 70.
30. 26. Cyvin, S. J.; Molecular Vibrations and Mean Square Amplitude, Elsevier Publishing Company, 1968, chpt. XI and XII.