Theoretical study of the structure and tautomerism of N1-unsubstituted pyrazoles in the solid state

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 1, 1997, Pages 101-109

  De Paz, José Luis G ^a   Elguero, José ^b   Foces Foces, Concepción ^c   Llamas Saiz, Antonio L ^c   Aguilar Parrilla, Francisco ^d   Klein, Olivier ^d   Limbach, Hans Heinrich ^d  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000244276     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a603035a     Document Type: Article

References (51)

1. A. Baldy, J. Elguero, R. Faure, M. Pierrot and E. J. Vincent, J. Am. Chem. Soc., 1985, 107, 5290.
2. J. A. S. Smith, B. Wehrle, F. Aguilar-Parrilla, H.-H. Limbach, C. Foces-Foces, F. H. Cano, J. Elguero, A. Baldy, M. Pierrot, M. M. T. Khursid and J. B. Larcombe-McDouall, J. Am. Chem. Soc., 1989, 111, 7304.
3. F. Aguilar-Parrilla, G. Scherer, H.-H. Limbach, C. Foces-Foces, F. H. Cano, J. A. S. Smith, C. Toiron and J. Elguero, J. Am. Chem. Soc., 1992, 114, 9657.
4. F. Aguilar-Parrilla, C. Cativiela, M. D. Díaz de Villegas, J. Elguero, C. Foces-Foces, J. I. García, F. H. Cano, H.-H. Limbach, J. A. S. Smith and C. Toiron, J. Chem. Soc., Perkin Trans. 2, 1992, 1737.
5. J. Elguero, F. H. Cano, C. Foces-Foces, A. L. Llamas-Saiz, H.-H. Limbach, F. Aguilar-Parrilla, R. M. Claramunt and C. López, J. Heterocycl. Chem., 1994, 31, 695.
6. H.-H. Limbach, F. Aguilar-Parrilla, O. Klein, J. Elguero and N. Jagerovic, unpublished results.
7. J. Elguero, C. Marzin, A. R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Academic Press, New York, 1976.
8. F. Aguilar-Parrilla, H.-H. Limbach, C. Foces-Foces, F. H. Cano, J. Elguero and N. Jagerovic, J. Org. Chem., 1995, 60, 1965.
9. A. L. Llamas-Saiz, C. Foces-Foces, F. H. Cano, P. Jiménez, J. Laynez, W. Meutermans, J. Elguero, H.-H. Limbach and F. Aguilar-Parrilla, Acta Crystallogr., Sect. B, 1994, 50, 746.
10. C. Foces-Foces, A. L. Llamas-Saiz, R. M. Claramunt, C. López and J. Elguero, J. Chem. Soc., Chem. Commun., 1994, 1143.
11. B. Beagley, K. J. Farnworth, E. T. Moss, R. G. Pritchard, S. Tajammal and A. E. Tipping, Acta Crystallogr., Sect. C, 1994, 50, 1130.
12. A. L. Llamas-Saiz, C. Foces-Foces, I. Sobrados, J. Elguero and W. Meutermans, Acta Crystallogr., Sect. C, 1993, 49, 724.
13. J. Elguero, N. Jagerovic, C. Foces-Foces, F. H. Cano, M. V. Roux, F. Aguilar-Parrilla and H.-H. Limbach, J. Heterocycl. Chem., 1995, 32, 451.
14. J. Berthou, J. Elguero and C. Rérat, Acta Crystallogr., Sect. B, 1970, 26, 1880.
15. T. La Cour and S. E. Rasmussen, Acta Chem. Scand., 1973, 27, 1845.
16. C. Fontenas, C. Foces-Foces and J. Elguero, unpublished results.
17. C. Foces-Foces, F. H. Cano and J. Elguero, Gazz. Chim. Ital., 1993, 123, 477.
18. P. Domiano and A. Musati, Cryst. Struct. Commun., 1974, 4, 713.
19. H.-H. Limbach, Dynamic NMR Spectroscopy in the Presence of Kinetic H/D Isotope Effects, in NMR Basic Principles and Progress, Springer, Berlin, 1991.
