Prediction of Henry's Law Constants by a Quantitative Structure Property Relationship and Neural Networks

Journal of Chemical Information and Computer Sciences

Volumn 41, Issue 3-6, 2001, Pages 1150-1161

  English, Niall J ^a   Carroll, Daniel G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIP (QSPR);

COMPUTER SIMULATION; ERROR ANALYSIS; HYDROGEN BONDS; REGRESSION ANALYSIS;

NEURAL NETWORKS;

EID: 0035470305     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci010361d     Document Type: Article

References (44)

1. Sander, R. Experimental HLC Database (Version 3); Air Chemistry Department, Max Planck Institute: P.O. Box 3060, 55020 Mainz, Germany, 1999.
2. Meylan, W. M. Experimental HLC Database, Syracuse Research Corporation: 1999.
3. Hine, J.; Mookerjee P. K. Intrinsic Hydrophilic Character of Organic Compounds - Correlations in Terms of Structural Contributions. J. Org. Chem. 1975, 40(3), 292-298.
4. Cabani, S.; Gianni, P.; Mollica, V.; Lepori, L. Group Contributions to the Thermodynamic Properties of Non-Ionic Organic Solutes in Dilute Aqueous Solution. J. Solution Chem. 1981, 10(8), 563-595.
5. Nirmalakhandan, N. N.; Speece, R. E. QSAR Model for Predicting Henry's Constant. Environ. Sci. Technol. 1988, 22, 1349-1357.
6. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure - Activity Analysis; Research Studies: Hertfordshire, Great Britain, 1986.
7. Meylan, W. M.; Howard, P. H. Bond Contribution Method for Estimating Henry's Law Constants. Environ. Tox. Chem. 1991, 10, 1283-1293.
8. 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.
9. Stuper, A. J.; Brugger, W. E.; Jurs, P. C. Computer Assisted Studies of Chemical Structure and Biological Function; Wiley-Interscience: New York, 1979.
10. Suzuki, T.; Ohtaguchi, K.; Koide, K. Application of Principal Components-Analysis to Calculate Henry's Constants from Molecular-Structure. Computers Chem. 1992, 16(1), 41-52.
11. 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 298K, and a New Method for its Determination. J. Chem. Soc., Perkin Trans. 2 1994, 1777-1791.
12. Nirmalakhandan, N. N.; Brennan, R. A.; Speece, R. E. Predicting Henry's Law Constant and the Effect of Temperature on Henry's Law Constant. Water Res. 1997, 31(6), 1471-1481.
13. Hawker, D. W. Vapour-Pressures and Henry's Law Constants of Polychlorinated-Biphenyls. Environ. Sci. Technol. 1989, 23(10), 1250-1253.
14. Sabljic, A.; Gusten, H. Predicting Henry's Law Constants for Polychlorinated-Biphenyls. Chemosphere 1989, 19(10/11), 1503-1511.
15. Brunner, S.; Hornung, E.; Santl, H.; Wolff, E.; Piringer O. G.; Altschuh, J.; Bruggemann, R. Henry's Law Constants for Polychlorinated-Biphenyls - Experimental Determination and Structure Property Relationships. Environ. Sci. Technol. 1990, 24(11), 1751-1754.
16. Dunnivant, F. M.; Elzerman A. W.; Jurs P. C.; Hasan, M. N. Quantitative Structure Property Relationships for Aqueous Solubilities and Henry's Law Constants of Polychlorinated-Biphenyls. Environ. Sci. Technol. 1992, 26(8), 1567-1573.
17. Chiu, R. M. H.; Chen, B. D. Correlation of the Henry's Law Constant for Non-Polar Liquids in Molten Polyisobutylene. Ind. Eng. Chem. Res. 1996, 35, 4386-4388.
18. Quale, O. R. The Parachors of Organic Compounds. Chem. Rev. 1953, 53, 439-589.
19. Reid, R. C.; Prausnitz, J. M.; Poling, B. E. The Properties of Gases and Liquids, 4th ed.; McGraw-Hill: New York, 1987; Appendix A.
