The hydrophobic effect. 1. A consequence of the mobile order in H- bonded liquids

Journal of Pharmaceutical Sciences

Volumn 87, Issue 8, 1998, Pages 987-997

  Ruelle, Paul ^a   Kesselring, Ulrich W ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE; ALCOHOL; BENZOCAINE; BENZOIC ACID; BUTANOL; BUTYLCAINE; CAFFEINE; CAMPHOR; EPHEDRINE; ESTRADIOL; ESTRONE; ETHYLENE GLYCOL; FORMAMIDE; HYDROCORTISONE; HYDROCORTISONE ACETATE; LIDOCAINE; LOCAL ANESTHETIC AGENT; METHANOL; PARACETAMOL; PHENAZONE; PHENYLBUTAZONE; PROPANOL; PROPYLCAINE; PROPYLENE GLYCOL; STEROID; TESTOSTERONE PROPIONATE; THEOBROMINE; THEOPHYLLINE; TRIAMCINOLONE DIACETATE; UNINDEXED DRUG;

ARTICLE; DRUG SOLUBILITY; ENTROPY; HYDROGEN BOND; HYDROPHOBICITY; PHYSICAL CHEMISTRY; THERMODYNAMICS;

EID: 0031828748     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js970205e     Document Type: Article

References (121)

1. Frank, H. S.; Evans, M. W. Free volume and entropy in condensed systems. III Entropy in binary liquid mixtures; partial molar entropy in dilute solutions; structure and thermodynamics in aqueous electrolytes. J. Chem. Phys. 1945, 13, 507-532.
2. Kauzmann, W. Some factors in the interpretation of protein denaturation. Adv. Protein Chem. 1959, 14, 1-63.
3. Nemethy, G.; Sheraga, H. A. Structure of water and hydrophobic bonding in proteins. II. Model for the thermodynamic properties of aqueous solutions of hydrocarbons. J. Chem. Phys. 1962, 36, 3401-3417.
4. Hermann, R. B. Theory of hydrophobic bonding. 1. The solubility of hydrocarbons in water within the context of the significant structure theory of liquids. J. Phys. Chem. 1971, 75, 363-368.
5. Hermann, R. B. Theory of hydrophobic bonding. 2. The correlation of hydrocarbon solubility in water with solvent cavity surface area. J. Phys. Chem. 1972, 76, 2754-2759.
6. Dashevsky, V. G.; Sarkisov, G. N. The solvation and hydrophobic interaction of nonpolar molecules in water in the approximation of interatomic potentials: the Monte Carlo method. Mol. Phys. 1974, 27, 1271-1290.
7. Pratt, L. R.; Chandler, D. Theory of the hydrophobic effect. J. Chem. Phys. 1977, 67, 3683-3704.
8. Tanford, C. The hydrophobic effect: formation of micelles and biological membranes, 2nd ed.; Wiley-Interscience: New York, 1980.
9. Mirejovsky, D.; Arnett, E. M. Heat capacities of solution for alcohols in polar solvents and the new view of hydrophobic effects. J. Am. Chem. Soc. 1983, 105, 1112-1117.
10. Privalov, P. L.; Gill, S. J. Stability of protein structure and hydrophobic interaction. Adv. Protein Chem. 1988, 39, 191-234.
11. Privalov, P. L.; Gill, S. J. The hydrophobic effects: A reappraisal. Pure Appl. Chem. 1989, 61, 1097-1104.
12. Muller, N. Search for a realistic view of hydrophobic effects. Acc. Chem. Res. 1990, 23, 23-28.
13. Breslow, R. Hydrophobic effects on simple organic reactions in water. Acc. Chem. Res. 1991, 24, 159-164.
14. Costas, M.; Kronberg, B.; Silveston, R. General thermodynamic analysis of the dissolution of nonpolar molecules into water. J. Chem. Soc., Faraday Trans. 1994, 90, 1513-1522.
15. Blokzijl, W.; Engberts, J. B. F. N. Hydrophobic effects. opinion and facts. Angew. Chem., Int. Ed. Engl. 1993, 32, 1545-1579.
