Abstract
Solubility and apparent molar volume data are used to demonstrate effects of amide alkylation on amide-water interactions at 25° C. Precise measurements were made of the apparent molar volumes of the amides in binary amide-water mixtures using a dilatometric technique. The results show that the apparent molar volumes of alkyl-substituted amides in water pass through a minimum at an amide concentration which varies inversely with the degree of alkylation. Further studies showed that the solubilities of methyl paraben (methyl-p-hydroxybenzoate) and naphthalene in various amide-water solvent systems increased in characteristic fashion with amide alkylation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
W. L. Hayton, D. E. Guttman, and G. Levy,J. Pharm. Sci. 61, 356 (1972).
P. H. Elworthy and H. E. C. Worthington,J. Pharm. Pharmacol. 20, 830 (1968).
C. McDonald,J. Pharm. Pharmacol. 22, 10 (1970).
P. Assarsson and F. R. Eirich,J. Phys. Chem. 72, 2710 (1968).
P. Assarsson and F. R. Eirich,Adv. Chem. 84, 1 (1968).
H. E. Wirth, R. E. Lindstrom, and J. N. Johnson,J. Phys. Chem. 67, 2339 (1963).
R. E. Lindstrom and H. E. Wirth,J. Phys. Chem. 73, 218 (1969).
A. R. Giaquinto, Ph.D. Dissertation, The University of Connecticut, 1972, Number 73-9827, University Microfilms, Ann Arbor, Michigan.
H. S. Frank and M. W. Evans,J. Chem. Phys. 13, 507 (1945).
H. S. Frank and W. Y. Wen,Disc. Faraday Soc. 24, 133 (1957).
W. Y. Wen and S. Saito,J. Phys. Chem. 68, 2639 (1964);69, 3569 (1965).
F. Franks,Ann. N. Y. Acad. Sci. 125, 277 (1965).
T. R. Hoover,J. Phys. Chem. 73, 57 (1969).
F. Franks, inPhysico-Chemical Processes in Mixed Aqueous Solvents (American Elsevier, New York, 1969), Chap. 2, p. 50.
I. M. Klotz and J. S. Franzen,J. Am. Chem. Soc. 84, 3641 (1962).
H. E. Wirth,J. Phys. Chem. 71, 2922 (1967).
H. E. Wirth and A. LoSurdo,J. Phys. Chem. 72, 751 (1968).
W. Y. Wen,J. Solution Chem. 2, 253 (1973).
M. Rabinovitz and A. Pines,J. Chem. Soc. B, 1110 (1968).
W. Kauzmann,Adv. Protein Chem. 14, 1 (1959).
T. M. Birshtein, inWater in Biological Systems, L. P. Kayuskin, ed. (Consultants Bureau, New York, 1969).
J. E. Desnoyers, G. E. Pelletier, and C. Jolicoeur,Can. J. Chem. 43, 3232 (1965).
R. E. Diamond,J. Phys. Chem. 67, 2513 (1963).
F. J. Millero,J. Phys. Chem. 72, 3209 (1968).
G. R. Leader and J. F. Gormley,J. Am. Chem. Soc. 73, 5731 (1951).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Giaquinto, A.R., Lindstrom, R.E., Swarbrick, J. et al. Amide-water interactions in cosolvent systems. I. Solubilities and apparent molar volumes of methyl paraben. J Solution Chem 6, 687–701 (1977). https://doi.org/10.1007/BF00645885
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00645885