20. Abraham, M. H.; McGowan, J. C. The Use of Characteristic Volumes to Measure Cavity Terms in Reversed Phase Liquid-Chromatography. Chromatographia 1987, 23(4), 243-246.
21. Miller, K. J., Savchik, J. A. New Empirical-Method to Calculate Average Molecular Polarizabilities. J. Am. Chem. Soc. 1979, 101(24), 7206-7213.
22. Baudet, J.; Guy, J.; Tillieu, J., Calcul des Susceptibilités Magnétiques Principales de la Molécule de Benzène. J. Phys. Radium 1960, 21, 600-608.
23. Abraham, M. H.; Greiller, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. Hydrogen Bonding. 7. A Scale of Solute Hydrogen-Bond Acidity Based on LogK-values for Complexation in Tetrachloromethane. J. Chem. Soc., Perkins Trans. 2 1989, 699-711.
24. Abraham, M. H.; Greiller, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. Hydrogen-Bonding. 10. A Scale of Solute Hydrogen-Bond Basicity Using LogK-values for Complexation in Tetrachloromethane. J. Chem. Soc., Perkins Trans. 2 1990, 521-529.
25. Wiener, H. Structural Determination of Paraffin Boiling Points. J. Am. Chem. Soc. 1947, 69, 17-20.
26. Randic, M. On Molecular Identification Numbers. J. Chem. Inf. Comput. Sci. 1984, 24, 164-175.
27. 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(21), 2323-2329.
28. Gasteiger, J.; Marsili, M. Iterative Partial Equalization of Orbital Electronegativity - A Rapid Access to Atomic Charges. Tetrahedron 1980, 36, 3219-3288.
29. Bondi, A. van der Waals Volumes and Radii. J. Phys. Chem. 1964, 68(3), 441-451.
30. Mackay, D.; Shiu, W. Y. A Critical Review of Henry's Law Constants for Chemicals of Environmental Interest. J. Phys. Chem. Ref. Data 1981, 10(4), 1175-1199.
31. Abraham, M. H.; Fuchs, R.; Whiting, G. S.; Chambers, E. C. Thermodynamics of Solute Transfer from Water to Hexadecane. J. Chem. Soc., Perkin Trans. 2 1990, 291-300.
32. Abraham, M. H. J. Chem. Soc., Faraday Trans, 1 1984 , 80, 153-181.
33. Abraham, M. H.; Matteoli, E. Thermodynamics of Solution of Homologous Series of Solutes in Water. J. Chem. Soc., Faraday Trans. 1 1988, 84, 1985-2000.
34. Wilhelm, E.; Battino, R.; Wilcock, R. J. Low-Pressure Solubility of Gases in Liquid Water. Chem. Rev. 1977, 77, 219-262.
35. Bagno, A.; Lucchini, V.; Scorrano, G. Thermodynamics of Protonation of Ketones and Esters and Energies of Hydration of their Conjugate Acids. J. Phys. Chem. 1991, 95, 345-352.
36. Gibbs, P. R.; Radzicka, A.; Wolfenden, R. The Anomalous Hydrophilic Character of Proline. J. Am. Chem. Soc. 1991, 113, 4714-4715.
37. Press, W. H.; Flannery, B. P.; Teukolsky, S. A.; Vetterling W. T. Numerical Recipes, 2nd ed.; Cambridge University Press: 1992.
38. Myers, R. H. Classical and Modern Regression Analysis with Applications, 2nd ed.: Duxbury, 1990.
39. SPSS Inc., Recognition Systems Inc. Neural Connection 2.0 User's/ Applications Guide; SPSS Software Inc.: Chicago, IL, U.S.A., 1997.
40. Topliss, J. G.; Edwards, R. P. Chance Factors in Studies of Quantitative Structure - Activity-Relationships. J. Med. Chem. 1979, 22(10), 1238-1244.
41. (41 ) Furnival, G. M.; Wilson, R. W., Jr. Regression by Leaps and Bounds. Technometrics 1974, 16(4), 499-511.
42. Visual Numerics Inc. IMSL (R) Fortran 90 MP Library, Version 3.0; Houston, TX, U.S.A., 1998.
43. Belsley, D. A.; Kuh, E.; Welsh, R. E. Regression Diagnostics: Identifying Influential Data and Sources of Collineariry; Wiley: New York, 1980.
44. Brennan, R. A.; Nirmalakhandan, N. N.; Speece, R. E. Comparison of Predictive Methods for Henry's Law Coefficients of Organic Compounds. Water Res. 1998, 32(6), 1901-1911.