16. Alger, D. B. Erroneous explanations for the limited water solubility of organic liquids. J. Chem. Educ. 1994, 71, 281.
17. Madan, B.; Lee B. Role of hydrogen bonds in hydrophobicity: the free energy of cavity formation in water models with and without hydrogen bonds. Biophys. Chem. 1994, 51, 279-289.
18. Kier, L. B.; Cheng, C.-K.; Testa, B.; Carrupt, P.-A. A cellular automata model of the hydrophobic effect. Pharm. Res. 1995, 12, 615-620.
19. Lee, B.; Graziano, G. A two-state model of hydrophobic hydration that produces compensating enthalpy and entropy changes. J. Am. Chem. Soc. 1996, 118, 5163-5168.
20. Mancera, R. L. Towards an understanding of the molecular basis of hydrophobicity. J. Comput.-Aided Mol. Design 1996, 10, 321-326.
21. Wallqvist, A.; Covell, D. G. On the origin of the hydrophobic effect: observations from simulations of n-dodecane in model solvents. Biophys. J. 1996, 71, 600-608.
22. SanRoman-Zimbron, M. L.; Ortega-Blake, I. On the molecular basis of hydrophobicity: a Monte Carlo study of propionic acid hydration. J. Chem. Phys. 1997, 107(8), 3253-3261.
23. Desehenes, L. A.; Zilaro, P.; Muller, L. J.; Fourkas, J. T.; Mohanty, U. Quantitative measure of hydrophobicity: experiment and theory. J. Phys. Chem. B 1997, 101, 5777-5779.
24. Sharp, K. A.; Madan, B. Hydrophobic effect, water structure, and heat capacity changes. J. Phys. Chem. B 1997, 101, 4343-4348.
25. Vailaya, A.; Horváth, C. Solvophobic theory and normalized free energies of nonpolar substances in reversed phase chromatography. J. Phys. Chem. B 1997, 101, 5875-5888.
26. Ben Naim, A. Water and aqueous solutions; Plenum: New York, 1974.
27. Stillinger, F. H. Structure in aqueous solutions of nonpolar solutes from the standpoint of scaled-particle theory. J. Solut. Chem. 1973, 2, 141-158.
28. Pierrotti, R. A. Aqueous solutions of nonpolar gases. J. Phys. Chem. 1965, 69, 281-288.
29. Hermann, R. B. Calculation of hydrophobic interactions from molecular dynamics, surface areas, and experimental hydrocarbon solubilities. J. Comput. Chem. 1993, 14, 741-750.
30. Tanaka, H. Integral equation and Monte Carlo study on hydrophobic effects: size dependence of apolar solutes on solute-solute interactions and structures of water. J. Chem. Phys. 1987, 86, 1512-1520.
31. Pohorille, A.; Pratt, L. R. Cavities in molecular liquids and the theory of hydrophobic solubilities. J. Am. Chem. Soc. 1990, 112, 5066-5074.
32. Kronberg, B.; Costas, M.; Silveston, R. Understanding the hydrophobic effect. J. Dispers. Sci. Technol. 1994, 15, 333-351.
33. Shinoda, K.; Fujihira, M. The analysis of the solubility of hydrocarbons in water. Bull. Chem. Soc. Jpn. 1968, 41, 2612-2615.
34. Shinoda, K. Icerberg formation and solubility. J. Phys. Chem. 1977, 81, 1300-1302.
35. Hvidt, A. The solubility of hydrocarbons in water. Acta Chem. Scand. 1983, 37, 99-103.
36. Patterson, D.; Barbe, M. Enthalpy-entropy compensation and order in alkane and aqueous systems. J. Phys. Chem. 1976, 80, 2435-2436.
37. Funasaki, N.; Hada, S.; Neya, S.; Machida, K. Cavity surface areas and solubilities of alkanes in water. J. Colloid Interface Sci. 1985, 106, 255-258.
38. Reynolds, J. A.; Gilbert, D. B.; Tandford, C. Empirical correlation between hydrophobic free energy and aqueous cavity surface area. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 2925-2927.
39. Leo, A.; Hansch, C.; Jow, P. Y. C. Dependence of hydrophobicity of apolar molecules on their molecular volume. J. Med. Chem. 1976, 19, 611-615.
