Abstract
Crown ether complexes of six-membered N-heteroaromatic cations and the closely related bicyclic purinium cation (6) have been studied by 1H NMR, mass spectrometric and crystallographic methods. The stability constants for the complexes were determined by 1H NMR titration in acetonitrile solution and the complexation stoichiometry by 1H NMR and ESI mass spectrometric methods. Altogether six crystal structures of complexes were determined to study the complexation in the solid state. Hydrogen bonding was observed to be the most important interaction for the complexation both in solution and in the solid state but π–π interactions also contribute to it. All crystal structures of the DB18C6 complexes with six-membered N-heteroaromatic cations, except for 4-hydroxypyridinium, are isomorphous to previously studied five-membered N-heteroaromatic cations and pyridinium complexes. Such a close resemblance is not observed in B18C6 and 18C6 complexes or DB18C6ċpurinium (6).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E. Weber and F. Vögtle: in J. L. Atwood, J. E. D. Davies, D. D. Mac-Nicol and F. Vögtle (eds.), Comprehensive Supramolecular Chemistry Vol. 2, Elsevier, Oxford, 1st ed. (1996), pp. 1-28.
J. Rebek, Jr. and D. Nemeth: J. Am. Chem. Soc. 107, 6738 (1985).
J. Rebek, Jr., B. Askew, M. Killoran, D. Nemeth and F.T. Lin: J. Am. Chem. Soc. 109, 2426 (1987).
J. Rebek, Jr., L. Marshall, R. Wolak, K. Parris, M. Killoran, B. Askew, D. Nemeth, and N. Islam: J. Am. Chem. Soc. 107, 7476 (1985).
M. Berthelot, C. Laurence, M. Safar and F. Besseau: J. Chem. Soc., Perkin Trans. 2, 283 (1998).
M. Orbán, A. Kiss, and L. Barcza: J. Chem. Soc., Perkin Trans. 2, 283 (1998).
O. Kasende and T. Zeegers-Huyskens: J. Phys. Chem. 88, 2132 (1984).
C. V. Rama Rao, C. Jacob, and A.K. Chandra: J. Chem. Soc., Faraday Trans. 1 78, 3025 (1982).
M. Lämsä, J. Pursiainen, K. Rissanen, and J. Huuskonen: Acta Chem. Scand. 52, 563 (1998).
M. Lämsä, T. Suorsa, J. Pursiainen, J. Huuskonen, and K. Rissanen: Chem. Commun., 1443 (1996).
M. Lämsä, J. Huuskonen, K. Rissanen, and J. Pursiainen: Chem. Eur. J. 4, 84 (1998).
S. Kiviniemi, A. Sillanpää, M. Nissinen, K. Rissanen, M. T. Lämsä, and J. Pursiainen: Chem. Commun., 897 (1999).
S. Kiviniemi, M. Nissinen, M. T. Lämsä, J. Jalonen, K. Rissanen, and J. Pursiainen: New J. Chem. 24, 47 (2000); corr. New J. Chem. 24, 647 (2000).
D.D. Perrin, W.L.F. Armarego, and D.R. Perrin: in Purification of Laboratory Chemicals, 3rd ed., Pergamon, Oxford (1988).
Z. Otwinowski and W. Minor: in C.W. Carter, Jr. and R.M. Sweet (eds.), Methods in Enzymology, Macromolecular Crystallography, Part A, Academic Press, New York, (1997), pp. 307-326.
G.M. Sheldrick: SHELXS-97, A Program for Automatic Solution of Crystal Structures, University of Göttingen, Germany (1997).
G.M. Sheldrick: SHELXL-97, A Program for Crystal Structure Refinement, University of Göttingen, Germany, (1997).
H. Bredereck, R. Gompper R., and H. Herling: Chem. Ber. 91, 2832 (1958). /del>
N. Whittaker: J. Chem. Soc., 1646 (1953).
R. Daniels and C.G. Kormendy: J. Org. Chem. 27, 1860 (1962).
H.A. Benesi and J.H. Hildebrand: J. Am. Chem. Soc. 71, 2703 (1949).
K.A. Connors: in Binding Constants, John Wiley & Sons, New York (1987), pp. 189-200.
T.L. Gilchrist: in Heterocyclic Chemistry, Pitman, Liverpool (1984), pp. 306-309.
M. Nissinen, S. Kiviniemi, K. Rissanen, and J. Pursiainen: Cryst. Eng. Commun., no. 18 (2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kiviniemi, S., Nissinen, M., Kolli, T. et al. Crown Ether Complexes of Six-Membered N-heteroaromatic Cations. Journal of Inclusion Phenomena 40, 153–159 (2001). https://doi.org/10.1023/A:1011176602813
Issue Date:
DOI: https://doi.org/10.1023/A:1011176602813