Separation of the energetic and geometric contribution to the aromaticity. Part IX. Aromaticity of pyrazoles in dependence on the kind of substitution

Tetrahedron

Volumn 54, Issue 40, 1998, Pages 12295-12300

  Krygowski, Tadeusz M ^a   Anulewicz, Romana ^a   Cyrański, Michał K ^a   Puchała, Agnieszka ^b   Rasała, Danuta ^b  

^a UNIVERSITY OF WARSAW   (Poland)

^b JAN KOCHANOWSKI UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ENERGY TRANSFER; GEOMETRY; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 0032192432     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00749-2     Document Type: Article

References (30)

1. 1 Krygowski, T.M. and Cyrański, M.K., Tetrahedron, 1996, 52, 10-255
2. 2. Bird, C.W., Tetrahedron, 1985, 41, 1409, Tetrahedron, 1992, 48, 335.
3. 2. Bird, C.W., Tetrahedron, 1985, 41, 1409, Tetrahedron, 1992, 48, 335.
4. 3. Katritzky, A.R., Barczyński, P., Musumurra, G., Pisano, D. and Szafran, M., J. Am. Chem. Soc., 1989, 111, 7.; Katritzky, A.R., Feygelman, V., Musumurra, G, Barczyński, P. and Szafran, M., J. Prakt. Chem. 1990, 332, 853; Katritzky, A.R., Feygelman, V., Musumurra, G., Barczyński, P and Szafran, M, J. Prakt. Chem. 1990, 332, 870; Katritzky, A.R., Barczyński, P., J.Prakt. Chem., 1990, 332, 885. Katritzky, A.R., Karelson, M., Sild S., Krygowski, T.M. and Jug, K., J. Org. Chem., submitted.
5. 3. Katritzky, A.R., Barczyński, P., Musumurra, G., Pisano, D. and Szafran, M., J. Am. Chem. Soc., 1989, 111, 7.; Katritzky, A.R., Feygelman, V., Musumurra, G, Barczyński, P. and Szafran, M., J. Prakt. Chem. 1990, 332, 853; Katritzky, A.R., Feygelman, V., Musumurra, G., Barczyński, P and Szafran, M, J. Prakt. Chem. 1990, 332, 870; Katritzky, A.R., Barczyński, P., J.Prakt. Chem., 1990, 332, 885. Katritzky, A.R., Karelson, M., Sild S., Krygowski, T.M. and Jug, K., J. Org. Chem., submitted.
6. 3. Katritzky, A.R., Barczyński, P., Musumurra, G., Pisano, D. and Szafran, M., J. Am. Chem. Soc., 1989, 111, 7.; Katritzky, A.R., Feygelman, V., Musumurra, G, Barczyński, P. and Szafran, M., J. Prakt. Chem. 1990, 332, 853; Katritzky, A.R., Feygelman, V., Musumurra, G., Barczyński, P and Szafran, M, J. Prakt. Chem. 1990, 332, 870; Katritzky, A.R., Barczyński, P., J.Prakt. Chem., 1990, 332, 885. Katritzky, A.R., Karelson, M., Sild S., Krygowski, T.M. and Jug, K., J. Org. Chem., submitted.
7. 3. Katritzky, A.R., Barczyński, P., Musumurra, G., Pisano, D. and Szafran, M., J. Am. Chem. Soc., 1989, 111, 7.; Katritzky, A.R., Feygelman, V., Musumurra, G, Barczyński, P. and Szafran, M., J. Prakt. Chem. 1990, 332, 853; Katritzky, A.R., Feygelman, V., Musumurra, G., Barczyński, P and Szafran, M, J. Prakt. Chem. 1990, 332, 870; Katritzky, A.R., Barczyński, P., J.Prakt. Chem., 1990, 332, 885. Katritzky, A.R., Karelson, M., Sild S., Krygowski, T.M. and Jug, K., J. Org. Chem., submitted.
8. 3. Katritzky, A.R., Barczyński, P., Musumurra, G., Pisano, D. and Szafran, M., J. Am. Chem. Soc., 1989, 111, 7.; Katritzky, A.R., Feygelman, V., Musumurra, G, Barczyński, P. and Szafran, M., J. Prakt. Chem. 1990, 332, 853; Katritzky, A.R., Feygelman, V., Musumurra, G., Barczyński, P and Szafran, M, J. Prakt. Chem. 1990, 332, 870; Katritzky, A.R., Barczyński, P., J.Prakt. Chem., 1990, 332, 885. Katritzky, A.R., Karelson, M., Sild S., Krygowski, T.M. and Jug, K., J. Org. Chem., submitted.
9. 4 Jug, K. and Koester, A., J. Phys. Org. Chem., 1991, 4, 163.
10. 5 Cyrański, M.K., and Krygowski, T.M., Tetrahedron, 1996, 52, 13795
11. 6. Katritzky, R. A., Karelson, M. and Well, A.P., J.Org. Chem., 1996, 61, 1619
12. 7. Cyrański, M.K., Krygowski, T.M., Wisiorowski, M., van Eikema Hommes N.J.R. and Schleyer, P.v. R., Angew. Chem. 1998, 110, 197; Angew. Chem. Int. Ed. 1998, 37, 177.