40. Abraham, M. H. Thermodynamics of solution of homologous series of solutes in water. J. Chem. Soc., Faraday Trans. 1. 1984, 80, 153-181.
41. Seidell, A. Solubilities of organic compounds, 3rd ed.; Van Nostrand: New York, 1941; Vol. 2.
42. 7, Solubility Data Series; Kertes, A. S., Ed.; Pergamon: New York, 1989; Vol. 37.
43. 36, Solubility Data Series; Kertes, A. S., Ed.; Pergamon: New York, 1989; Vol. 38.
44. Somsen, G. The Energy of intermolecular interactions in solution. In Intermolecular Forces; Huyskens, P. L.; Luck, W. A. P.; Zeegers-Huyskens, T., Eds.; Springer-Verlag: Berlin, 1991; pp 367-386.
45. Turner, J.; Soper, A. K.; Finney, J. L. A neutron-diffraction study of tetramethylammonium chloride in aqueous solution. Mol. Phys. 1990, 70, 679-700.
46. Turner, J.; Soper, A. K.; Finney, J. L. Water structure in aqueous solutions of tetramethylammonium chloride. Mol. Phys. 1992, 77, 411-429.
47. Finney, J. L.; Soper, A. K.; Turner, J. Z. Water perturbation close to nonpolar groups in aqueous solutions. Pure Appl. Chem. 1993, 65, 2521-2526.
48. Guillot, B.; Guissani, Y. Physical chemistry of aqueous systems; White, H. J., Sengers, J. V., Newmann, D. B.; Bellows, J. C., Eds.; Begell House: New York, 1995; p 269.
49. Vaisman, I.I.; Brown, F. K.; Tropsha, A. Distance dependence of water structure around model solutes. J. Phys. Chem. 1994, 98, 5559-5564.
50. Turner, J.; Soper, A. K. The effect of apolar solutes on water structure: alcohols and tetraalkylammonium ions. J. Chem. Phys. 1994, 101, 6116-6125.
51. Finney, J. L.; Soper, A. K.; Turner, J. Physical chemistry of aqueous systems; White, H. J., Sengers, J. V.; Newmann, D. B.; Bellows, J. C., Eds.; Begell House: New York, 1995; p 468.
52. Re, M.; Laria, D.; Fernandez-Prini, R. The role of solvent structure in perturbation methods applied to the dissolution of an apolar solute in water. Ber. Bunsen-Ges. Phys. Chem. 1996, 700, 1328-1334.
53. Huyskens, P. L.; Haulait-Pirson, M. C. A new expression for the combinatorial entropy of mixing in liquid mixtures. J. Mol. Liquids 1985, 31, 135-151.
54. Huyskens, P. L.; Siegel, G. G. Fundamental question about entropy. Bull. Soc. Chim. Belg. 1988, 97, 809-830.
55. Huyskens, P. L. Mobile and static molecular disorder in liquids. J. MoL Struct. 1992, 274, 223-246.
56. Huyskens, P. L.; Seghers, K.; Morissen, H. Estimation of the molar free energy of melting of crystals from solubility data according to the theory of the mobile disorder. Fluid Phase Equil. 1994, 96, 1-18.
57. Scatchard, G. Equilibria in nonelectrolyte solutions in relation to the vapor pressures and densities of the components. Chem. Rev. 1931, 8, 321-332.
58. Berthelot, M. Sur le mélange de gaz. Compt. Rend. Acad. Sci. 1898, 126, 1703-1706.
59. Chastrette, M.; Crétin, D. Structure-property relationships determination of the vapor pressure of hydrocarbon and oxygenated compounds using multifunctional autocorrelation method (MAM). SAR QSAR Environ. Res. 1995, 3, 131-149.
60. Ambrose, D.; Eilender, J. H.; Sprake, C. H. S.; Townsend, R. Thermodynamic properties of organic oxygen compounds. XLIII. Vapour pressures of some ethers. J. Chem. Thermodyn. 1976, 8, 165-178.