20. H.-H. Limbach, G. Scherer, L. Meschede, F. Aguilar-Parrilla, B. Wehrle, J. Braun, Ch. Hoelger, H. Benedict, G. Buthowsky, W. P. Fehlhammer, J. Elguero, J. A. S. Smith and B. Chaudret, in Ultrafast Reaction Dynamics and Solvent Effects, eds. Y. Gauduel and P. J. Rossky, Am. Inst. Phys., New York, 1994, A.P. Conf. Proc. 258, pp. 225-239.
21. Modern Techniques in Computational Chemistry: MOTECC-89, ed. E. Clementi, ESCOM Science Publishers, Leiden, 1989.
22. Modern Techniques in Computational Chemistry: MOTECC-90, ed. E. Clementi, ESCOM Science Publishers, Leiden, 1990.
23. KGNMOL: R. Romperts and E. Clementi, IBM Technical Report KGN-118, 119, 1988; QCPE 1988, 8 , 33, program 538; E. Clementi and G. Corongiu, in ch. 6 of ref. 21; E. Clementi, G. Corongiu and S. Chakravorty, in ch. 7 of ref. 22. KGNMOL is included in MOTECC code.
24. HONDO: M. Dupuis, J. Rys and H. F. King, J. Chem. Phys., 1976, 65, 111; HONDO7: M. Dupuis, J. D. Watts, G. J. B. Hurst and H. O. Villar, QCPE, 1987, program 544; HONDO8: M. Dupuis, P. Mourgenot, J. D. Watts, G. J. B. Hurst and H. O. Villar, in ch. 7 of ref. 22; A. Dupuis, A. Farazdel, S. P. Karna and S. A. Maluendes, in ch. 6 of ref. 23. HONDO8 is included in MOTECC code.
25. GAUSSIAN86, C. M. J. Frisch, J. S. Binkley, H. B. Schelegel, K. Raghavachari, C. F. Melius, P. L. Martin, J. J. P. Stewart, F. W. Bobrowitz, C. M. Rohlfing, L. R. Kahn, D. J. Defrees, R. Seeger, R. A. Whiteside, D. J. Fox, E. M. Fluder and J. A. Pople, Gaussian Inc., Pittsburg, PA, 1984.
26. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
27. P. Van Duijneveldt, IBM Technical Report RJ-945, 1971. Contraction of the basis are described in L. Gianolio, R. Pavani and E. Clementi, Gazz. Chim. Ital., 1978, 108, 181 and in L. Gianolio and E. Clementi, Gazz. Chim. Ital., 1980, 110, 179.
28. P. Van Duijneveldt, IBM Technical Report RJ-945, 1971. Contraction of the basis are described in L. Gianolio, R. Pavani and E. Clementi, Gazz. Chim. Ital., 1978, 108, 181 and in L. Gianolio and E. Clementi, Gazz. Chim. Ital., 1980, 110, 179.
29. P. Van Duijneveldt, IBM Technical Report RJ-945, 1971. Contraction of the basis are described in L. Gianolio, R. Pavani and E. Clementi, Gazz. Chim. Ital., 1978, 108, 181 and in L. Gianolio and E. Clementi, Gazz. Chim. Ital., 1980, 110, 179.
30. C. Urdaneta, G. Corongiu and E. Clementi, IBM Technical Report KGN-133 (1987); E. Clementi and G. Corongiu, Chem. Phys. Lett., 1982, 90, 359 and IBM Technical Report POK-11 (1982).
31. C. Urdaneta, G. Corongiu and E. Clementi, IBM Technical Report KGN-133 (1987); E. Clementi and G. Corongiu, Chem. Phys. Lett., 1982, 90, 359 and IBM Technical Report POK-11 (1982).
32. T. H. Dunning and P. J. Hay, in Methods of Electronic Theory Structure, ed. H. E. Schaeffer III, Plenum Press, New York, 1977.
