Abstract
Complex formation between 15-crown-5 and malononitrile was studied in twelve solvents by calorimetry. Thermodynamic parameters for the crown ether adduct were determined and used in a LFER analysis to ascertain the solvent effects on the complexation process. Enthalpy of solution data show that malononitrile is solvated by electron pair donation by the solvents and the crown ether is solvated by donating electron pairs to the solvents. The complex is more solvated than the monomers.
Similar content being viewed by others
References
H.-J. Schneider, R. Kramer, S. Simova, and U. Schneider,J. Am. Chem. Soc. 110, 6442 (1988).
K. T. Chapman and W. C. Still,J. Am. Chem. Soc. 111, 3075 (1989).
D. B. Smithrud and F. Diederich,J. Am. Chem. Soc. 112 339 (1990).
J. N. Spencer, T. F. Ganunis, A. I. Zafar, C. M. Salata, S. Gupta, S. Puppala, H. J. Eppley, J. L. Ealy, and C. H. Yoder,J. Phys. Chem. 95, 4910 (1991).
J. N. Spencer, A. I. Zafar, T. F. Ganunis, C. H. Yoder, L. J. Fenton, J. L. Ealy, S. Gupta, C. M. Salata, I. M. Paul, W. J. Nicholson, and J. E. Mihalick,J. Phys. Chem. 96, 3475 (1992).
V. Gutmann,The Donor-Acceptor Approach to Molecular Interactions (Plenum, New York, 1978).
J. H. Hildebrand, J. M. Prausnitz, and R. L. Scott,Regular and Related Solutions (Van Nostrand-Reinhold, Princeton, 1970).
M. H. Abraham, G. S. Whiting, R. M. Doherty, and W. J. Shively,J. Chromatogr. 587, 213; 229 (1991).
R. W. Taft and M. J. Kamlet,J. Chem. Soc. Perkin II 1723 (1978).
A. Elbasyouny, H. J. Brugge, K. von Deuten, M. Dickel, A. Knochel, K. U. Koch, J. Kopf, D. Melzev, and G. Rudolph,J. Am. Chem. Soc. 105, 6568 (1983).
C. ReichardtSolvents and Solvent Effects in Organic Chemistry (VCH, New York, 1988).
R. W. Taft, N. J. Peinta, M. J. Kamlet, and E. M. Arnett.J. Org. Chem. 46, 661 (1981).
Y. Marcus,J. Solution Chem. 13, 599 (1984).
M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, and R. W. Taft,J. Org. Chem. 48, 2877 (1983).
M. H. Abraham,Chem. Soc. Rev. 73 (1993).
C. Laurence, M. Berthelot, M. Helbert and S. Sraidi.J. Phys. Chem 93, 3799 (1989).
M. J. Kamlet, R. Doherty, R. W. Taft, and M. H. Abraham,J. Am. Chem. Soc. 105, 6741 (1983).
M. Chastrette and J. Carretto,Can J. Chem. 632, 3492 (1985).
M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, and R. W. Taft,Prog. Org. Chem. 13, 485 (1981).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Spencer, J.N., Mihalick, J.E., Paul, I.M. et al. Solvent effects on host-guest complexation. J Solution Chem 23, 711–720 (1994). https://doi.org/10.1007/BF00972717
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00972717