61. Luck, W. A. P. A model for hydrogen-bonded liquids. Angew. Chem., Int. Ed. Engl. 1980, 19, 28-41.
62. Furth, R. In Investigation on the theory of brownian motion; Dover: New York, 1956.
63. Hurst, G. S.; Payne, M. G. Principles and applications of resonance ionization spectroscopy; Hilger: Bristol, 1988; p 196.
64. Redlich, O.; Kister, A. T. On the thermodynamics of non-electrolyte solutions and its technical applications. III. Systems with associated components. J. Chem. Phys. 1947 15, 849-855.
65. Kempter, H.; Mecke, R. Spectroscopic determination of association equilibrium. Z. Phys. Chem. B 1940, 46, 229-241.
66. Prigogine I.; Bellemans, A.; Mathot, V. The molecular theory of solutions; North-Holland: Amsterdam, 1957.
67. Wiehe, I. A.; Bagley, E. B. Thermodynamic properties of solutions of alcohols in inert solvents. Ind. Eng. Chem Fundam. 1967, 6, 209-217.
68. Kretschmer, C. B.; Wiebe, R. Thermodynamics of alcohol-hydrocarbon mixtures. J. Chem. Phys. 1954, 22, 1697-1701.
69. Kehiaian, H.; Treszczanovicz, A. Sur la thermodynamique des mélanges associés. Bull. Soc. Chim. France 1969, 18, 1561-1568.
70. Nagata, I.; Kawamura, Y. Thermodynamics of alcohol-unassociated active component liquid mixtures. Chem. Eng. Sci. 1979, 34, 601-611.
71. Wilhoit, R. C.; Zwolinski, B. J. Physical and thermodynamic properties of aliphatic alcohols. J. Phys. Chem. Ref. Data 1973, 2 (suppl. 1), 1-429.
72. Rossini, F. D.; Pitzer, K. S.; Arnett, R. L.; Braun, R. M.; Pimentel, G. C. Selected values of physical and Thermodynamic properties of hydrocarbons and related compounds; Carnegie: Pittsburgh, 1953.
73. Huyskens, P. L. Interaction of water in ionic and nonionic hydrates; Kleeberg, H., Ed.; Springer-Verlag: Berlin, 1987; p 123.
74. Ruelle, P.; Rey-Mermet, C.; Buchmann, M.; Ho, N.-T.; Kesselring, U. W.; Huyskens, P. L. A new predictive equation for the solubility of drugs based on the thermodynamics of mobile disorder. Pharm. Res. 1991, 8, 840-850.
75. 70 in seven normal alcohols and their deduced solubility in water. Fullerene Sci. Technol. 1996, 4(3), 509-515.
76. Domanska, U.; Fofman, T.; Rolinska, J. Solubility and vapour pressures in saturated solutions of high-molecular-weight hydrocarbons. Fluid Phase Equilib. 1987, 32, 273-293.
77. Ashkinazi, L. A.; Panichkina, O. M.; Ravdel, A. A.; Slobodin, Ya. M. Solubility of adamantane and its analogues. Zhurnal Prikladnoi Khimii 1982, 55, 807-811.
78. Dickhut, R. M.; Andren, A. W.; Armstrong, D. E. Naphthalene solubility in selected organic solvent/water mixtures. J. Chem. Eng. Data 1989, 34, 438-443.
79. The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals, 11th ed.; Budavari, S., Ed.; Merck & Co.: Rahway, NJ, 1989.
80. Hildebrand, J. H.; Ellefson, E. T.; Beebe, C. W. Solubilities of anthracene, anthraquinone, parabromobenzene, phenanthrene and iodine in Various Solvents. J. Am. Chem. Soc. 1917, 39, 2301-2302.
81. Powell, J. R.; McHale, M. E. R.; Kauppila, A.-S. M.; Acree, W. E., Jr.; Campbell, S. W. Solubility of anthracene in binary alcohol + 1-pentanol solvent mixtures at 25°C: comparison of expressions derived from mobile order theory and the Kretschmer-Wiebe association model. J. Solut. Chem. 1996, 25, 1001-1017.
82. Mackay D.; Shiu, W. Y. Aqueous solubility of polynuclear aromatic hydrocarbons. J. Chem. Eng. Data 1977, 22, 309-402.
