Abstract
The structures of 1,4-bis(pyrazol-1'-yl)-2,3,5,6- tetrakis(3'',5''-dimethylpyrazol-1''-yl) benzene 1, its monohydrate, 1a, four 1 : 2 host : guest complexes, 1b–1e (acetic, propionic, pentanoic, and (±)-2-methyl butyric acids) and a di-picrate salt, 1f, have been determined by X-Ray analysis. In all complexes, in the salt and in the monohydrate compound, the host molecules are hydrogen bonded to two centrosymmetric related guests and to the water molecule which is disordered over two positions to mimic the inclusion complexes. In all compounds, the host exhibits Ci symmetry having the lone pair on the N(2) atom of each pyrazole pointing alternately upwards (u) and downwards (d) from the benzene ring. 1H and 13C NMR spectra of the free host 1 and of the complexes are consistent with the ududud conformation and the stoicheiometry of the inclusion compounds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
C. Foces-Foces, A.L. Llamas-Saiz, R.M. Claramunt, N. Jagerovic, M.L. Jimeno and J. Elguero: J. Chem. Soc. Perkin Trans. 2, 1359 (1995).
C. Foces-Foces, A.L. Llamas-Saiz, C. Escolástico, R.M. Claramunt and J. Elguero: J. Phys. Org. Chem. 9, 137 (1996).
C. Foces-Foces, C. Fernández-Castaño, R.M. Claramunt, C. Escolástico and J. Elguero: J. Phys. Org. Chem. 9, 717 (1996).
P. Cornago, C. Escolástico, M.D. Santa María, R.M. Claramunt, C. Fernández-Castaño, C. Foces-Foces, J.-P. Fayet and J. Elguero: Tetrahedron 52, 11057 (1996).
C. Foces-Foces, A.L. Llamas-Saiz, C. Fernández-Castaño, R.M. Claramunt, C. Escolástico, J.L. Lavandera, M.D. Santa María, M.L. Jimeno and J. Elguero: J. Chem. Soc., Perkin Trans. 2, 2173 (1997).
D.D. MacNicol, in J.L. Atwood, J.E.D. Davies and D.D. MacNicol (eds.), Inclusion Compounds, Academic Press, London, v. 2, pp. 123 (1984). D.D. MacNicol and G.A. Downing: Comprehensive Supramolecular Chemistry, Pergamon Press, New York, v. 6, chapter 14, pp. 421 (1996).
F. Vögtle and E. Weber: Angew. Chem., Int. Ed. Engl. 13, 814, (1974). E. Weber: Comprehensive Supramolecular Chemistry, Pergamon Press, New York, v. 6, chapter 17, pp. 535 (1996).
S.A. Bourne, M.R. Caira, L.R. Nassimbeni, M. Sakamoto, K. Tanaka and F. Toda: J. Chem. Soc., Perkin Trans. 2, 899 (1994).
H. Pepermans, M. Gielen, C. Hoogzand and R. Willem: Bull. Soc. Chim. Belg. 92, 465 (1983).
H. Pepermans, R. Willem, M. Gielen and C. Hoogzand: Magn. Reson. Chem. 26, 311 (1988).
M.A. Keegstra, S. De Feyter, F.C. De Schryver and K. Müllen: Angew. Chem. Int. Ed. Engl. 35, 774 (1996).
J.C.J. Bart: Acta Crystallogr., Sect. B. 24, 1277 (1968).
E.M. Larson, R.B. Von Dreele, P. Hanson and J. Devens Gust: Acta Crystallogr., Section C (Cryst. Struct. Commun.) 46, 784 (1990).
R.N. Henrie ?II and W.H. Yeager: Heterocycles 35, 415 (1993).
R. Weiss, B. Pomrehn, F. Hampel and W. Bauer: Angew. Chem. Int. Ed. Engl. 34, 1319 (1995).
H.A.M. Biemans, C. Zhang, P. Smith, H. Kooijman, W.J.J. Smeets, A.L. Spek and E.W. Meijer: J. Org. Chem. 61, 9012 (1996).
C.M. Hartshorn and P.J. Steel: Aust. J. Chem. 48, 1587 (1995); Angew. Chem. Int. Ed. Engl. 35, 2655 (1996).
C. Fernández-Castaño, C. Foces-Foces, F.H. Cano, R.M. Claramunt, C. Escolástico, A. Fruchier, and J. Elguero: New J. Chem. 21, 195 (1997).
J. Cosier and A.M. Glazer: J. Appl. Crystallogr. 19, 105 (1986).
A. Altomare, M.C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori: SIR92, J. Appl. Crystallogr. 27, 435 (1994).
International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, England, Vol. IV (1974).
S.R. Hall and J.M. Stewart: XTAL3.2, Eds. Univs. of Western Australia and Maryland, Perth (1994).
M. Martinez-Ripoll and F.H. Cano: PESOS, Unpublished program.
M. Nardelli: Comput. Chem. 7, 95 (1983).
T.M. Krygowski: in R.W. Taft (ed.), Prog. Phys. Org. Chem., Wiley Interscience, New York, v. 17, pp. 239. (1990).
A. Domenicano and P. Murray-Rust: Tetrahedron Lett. 2283 (1979).
J.J.P. Stewart: MOPAC6.0. Frank J. Seiler Research Laboratory, United States Air Force Academy, CO 80840, USA (1990).
B.K. Vainshtein, V.M. Fridkin and V.L. Indenbom: Modern Crystallography II, Springer-Verlag. Berlin, Heidelberg, New York, pp. 87 (1982).
F.H. Cano and M. Martínez-Ripoll: J. Mol. Struc. (Theochem) 258, 139 (1992).
J.B. Stothers: Carbon-13 NMR Spectroscopy, Academic Press, New York (1972); E. Breitmaier and W. Voelter: 13C NMR Spectroscopy (2nd Edition, Verlag Chemie, Weinheim (1978); H.-O. Kalinowski, S. Berger and S. Braun: Carbon-13 NMR Spectroscopy, John Wiley and Sons, Chichester (1984).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Foces-Foces, C., Fernández-castaño, C., Claramunt, R.M. et al. Host–:Guest Properties of the Aromatic Propellene 1,4- Bis(pyrazol-1'-yl)-2,3,5,6-tetrakis(3'',5''-dimethylpyrazol-1''- yl)benzene. Journal of Inclusion Phenomena 33, 169–189 (1999). https://doi.org/10.1023/A:1008063309710
Issue Date:
DOI: https://doi.org/10.1023/A:1008063309710