13. 7. Cyrański, M.K., Krygowski, T.M., Wisiorowski, M., van Eikema Hommes N.J.R. and Schleyer, P.v. R., Angew. Chem. 1998, 110, 197; Angew. Chem. Int. Ed. 1998, 37, 177.
14. 8. Kruszewski, J. and Krygowski, T.M., Tetr. Letters, 1972, 3839, Krygowski, T.M., J. Chem. Inf. Comput. Sci., 1993, 33, 70.
15. 8. Kruszewski, J. and Krygowski, T.M., Tetr. Letters, 1972, 3839, Krygowski, T.M., J. Chem. Inf. Comput. Sci., 1993, 33, 70.
16. 9 Schleyer, P. v. R., Maerker, C., Dransfeld, A, Jiao, H., van Eikema Hommes, N. J. R., J. Am. Chem. Soc. 1996, 118, 6317
17. 10. Triclinic, space group P-I, a=9.181 (2) A, b=12.420 (2) A, c=21.357 (4) A, α=87.56 (3) deg., β=83.70 (3) deg., γ=87.65 (3) deg., Z=4; 9142 independent reflections, R=0.0505. Further details of the crystal structure: list of structure factors, anisotropic displacement parameters, H-atom coordinates, complete geometry will be sent to the Cambridge Structural Database
18. 11. Triclinic, space group P-I, a=8.597 (2), b=10.508 (2) A, c=12.472 (2), α=105.38 (3) deg., β=98.95 (3) deg, γ=101.29 (3) deg., Z=2, 4360 independent reflections, R=0.0538. Further details of the crystal structure: list of structure factors, anisotropic displacement parameters, H-atom coordinates, complete geometry will be sent to the Cambridge Structural Database.
19. 12. Puchala, A., Rasala, D., Kolehmainen, E and Prokesova, M., Org.Prep.Proc.Int., 1997, 29, 212
20. 13. Sheldrick G.M., Acta Crystallogr. 1990, A46, 467.
21. 14. Sheldrick G.M., SHELXL93. Program for Refinement of Crystal Structure. Univ. of Gottingen, Germany 1993
22. 15. International Tables for X-Ray Crystallography, vol. IV., Kynoch Press, Birmingham 1974.
23. 16. 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 ; Bmldey, J. S.; Defrees, D. J., Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C. and J. A. Pople. Gaussian, Inc., Pittsburgh PA, 1995
24. 17. Krygowski, T.M. and Cyrański, M., Tetrahedron, 1996, 52, 1713.
25. 18. Cyrański, M.K., Krygowski, T.M. and Bird, C.W., Tetrahedron, 1998, 54, 000.
26. 19. Allen, F.H., Davies, J.E., Galloy, J.J., Johnson O., Kennard, O., McRae Mitchell, E.M., Mitchell, G.F., Smith, J.M. and Watson D.G.J., J.Chem.Inf.Comput.Sci. 1991 31, 187; Allen, F.H., Bellard, S., Brice, M.D., Cartwright, B. A., Doubleday, A., Higgs, H., Hummelink, T Hummelink-Peters, B.G., Kennard, O., Motherwell, W.D.S., Rodgers, J.R, Watson DG., Acta Cryst. 1979, B35, 2331.
27. 19. Allen, F.H., Davies, J.E., Galloy, J.J., Johnson O., Kennard, O., McRae Mitchell, E.M., Mitchell, G.F., Smith, J.M. and Watson D.G.J., J.Chem.Inf.Comput.Sci. 1991 31, 187; Allen, F.H., Bellard, S., Brice, M.D., Cartwright, B. A., Doubleday, A., Higgs, H., Hummelink, T Hummelink-Peters, B.G., Kennard, O., Motherwell, W.D.S., Rodgers, J.R, Watson DG., Acta Cryst. 1979, B35, 2331.
28. 20. Krygowski, T.M., Cyrański, M.K., Nakata, K., Fujio, M. and Tsuno, Y., Tetrahedron, 1997, 53, 11383; and Krygowski, T.M., Cyranski, M.K., Nakata, K., Fujio, M. and Tsuno, Y., Tetrahedron, 1998, 54, 3303. cf. Gobbi A. and Frenking, G., J. Am. Chem. Soc., 1994, 116, 9275.
29. 20. Krygowski, T.M., Cyrański, M.K., Nakata, K., Fujio, M. and Tsuno, Y., Tetrahedron, 1997, 53, 11383; and Krygowski, T.M., Cyranski, M.K., Nakata, K., Fujio, M. and Tsuno, Y., Tetrahedron, 1998, 54, 3303. cf. Gobbi A. and Frenking, G., J. Am. Chem. Soc., 1994, 116, 9275.
30. 20. Krygowski, T.M., Cyrański, M.K., Nakata, K., Fujio, M. and Tsuno, Y., Tetrahedron, 1997, 53, 11383; and Krygowski, T.M., Cyranski, M.K., Nakata, K., Fujio, M. and Tsuno, Y., Tetrahedron, 1998, 54, 3303. cf. Gobbi A. and Frenking, G., J. Am. Chem. Soc., 1994, 116, 9275.