83. Powell, J. R.; Voisinet, D.; Salazar, A.; Acree, W. E., Jr. Solubility of pyrene in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon mobile order theory. Phys. Chem. Liq. 1994, 28, 269-276.
84. Kühne, R.; Ebert, R.-U., Kleint, F.; Schmidt, G.; Schüürmann, G. Group contribution methods to estimate water solubility of organic chemicals. Chemosphere 1995, 30, 2061-2077.
85. Fletcher, K. A.; McHale, M. E. R.; Coym, K. S.; Acree, W. E., Jr. Solubility of trans-stilbene in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon mobile order theory. Can. J. Chem. 1997, 75, 258-261.
86. Fletcher, K. A.; McHale, M. E. R.; Coym, K. S.; Acree, W. E., Jr. Solubility of thianthrene in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon mobile order theory. Phys. Chem. Liq. 1997, 34, 41-49.
87. Fletcher, K. A.; Coym, K. S.; Roy, L. E.; Hernández, C. E., McHale, M. E. R.; Acree, W. E., Jr. Solubility of thioxanthen-9-one in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon mobile order theory. Phys. Chem. Liq. 1998, 35, 243-252.
88. Garland, F. M.; Hoerr, C. W.; Pool, W. O.; Ralston, A. W. Solubilities of high molecular weight symmetrical normal aliphatic ketones. J. Org. Chem. 1943, 8, 344-357.
89. Ruelle, P.; Sarraf, E.; Van Den Berge, L.; Seghers, K.; Buchmann, M.; Kesselring, U. W. The effect of proton-acceptor sites of the solute on its solubility in proton-donor solvents. Pharm. Acta Helv. 1993, 68, 49-60.
90. Sedgwick, R. S.; Hoerr, C. W.; Harwood, H. J. Solubilities of saturated fatty acid esters. J. Org. Chem. 1952, 17, 327-337.
91. Krop, H. B.; van Velzen, M. J. M.; Parsons, J. R.; Govers, H. A. J. n-Octanol-water partition coefficients, aqueous solubilities and Henry's law constants of fatty acid esters. Chemosphere 1997, 34, 107-119.
92. James, K. C.; Roberts, M., The solubilities of the lower testosterone esters. J. Pharm. Pharmcol. 1968, 20, 709-714.
93. Ruchelman, W. M. Solubility studies of estrone in organic solvents using gas-liquid chromatography. Anal. Biochem. 1967, 19, 98-108.
94. Salole, E. G. The physicochemical properties of oestradiol. J. Pharm. Biomed. Anal. 1987, 5, 635-648.
95. Lundberg, B. Temperature effect on the water solubility and water-octanol partition of some steroids. Acta Pharm. Sueca. 1979, 16, 151-158.
96. Remington's pharmaceutical sciences; Gennaro, A. R., Ed.; Mack Publishing: Easton, PA, 1985.
97. Hagen, T. A. Physicochemical study of hydrocortisone and hydrocortisone n-alkyl-21-esters. Ph.D. Thesis, University of Michigan, 1979.
98. The Martindale, The Extra Pharmacopeia; Reynolds, E. F., Ed.; The Pharmaceutical Press: London, 1993.
99. Yalkowsky, S. H.; Valvani, S. C. Solubility and partitioning. I. Solubility of nonelectrolytes in water. J. Pharm. Sci. 1980, 69, 912-922.
100. Hagen, T. A.; Flynn, G. L. Solubility of hydrocortisone in organic and aqueous media. Evidence for regular solution behavior in apolar solvents. J. Pharm. Sci. 1983, 72, 409-414.
101. Flynn, G. L.; Shah, Y.; Prakongpan, S.; Kwan, K. H.; Higuchi, W. I.; Hofman, A. F. Cholesterol solubility in organic solvents. J. Pharm. Sci. 1979, 68, 1090-1097.
102. Bar, L.-K.; Garti, N.; Sarig, S.; Bar, R. Solubilities of cholesterol, sitosterol and cholesteryl acetate in polar organic solvents. J. Chem. Eng. Data 1984, 29, 440-443.
