Abstract
The interaction in water of urea, monomethylurea, monoethylurea, monopropylurea, and monobutylurea with α-cyclodextrin(hexacycloamylose) was studied calorimetrically at 25°C. The results show that the last three substances form inclusion complexes with α-cyclodextrin. The enthalpy and the association constants relative to the inclusion process were determined. The association constant values are low, indicating weak complexing that increases with increasing length of the alkyl chain. Urea and monomethylurea, on the other hand, do not form inclusion complexes. For these systems the calorimetric data were treated in terms of excess enthalpies, and the McMillan-Mayer approach was used to get an insight into the weak, non-bonding molecular interactions occurring in these solutions.
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References
W. Saenger,Angew. Chem. Int. Ed. Engl. 19, 344 (1980).
E. A. Lewis and L. D. Hansen,J. Chem. Soc. Perkin Trans. II, 2081 (1973).
R. J. Bergeron, M. A. Channing, G. J. Gibeily, and D. M. Pillor,J. Am. Chem. Soc. 99, 5146 (1977).
I. Tabushi, Y. Kiyosuka, T. Sugimoto, and K. Yamamura,J. Am. Chem. Soc. 100, 916 (1978).
P. C. Manor and W. Saenger,Nature 237, 392 (1972).
P. C. Manor and W. Saenger,J. Am. Chem. Soc. 96, 3630 (1974).
B. Hingerty and W. Saenger,J. Am. Chem. Soc. 98, 3357 (1975).
W. Saenger, M. Noltemeyer, P. C. Manor, B. Hingerty, and B. Klar,Bioorg. Chem. 5, 187 (1976).
M. Eftink and R. Biltonen, in A. Beezer,Biological Microcalorimetry, (Academic Press, London, 1980).
W. G. McMillan Jr. and J. E. Mayer,J. Chem. Phys. 13, 276 (1945).
J. J. Kozak, W. S. Knight, and W. Kauzmann,J. Chem. Phys. 48, 675 (1968).
H. L. Friedman and C. V. Krishnan,J. Solution Chem. 2, 119 (1973).
J. E. Desnoyers, G. Perron, L. Avédikian, and J. P. Morel,J. Solution Chem. 5, 631 (1976).
F. Franks, M. D. Pedley, and D. S. Reid,J. Chem. Soc. Faraday Trans. I 72, 359 (1976).
T. H. Lilley and R. P. Scott,J. Chem. Soc. Faraday Trans. I 72, 184 (1976).
J. J. Savage and R. H. Wood,J. Solution Chem. 6, 733 (1976).
G. Barone, G. Castronuovo, P. Del Vecchio, V. Elia, and M. Muscetta, submitted for publication.
G. Barone, G. Castronuovo, V. Elia, and A. Menna,J. Solution Chem. 8, 157 (1979).
G. Barone, G. Castronuovo, V. Crescenzi, V. Elia, and E. Rizzo,J. Solution Chem. 7, 1979 (1978).
V. Abate, G. Barone, G. Castronuovo, V. Elia, and P. Masturzo,Gazz. Chim. Ital. 111, 85 (1981).
V. Abate, G. Barone, P. Cacace, G. Castronuovo, and V. Elia,J. Mol. Liquids 27, 59 (1983).
G. Barone, P. Cacace, G. Castronuovo, and V. Elia,J. Chem. Soc. Faraday Trans. I 77, 1569 (1981).
C. van Hooidonk and J. C. A. E. Breebart-Hansen,Recl. Trav. Chim. Pays-Bas 90, 680 (1971).
R. L. van Etten, J. F. Sebastian, G. A. Clowes, and M. L. Bender,J. Am. Chem. Soc. 89, 3242 (1967).
T. S. Straub and M. L. Bender,J. Am. Chem. Soc. 94, 8881 (1972).
D. W. Griffiths and M. L. Bender,Adv. Catal. 23, 209 (1973).
M. Komiyama and M. L. Bender,J. Am. Chem. Soc. 100, 2259 (1978).
Water: A Comprehensive Treatise, Vol. 4, F. Franks, ed. (Plenum Press, New York, 1975).
V. Abate G. Barone, G. Castronuovo, V. Elia, and V. Savino,J. Chem. Soc. Faraday Trans. I 80, 759 (1984).
G. Barone, G. Castronuovo, V. Elia, Kh. Stassinopoulou, and G. Della Gatta,J. Chem. Soc. Faraday Trans. I 80, 3095 (1984).
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Barone, G., Castronuovo, G., Elia, V. et al. Interaction of urea and urea derivatives with cyclohexamylose in aqueous solutions at 25°C. J Solution Chem 15, 129–140 (1986). https://doi.org/10.1007/BF00646284
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DOI: https://doi.org/10.1007/BF00646284