Thermodynamics of solutions I: Benzoic acid and acetylsalicylic acid as models for drug substances and the prediction of solubility

Pharmaceutical Research

Volumn 20, Issue 3, 2003, Pages 471-478

  Perlovich, German L ^a,b   Bauer Brandl, Annette ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

^b INSTITUTE OF SOLUTION CHEMISTRY   (Russian Federation)

Author keywords

Acetylsalicylic acid; Alcohols; Benzoic acid; Compensation effect; Organic solvents; Solubility; Solution enthalpy

Indexed keywords

ACETYLSALICYLIC ACID; ALKANOL; BENZOIC ACID; SOLVENT;

ARTICLE; CALORIMETRY; DRUG SOLUBILITY; ENERGY; ENTHALPY; ENTROPY; MULTIPLE REGRESSION; PRIORITY JOURNAL; SOLVATION; STATISTICAL ANALYSIS; THERMODYNAMICS;

ALCOHOLS; ASPIRIN; BENZOIC ACID; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHYSICAL; MATHEMATICS; MODELS, CHEMICAL; SOLUBILITY; SOLVENTS; THERMODYNAMICS;

EID: 0037335356     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022624725495     Document Type: Article

References (28)

1. J. H. Hildebrand and R. L. Scott. Solubility of Nonelectrolytes, 3rd ed., Reinhold, New York, 1950.
2. P. Flory. Thermodynamics of high polymer solutions. J. Chem. Phys. 9:660-661 (1941).
3. M. Huggins. Solution of long chain compounds. J. Chem. Phys. 9:440 (1941).
4. P. Ruelle and U. W. Kesselring. The hydrophobic effect. 1. A consequence of the mobil order in H-bonded liquids. J. Pharm. Sci. 87:987-997 (1998); The hydrophobic effect. 2. Relative importance of the hydrophobic effect on the solubility of hydrophobes and pharmaceuticals in H-bonded solvents. J. Pharm. Sci. 87:998-1014 (1998); The hydrophobic effect. 3. A key ingredient in predicting n-octanol-water partition coefficients. J. Pharm. Sci. 87:1015-1024 (1998).
5. P. Ruelle and U. W. Kesselring. The hydrophobic effect. 1. A consequence of the mobil order in H-bonded liquids. J. Pharm. Sci. 87:987-997 (1998); The hydrophobic effect. 2. Relative importance of the hydrophobic effect on the solubility of hydrophobes and pharmaceuticals in H-bonded solvents. J. Pharm. Sci. 87:998-1014 (1998); The hydrophobic effect. 3. A key ingredient in predicting n-octanol-water partition coefficients. J. Pharm. Sci. 87:1015-1024 (1998).
6. P. Ruelle and U. W. Kesselring. The hydrophobic effect. 1. A consequence of the mobil order in H-bonded liquids. J. Pharm. Sci. 87:987-997 (1998); The hydrophobic effect. 2. Relative importance of the hydrophobic effect on the solubility of hydrophobes and pharmaceuticals in H-bonded solvents. J. Pharm. Sci. 87:998-1014 (1998); The hydrophobic effect. 3. A key ingredient in predicting n-octanol-water partition coefficients. J. Pharm. Sci. 87:1015-1024 (1998).
7. C. M. Hansen and K. Skaarup. Three-dimensional solubility parameter - key to paint components affinities III. Independent calculation of the parameter components. J. Paint. Technol. 39:511-514 (1967).
8. B. L. Karger, L. R. Snyder, and C. Eon. Expanded solubility parameter treatment for classification and use of chromatographic solvents and absorbents. Anal. Chem. 50:2126-2136 (1978).
9. M. J. Kamlet, J. L. M. Abboud, and R. W. Taft, Jr. An examination of linear solvation energy relationships. Progr. Org. Chem. 13:485-630 (1981).
10. B. Chawla, S. K. Pollack, C. R. Lebrilla, M. J. Kamlet, and R. W. Taft, Jr. Use of carbon-13 substituent chemical shifts to scale non-hydrogen bonding dipolar interactions of protonic solvents. J. Am. Chem. Soc. 103:6924-6930 (1981).
11. L. P. Hammett. Physical Organic Chemistry, McGraw-Hill, New York, 1970.
12. C. Reichardt. Solvent Effects in Organic Chemistry, 2nd ed., VCH, Verlag Chemie, Weinheim, 1979.
13. V. Gutmann. Solvent effects on the reactivities of organometallic compounds. Coord. Chem. Rev. 18:225-255 (1976).
14. I. A. Koppel and V. A. Palm. The influence of the solvent on organic reactivity. In Advances in Linear Free Energy Relationships. Plenum, London, 1972.
15. K. S. Alexander, J. W. Mauger, H. Petersen, Jr., and A. N. Paruta. Solubility profiles and thermodynamics of parabens in aliphatic alcohols. J. Pharm. Sci. 66:42-48 (1977).
16. J. A. Rogers and A. Wong. The temperature dependence and thermodynamics of partitioning of phenols in the n-octanol-water system. Int. J. Pharm. 6:339-348 (1980).
17. J. A. Rogers. Solution thermodynamics of phenols. Int. J. Pharm. 10:89-97 (1982).
18. E. Tomlinson. Enthalpy-entropy compensation analysis of pharmaceutical, biochemical and biological systems. Int. J. Pharm. 13:115-144 (1983).
19. A. Beerbower, P. L. Wu, and A. Martin. Expanded solubility parameter approach I: Naphthalene and benzoic acid in individual solvents. J. Pharm. Sci. 73:179-188 (1984).
20. R. A. Ho-Meei Lin Nash. An experimental method for determining the Hildebrand solubility parameter of organic nonelectrolytes. J. Pharm. Sci. 82:1018-1026 (1993).
21. V. A. Breus, F. T. Hafizov, M. D. Borisover, B. N. Solomonov, and A. I. Konovalov. Influence of the specific interaction of the carbonic acids with various proton acceptors. Rus. J. Organic Chem. 60:1147-1151 (1990).
22. W. Zielenkiewicz, G. Perlovich, and M. Wszelaka-Rylik. The vapor pressure and the enthalpy of sublimation. Determination by inert gas flow method. J. Therm. Anal. Calorimetry. 57:225-234 (1999).
23. S. H. Yalkowsky and S. C. Valvani. Solubility and partitioning I: Solubility of nonelectrolytes in water. J. Pharm. Sci. 69:912-922 (1980).
24. E. M. Arnett, L. Joris, E. Mitchell, T. S. S. R. Murty, T. M. Gorrie, and P. v. R. Schleyer. Studies of hydrogen-bonded complex formation III. Thermodynamics of complexing by infrared spectroscopy and calorimetry. J. Am. Chem. Soc. 92:2365-2377 (1970).
25. I. A. Koppel and A. I. Pai. The parameters of common basicity scale of solvents. Rus. Reaction Ability of Organic Compounds 11:121-138 (1974).
26. W. Zielenkiewicz, B. Golankiewicz, G. L. Perlovich, and M. Kozbial. Aqueous solubilities, infinite dilution activity coefficients and octanol-water partition coefficients of tricyclic analogues of acyclovir. J. Solut. Chem. 28:737-751 (1999).
27. G. L. Perlovich and A. Brandl-Bauer. The melting process of acetylsalicylic acid single crystals. J. Therm. Anal. Calorimetry 63:653-661 (2001).
28. J. D. Cox and G. Pilcher. Thermochemistry of Organic and Organometallic Compounds, Academic Press, London, 1970.