A QSPR study of the solubility of gases and vapors in water

Journal of Chemical Information and Computer Sciences

Volumn 36, Issue 6, 1996, Pages 1162-1168

  Katritzky, Alan R ^a   Mu, Lan ^a   Karelson, Mati ^b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF TARTU   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000115399     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci960081b     Document Type: Article

References (49)

1. Briggs, G. G. Theoretical and Experimental Relationships Between Soil Absorption, Octanol-Water Partition Coefficients, Water Solubilities, Bioconcentration Factors and Parachor. J. Agric. Food Chem. 1981, 29, 1050-1059.
2. Pollack, G. L. Why Gases Dissolve in Liquids. Science 1991, 251, 1323-1330.
3. c) at Rest and Work Measured Simultaneously by 3 Inert Substances. G. Ital. Med. Lav. 1993, 15, 133-138.
4. Hine, H.; Mookerjee, P. K. The Intrinsic Hydrophilic Character of Organic Compounds. Correlations in Terms of Structural Contributions. J. Org. Chem. 1975, 40, 292-298.
5. Wilhelm, E.; Battino, R.; Wilcock, R. J. Low-Pressure Solubility of Gases in Liquid Water. Chem. Rev. 1977, 77, 219-262.
6. Swope, W. C.; Andersen, H. C. A Molecular Dynamics Method for Calculating the Solubility of Gases in Liquids and the Hydrophobic Hydration of Inert-Gas Atoms in Aqueous Solution. J. Phys. Chem. 1984, 88, 6548-6556.
7. Watanabe, K.; Andersen, H. C. Molecular Dynamics Study of the Hydrophobic Interaction in an Aqueous Solution of Krypton. J. Phys. Chem. 1986, 90, 795-802.
8. - from Statistical Perturbation Theory. Chem. Phys. 1989, 129, 193-200.
9. Onsager, L. Theories of Concentrated Electrolytes. Chem. Rev. 1933 13, 73-89.
10. Kirkwood, J. G. Statistical Mechanics of Fluid Mixtures. J. Chem. Phys. 1935, 3, 300-313.
11. Pierotti, R. A. The Solubility of Gases in Liquids. J. Phys. Chem. 1963, 67, 1840-1845.
12. Crovetto, R.; Fernandez-Prini, R.; Japas, M. L. Contribution of the Cavity-Formation or Hard-Sphere Term to the Solubility of Simple Gases in Water. J. Phys. Chem. 1982, 86, 4094-4095.
13. Eley, D. D. On The Solubility of Gases. Part I. the Inert Gases in Water. Trans. Faraday Soc. 1939, 35, 1281-1293. On The Solubility of Gases. Part II. a Comparison of Organic Solvents with Water. Trans. Faraday Soc. 1939, 35, 1421-1432.
14. Eley, D. D. On The Solubility of Gases. Part I. the Inert Gases in Water. Trans. Faraday Soc. 1939, 35, 1281-1293. On The Solubility of Gases. Part II. a Comparison of Organic Solvents with Water. Trans. Faraday Soc. 1939, 35, 1421-1432.
15. Guttman, H. J.; Anderson, C. F.; Record, M. T., Jr. Analyses of Thermodynamic Data for Concentrated Hemoglobin Solutions Using Scaled Particle Theory: Implications for a Simple Two-State Model of Water in Thermodynamic Analyses of Crowding In Vitro and In Vivo. Biophys. J. 1995, 68, 835-846.
16. Braibanti, A.; Fisicaro, E.; Dallavalle, F.; Lamb, J. D.; Oscarson, J. L.; Rao, R. S. Molecular Thermodynamic Model for the Solubility of Noble Gases in Water. J. Phys. Chem. 1994, 98, 626-634.
17. Braibanti, A.; Fisicaro, E.; Ghiozzi, A.; Compari, C.; Panelli, M. Solubility of Inert Gases and Liquid Hydrocarbons in Water. J. Solution Chem. 1995, 24, 703-718.
18. Besseling, N. A. M.; Lyklema, J. Hydrophobic Hydration of Small Apolar Molecules and Extended Surfaces: A Molecular Model. Pure Appl. Chem. 1995, 67, 881-888.
19. Horvath, A. L. Molecular Design: Chemical Structure Generation from the Properties of Pure Organic Compounds; Elsevier: Amsterdam, 1992.
20. Wessel, M. D.; Jurs, P. C. Prediction of Normal Boiling Points for a Diverse Set of Industrially Important Organic Compounds from Molecular Structure. J. Chem. Inf. Comput Sci. 1995, 35, 841-850.
21. Hall, L. H.; Kier, L. B. Electrotopological State Indices for Atom Types: A Novel Combination of Electronic, Topological, and Valence State Information. J. Chem. Inf. Comput. Sci. 1995, 35, 1039-1045.
22. Sutter, J. M.; Jurs, P. C. Prediction of Aqueous solubility for a Diverse Set of Heteroatom-Containing Organic Compounds Using a Quantitative Structure-Property Relationship. J. Chem. Inf. Comput. Sci. 1996, 36, 100-107.
23. Katritzky, A. R.; Ignatchenko, E. S.; Barcock, R. A.; Lobanov, V. S.; Karelson, M. Prediction of Gas Chromatographic Retention Times and Response Factor Using a General Quantitative Structure-Property Relationship Treatment. Anal. Chem. 1994, 66, 1799-1807.
24. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. QSPR: The Correlation and Quantitative Prediction of Chemical and Physical Properties from Structure. Chem. Soc. Rev. 1995, 24, 279-287.
25. (a) Katritzky, A. R.; Mu, L.; Lobanov, V. S.; Karelson, M. The Correlation of Boiling Points with Molecular Structure. Part I: A Training Set of 298 Diverse Organics and a Test Set of 9 Simple Inorganics. J. Phys. Chem. 1996, 100, 10400-10407.
26. (b) Huibers, P. D. T.; Lobanov, V. S.; Katritzky, A. R.; Shah, D. O. and Karelson, M. Prediction of Critical Micelle Concentration Using a Quantitative Structure-Property Relationship Approach. 1. Nonionic Surfactants Langmuir 1996, 12, 1462-1470.
27. Cabani, S.; Gianni, P.; Mollica, V.; Lepori, L. Group Contributions to the Thermodynamic Properties of Non-Ionic Orgnic Solutes in Dilute Aqueous Solution. J. Solution Chem. 1981, 10, 563-595.
28. Nirmalakhandan, N. N.; Speece, R. E. QSAR Model for Predicting Henry's Constant. Environ. Sci. Technol. 1988, 22, 1349-1357.
29. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis: Wiley: New York, 1986.
30. Horvath, A. L. Halogenated Hydrocarbons; Marcel Dekker: New York, 1982.
31. Russell, C. J.; Dixon, S. L.; Jurs, P. C. Computer-Assisted Study of the Relationship Between Molecular Structure and Henry's Law Constant. Anal. Chem. 1992, 64, 1350-1355.
32. Abraham, M. H.; Andonian-Haftvan, J.; Whiting, G. S.; Leo, A.; Taft, R. S. Hydrogen Bonding. Part 34. The Factors that Influence the Solubility of Gases and Vapours in Water at 298 K, and a New Method for its Determination. J Chem. Soc., Perkin Trans. 2 1994, 1777-1791.
33. PCMODEL, 5th ed.; Serena Software: Bloomington, IN, 1992.
34. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F. and Stewart, J. J. P. AMI: A New General Purpose Quqntum Mechanical Molecular Model, J. Am. Chem. Soc. 1985, 107, 3902-3909.
35. (b) Karelson, M. M.; Tamm, T.; Katritzky, A. R.; Cato, S. J.; Zerner, M. C. M. O. Calculations Applicable to Condensed Phases: The Combination of Self-Consistent Reaction Field Theory with Semi-Empirical Quantum-Chemical Methods. Tetrahedron Comput. Methodol. 1989, 2, 295-304.
36. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. CODESSA Training Manual; 1995.
37. Rohrbaugh, R. H.; Jurs, P. C. Descriptions of Molecular Shape Applied in Studies of Structure/Activity and Structure/Property Relationships. Anal. Chim. Acta 1987, 199, 99-109.
38. Wiener, H. Structural Determination of Paraffin Boiling Points. J. Am. Chem. Soc. 1947, 69, 17-20.
39. Randić, M. On Characterization of Molecular Branching. J. Am. Chem. Soc. 1975, 97, 6609-6615.
40. Stankevich, M. I.; Stankevich, I. V.; Zefirov, N. S. Topological Indices in Organic Chemistry. Russ. Chem. Rev. (Engl. Transl.) 1988, 57, 191-208.
41. Murugan, R.; Grendze, M. P.; Toomey, J. E., Jr.; Katritzky, A. R.; Karelson, M.; Lobanov, V.; Rachwal, P. Predicting Physical Properties from Molecular Structure. CHEMTECH 1994, 24, 17.
42. Karelson, M., Lobanov, V. S.; Katritzky, A. R. Quantum-Chemical Descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96, 1027-1043.
43. Stanton, D. T.; Jurs, P. C. Development and Use of Charged Partial Surface Area Structural Descriptors in Computer-Assisted Quantitative Structure-Property Relationship Studies. Anal. Chem. 1990, 62, 2323-2329.
44. Stanton, D. T.; Egolf, L. M.; Jurs, P. C.; Hicks, M. G. Computer-Assisted Prediction of Normal Boiling Points of Pyrans and Pyrroles. J. Chem. Inf. Comput. Sci. 1992, 32, 306-316.
45. Cramer, R. D. III BC(DEF) Parameters. 1. The Intrinsic Dimensionality of Intermolecular Interactions in the Liquid State. J. Am. Chem. Soc. 1980, 102, 1837-1849.
46. (a) Osmialowski, K.; Halkiewicz, J.; Kaliszan, R. Quantum Chemical Parameters in Correlation Analysis of Gas-Liquid Chromatographic Retention Indices of Amines. J. Chromatogr. 1986, 361, 63-69.
47. (b) Zefirov, N. S.; Kirpichenok, M. A.; Izmailov, F. F.; Trofimov, M. I. Scheme for the Calculation of the Electronegativities of Atoms in a Molecule in the Framework of Sanderson's Principle. Dokl. Akad. Nauk (Engl. Transl.) 1987, 296, 883-887.
48. Rosch, N.; Zerner, M. C. Calculation of Dispersion Energy Shifts in Molecular Electronic Spectra. J. Phys. Chem. 1994, 98, 5817-5823.
49. Amos, A. T.; Burrows, B. L. Solvent-Shift Effects on Electronic Spectra and Excited-State Dipole Moments and Polarizabilities. Adv. Quantum Chem. 1973, 7, 289-313.