33. S. F. Boys and F. Bernardi, Mol. Phys., 1970, 19, 553.
34. J. A. Sordo, T. L. Sordo, G. M. Fernández, R. Gomperts, S. Chin and E. Clementi, J. Chem. Phys., 1989, 90, 6361.
35. O. Mo, J. L. G. de Paz and M. Yáñez, Theor. Chim. Acta, 1988, 73, 307.
36. O. Mó, J. L. G. de Paz and M. Yáñez, J. Phys. Chem., 1986, 90, 5597.
37. D. Spangler, I. H. Williams and G. M. Maggiora, J. Comput. Chem., 1983, 4, 524.
38. B. A. Murtagh and R. W. H. Sargent, Comput. J., 1970, 13, 185; H. B. Schlegel, J. Comput. Chem., 1984, 5, 612.
39. B. A. Murtagh and R. W. H. Sargent, Comput. J., 1970, 13, 185; H. B. Schlegel, J. Comput. Chem., 1984, 5, 612.
40. C. Moller and M. S. Plesset, Phys. Rev., 1934, 46, 618. For implementation in KGNMOL see ref. 23; in HONDO see ref. 24, and in GAUSSIAN see ref. 26.
41. J. P. Perdew, Phys. Rev. B, 1986, 33, 8822; J. Perdew and A. Zunger, Phys. Rev. B, 1981, 23, 5048. For implementation in KGNMOL, see ref. 24.
42. J. P. Perdew, Phys. Rev. B, 1986, 33, 8822; J. Perdew and A. Zunger, Phys. Rev. B, 1981, 23, 5048. For implementation in KGNMOL, see ref. 24.
43. J. L. Brédas, M. P. Poskin, J. Delhalle, J. M. André and H. Chojnaki, J. Phys. Chem., 1984, 88, 5882.
44. P. Ahlberg, K. Janné, S. Löfás, F. Nettelblad and L. Swahn, J. Phys. Org. Chem., 1989, 2, 429; P. Svensson, N. Å. Bergmann and P. Ahlberg, J. Chem. Soc., Chem. Commun., 1990, 82; Z. Naturforsch., Teil A, 1989, 44, 473; K. A. Nguyen, M. S. Gordon and D. G. Truhlar, J. Am. Chem. Soc., 1991, 113, 1596.
45. P. Ahlberg, K. Janné, S. Löfás, F. Nettelblad and L. Swahn, J. Phys. Org. Chem., 1989, 2, 429; P. Svensson, N. Å. Bergmann and P. Ahlberg, J. Chem. Soc., Chem. Commun., 1990, 82; Z. Naturforsch., Teil A, 1989, 44, 473; K. A. Nguyen, M. S. Gordon and D. G. Truhlar, J. Am. Chem. Soc., 1991, 113, 1596.
46. P. Ahlberg, K. Janné, S. Löfás, F. Nettelblad and L. Swahn, J. Phys. Org. Chem., 1989, 2, 429; P. Svensson, N. Å. Bergmann and P. Ahlberg, J. Chem. Soc., Chem. Commun., 1990, 82; Z. Naturforsch., Teil A, 1989, 44, 473; K. A. Nguyen, M. S. Gordon and D. G. Truhlar, J. Am. Chem. Soc., 1991, 113, 1596.
47. P. Ahlberg, K. Janné, S. Löfás, F. Nettelblad and L. Swahn, J. Phys. Org. Chem., 1989, 2, 429; P. Svensson, N. Å. Bergmann and P. Ahlberg, J. Chem. Soc., Chem. Commun., 1990, 82; Z. Naturforsch., Teil A, 1989, 44, 473; K. A. Nguyen, M. S. Gordon and D. G. Truhlar, J. Am. Chem. Soc., 1991, 113, 1596.
48. Y. Kim, J. Am. Chem. Soc., 1996, 118, 1522.
49. L. Jaroszewski, B. Lesyng, J. J. Tanner and J. A. McCammon, Chem. Phys. Lett., 1990, 175, 282.
50. L. Meschede and H.-H. Limbach, J. Phys. Chem., 1991, 95, 10267.
51. M. Perrin, A. Thozet, P. Cabildo, R. M. Claramunt, E. Valentin and J. Elguero, Can. J. Chem., 1993, 71, 1443.