103. Lin, H.-M.; Nash, R. A. An experimental method for determining the Hildebrand solubility parameter of organic nonelectrolytes. J. Pharm. Sci. 1993, 82, 1018-1025.
104. Aalto, T. R., Firman, M. C.; Rigler, N. E. p-Hydroxybenzoic acid esters as preservatives. I. Uses, antibacterial and antifungal studies, properties and determination. J. Am. Pharm. Assoc. 1953, 42, 449-457.
105. Alexander, K. S., Mauger, J. W.; Petersen H., Jr.; Paruta, A. N. Solubility profiles and thermodynamics of parabens in aliphatic alcohols. J. Pharm. Sci. 1977, 66, 42-48.
106. Restaino F. A.; Martin, A. N. Solubility of benzoic acid and related compounds in a series of n-alkanols. J. Pharm. Sci. 1964, 53, 636-639.
107. Beerbower, A.; Wu, P. L.; Martin, A. Expanded solubility parameter approach. I: Naphthalene and benzoic acid in individual solvents. J. Pharm. Sci. 1984, 73, 179-188.
108. Martin, A.; Wu, P. L.; Beerbower, A. Expanded solubility parameter approach. II: p-Hydroxybenzoic acid and methyl p-hydroxybenzoate in individual solvents. J. Pharm. Sci. 1984, 73, 188-194.
109. Gharavi, M.; James, K. C.; Sanders, L. M. Solubilities of mestanolone, methanedienone, methyltestosterone, nandrolone, and testosterone in homologous series of alkanes and alkanols. Int. J. Pharm. 1983, 14, 333-341.
110. Bowen, D. B.; James, K. C.; Roberts, M. An investigation of the distribution coefficients of some androgen esters using paper chromatography. J. Pharm. Pharmacol. 1970, 22, 518-522.
111. Reuteler-Faoro, D. Etude critique de deux méthodes de détermination des paramètres de cohésion partiels caractérisant des substances pharmaceutiques solides. Ph.D. Thesis, University of Lausanne, School of Pharmacy, Lausanne (Switzerland), 1989.
112. Barra, J.; Lescure, F.; Doelker, E.; Bustamante, P. The expanded Hansen approach to solubility parameters. Paracetamol and citric acid in individual solvents. J. Pharm. Pharmacol. 1997, 49, 644-651.
113. Romero, S.; Reillo, A.; Escalera, B.; Bustamante, P. The behavior of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents. Relationship to solubility curves to specific and nonspecific interactions. Chem. Pharm. Bull. 1996, 44(5), 1061-1064.
114. Subrahmanyam, C. V. S.; Sreenivasa, M.; Venkata Rao, J.; Gundu Rao, P. Irregular solution behaviour of paracetamol in binary solvents. Int. J. Pharm. 1992, 78, 17-24.
115. Suzuki, T. Development of an automatic estimation system for both the partition coefficient and aqueous solubility. J. Comput.-Aided Mol. Design 1991, 5, 149-166.
116. Schwartz, P.; Paruta, A. N. Solution thermodynamics of alkyl p-aminobenzoates. J. Pharm. Sci. 1976, 65, 252-257.
117. Paruta, A. N. Thermodynamics of aqueous Solutions of alkyl p-aminobenzoates. Drug. Dev. Ind. Pharm. 1984, 10(3), 453-465.
118. Martin, A.; Paruta, A. N.; Adjei, A. Extended Hildebrand solubility approach: methylxanthines in mixed solvents. J. Pharm. Sci. 1981, 70, 1115-1120.
119. Rey-Mermet, C. Determination of partial cohesion parameters from binary thermodynamic quantities. Ph.D. Thesis, University of Lausanne, School of Pharmacy, Lausanne (Switzerland), 1989.
120. Paruta, A. N. Solubility profiles for antipyrine and aminopyrine in hydro alcoholic solutions. J. Pharm. Sci. 1967, 56, 1565-1569.
121. Abraham, M. H.; Grellier, P. L.; McGill, R. A. A quantitative measure of solvent solvophobic effect. J. Chem. Soc., Perkin Trans. 2 1988, 339-345.