Tautomerism of 1-(2′,4′-dinitrophenyl)-3-methyl-2-pyrazolin-5-one: Theoretical calculations, solid and solution NMR studies and X-ray crystallography

New Journal of Chemistry

Volumn 22, Issue 12, 1998, Pages 1421-1430

  Dardonville, Christophe ^a   Elguero, José ^a   Rozas, Isabel ^a   Fernández Castaño, Cristina ^b   Foces Foces, Concepción ^b   Sobrados, Isabel ^c  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^c INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000385122     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805415k     Document Type: Article

References (51)

1. (a) J. Elguero, C. Marzin, A. R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, 1976.
2. (b) J. S. Kwiatkowsky and B. Pullman, Adv. Heterocycl. Chem., 1975, 18, 199.
3. (c) J. Elguero and A. R. Katritzky, The Tautomerism of Heterocycles, Academic Press, New York, 1999, in press.
4. (a) R. W. Taft, F. Anvia, M. Taagepera, J. Catalan and J. Elguero, J. Am. Chem. Soc., 1986, 108, 3237.
5. (b) J. Catalan, M. Sánchez-Cabezudo, J. L. G. de Paz, J. Elguero, R. W. Taft and F. Anvia, J. Comput. Chem., 1989, 10, 426.
6. (c) W. Freyer, H. Koppel, R. Radeglia and G. Malewski, J. Prakt. Chem., 1983, 325, 238.
7. (a) J. Elguero, in Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1984, vol. 5, p. 167.
8. (b) J. Elguero, Comprehensive Heterocyclic Chemistry, ibid., 1996, vol. 3, p. 1.
9. J.-L. Abboud, M. J. Kamlet and R. W. Taft, Prog. Phys. Org. Chem., 1981, 13, 485.
10. (a) F. Bechtel, J. Gaultier and C. H. Hauw, Cryst. Struct. Commun., 1973, 3, 469.
11. (b) C. Foces-Foces, C. Fontenas, J. Elguero and I. Sobrados, An. Quim. Int. Ed., 1997, 93, 219.
12. (c) J. Sieler, R. Kempe, L. Henning and J. Becher, Z. Kristallogr., 1992, 198, 313.
13. (a) J. Elguero, G. Guiraud, R. Jacquier and G. Tarrago, Bull. Soc. Chim., 1966, 775.
14. (b) J. Elguero, G. Guiraud, R. Jacquier and H. C. N. Tien Duc, Bull. Soc. Chim., 1967, 328.
15. (c) J. Elguero, G. Guiraud, R. Jacquier and G. Tarrago, Bull. Soc. Chim., 1968, 5019.
16. O. G. Parchment, D. V. S. Green, P. J. Taylor and I. H. Hillier, J. Am. Chem. Soc., 1993, 115, 2352.
17. M. Cao, B. J. Teppen, D. M. Miller, J. Pranata and L. Schäfer, J. Phys. Chem., 1994, 98, 11353.
18. F. J. Luque, J. M. López-Bes, J. Cemeli, M. Aroztegui and M. Orozco, Theor. Chem. Acc., 1997, 96, 105.
19. S. Ono, K. Okazaki, M. Sakurai and Y. Inoue, J. Phys. Chem. A, 1997, 101, 3769.
20. G. Tschmutova and H. Ahlbrecht, Z. Naturforsch. B, 1997, 52, 535.
21. (a) AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
22. (b) PM3: J. J. P. Stewart, J. Comput. Chem., 1991, 12, 320.
23. (c) AiOPXC Version 6.0, QCPE No. 455, Department of Chemistry, Indiana University, Bloomington, Indiana, 1991.
24. 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. Ortíz, J. B. Foresman, 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. J. P. Stewart, M. Head-Gordon, C. González and J. A. Pople, Gaussian 94, Gaussian, Inc., Pittsburgh, PA, 1995.
25. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
26. (b) C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1993, 37, 785.
27. SIR92: A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., 1994, 27, 435.
28. International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, UK, 1974.
29. S. R. Hall, H. D. Flack and J. M. Stewart, Xtal3.2, Univ. Western Australia, Lamb, Perth, 1994.
30. J. M. Martinez-Ripoll and F. H. Cano, PESOS, unpublished program.
31. M. Nardelli, Comput. Chem., 1983, 7, 95.
32. J. J. P. Stewart, MOPAC Manual, 6th Edn, 1990.
33. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1.
34. G. Klebe, The Application of Charge Density Research to Chemistry and Drug Design, Plenum Press, New York, 1991, p. 287.
35. F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, C. F. Macrae, E. M. Mitchell, J. F. Mitchell J. M. Smith and D. G. Watson, J. Chem. Info. Comput. Sci., 1991, 31, 187.
36. M. Kimura, I. Okabayashi and N. Yasuoka, Chem. Pharm. Bull., 1984, 32, 318.
37. J. Becher, M. Begtrup, A. Gjerlov, S. Larsen, W. Dehaen and L. K. Christensen, Acta Chem. Scand., 1995, 49, 57.
38. F. Bechtel, J. Gaultier and C. H. Hauw, Cryst. Struct. Commun., 1973, 3, 473.
39. A. Domenicano and P. Murray-Rust, Tetrahedron Lett., 1979, 24, 2283.
40. C. Fernández-Castaño, C. Foces-Foces, F. H. Cano, R. M. Claramunt, C. Escolãstico, A. Fruchier and J. Elguero, New J. Chem., 1997, 21, 195.
41. T. M. Krygowsky, Prog. Phys. Org. Chem., 1990, 17, 239.
42. F. R. Fronczek, F. J. Parodi, N. H. Fischer, T. C.-Y. Hsieh and B.-Y. Chang, Acta Crystallogr., Sect. C, 1989, 45, 2027.
43. J.-L. Galigné and J. Falgueirettes, Acta Crystallogr. Sect. B, 1969, 25, 1637.
44. J.-L. Galigné and J. Falgueirettes, Acta Crystallogr. Sect. B, 1970, 26, 380.
45. S. M. Naidu, M. Krishnaiah, K. Sivakumar and R. P. Sharma, Acta Crystallogr. Sect. C, 1996, 52, 1056.
46. B. K. Vainshtein, V. M. Fridkin and V. L. Indenbom, Modern Crystallography II, Springer-Verlag, Berlin, 1982, p. 87.
47. I. André, C. Foces-Foces, F. H. Cano, and M. Martínez-Ripoll, Acta Crystallogr. Sect. B, 1997, 53, 996.
48. R. Taylor, A. Mullaley and G. W. Mullier, Pestic. Sci., 1990, 29, 197.
49. F. H. Cano and M. Martínez-Ripoll, J. Mol. Struct. (TEOCHEM), 1992, 258, 139.
50. C. Foces-Foces, C. Fontenas, J. Elguero and I. Sobrados, An. Quím. Int. Ed., 1997, 93, 219 and references therein.
51. G. R. Desiraju, Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989, pp. 147-157.