QSPR treatment of the unified nonspecific solvent polarity scale

Journal of Chemical Information and Computer Sciences

Volumn 37, Issue 4, 1997, Pages 756-761

  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: 0001124698     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci970011k     Document Type: Article

References (40)

1. Kirkwood, J. G. Theory of Solutions of Molecules Containing Widely Separated Charges with Special Application to Zwitterions. J. Chem. Phys. 1934, 2, 351-361.
2. Onsager, L. Electric Moments of Molecules in Liquids. J. Am. Chem. Soc. 1936, 58, 1486-1493.
3. Kirkwood, J. G. The Dielectric Polarization of Polar Liquids. J. Chem. Phys. 1939, 7, 911-919.
4. Block, H.; Walker, S. M. A Modification of the Onsager Theory for a Dielectric. Chem. Phys. Lett. 1973, 19, 363-364.
5. Brady, J. E.; Carr, P. W. An Analysis of Dielectric Models of Solvatochromism. J. Phys. Chem. 1985, 89, 5759-5766.
6. Drago, R. S. A Unified Scale for Understanding and Predicting Non-specific Solvent Polarity: A Dynamic Cavity Model. J. Chem. Soc. Perkin Trans. 2 1992, 1827-1838.
7. Abboud, J. L.; Kamlet, M. J.; Taft, R. W. Regarding a Generalized Scale of Solvent Polarities. J. Am. Chem. Soc. 1977, 99, 8325-8327.
8. Kamlet, M. J.; Abbound J.-L. M.; Abraham M. H.; Taft, R. W. Linear Solvation Energy Relationships. 23. A Comprehensive Collection of the Solvatochromic Parameters, π*, α, and β, and Some Methods for Simplifying the Generalized Solvatochromic Equation J. Org. Chem. 1983, 48, 2877-2887.
9. Kamlet, M. J.; Abboud, J. L. M.; Taft, R. W. An Examination of Linear Solvation Energy Relationships. Prog. Phys. Org. Chem. 1981, 13, 485-623.
10. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH Publishers: Weinheim, 1988.
11. Reichardt, C. Solvatochromic Dyes as Solvent Polarity Indicators. Chem. Rev. 1994, 94, 2319-2358.
12. Abraham, M. H. Scales of Solute Hydrogen-bonding: Their Construction and Application to Physicochemical and Biochemical Processes. Chem. Soc. Rev. 1993, 22, 73-83.
13. Drago, R. S. Applications of Electrostatic-Covalent Models in Chemistry; Surfside Scientific Publishers: Gainesville, FL, 1994.
14. Lowrey, A. H.; Cramer, C. J.; Urban, J. J.; Famini, G. R. Quantum Chemical Descriptors for Linear Solvation Energy Relationships. Computers Chem. 1995, 19, 209-215.
15. (a)Famini, G. R.; Ashman, W. P.; Mickiewicz, A. P; Wilson, L. Y. Using Theoretical Descriptors in Quantitative Structure-Activity Relationships: Opiate Receptor Activity by Fentanyl-like Compounds. Quant. Struct.-Act. Relat. 1992, 11, 162-170.
16. (b)Donovan, W. H.; Famini, G. R. Using Theoretical Descriptors in Structure Activity Relationships: Retention Indices of Sulfur Vesicants and Related Compounds. J Chem. Soc., Perkin Trans. 2 1996, 83-89.
17. Cramer, C. J.; Famini, G. R.; Lowrey, A. H. Use of Calculated Quantum Chemical Properties as Surrogates for Solvatochromic Parameters in Structure-Activity Relationships. Acc. Chem. Res. 1993, 26, 599-605.
18. Trinajstic, N. Chemical Graph Theory, 2nd ed.; CRC Press: Boca Raton, FL, 1992.
19. Famini, G. R.; Wilson, L. Y. Using Theoretical Descriptors in Quantitative Structure-Property Relationships: 3-Carboxybenzisoxazole Decarboxylation Kinetics. J. Chem. Soc., Perkin Trans. 2 1994, 1641-1650.
20. 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, 17-23.
21. Katritzky, A. R.; Mu, L.; Lobanov, V. S.; Karelson, M. Correlation of Boiling Points with Molecular Structure. I. A Training Set of 298 Diverse Organics and a Test Set of 9 Simple Inorganics. J. Phys. Chem. 1996, 100, 10400-10407.
22. Katritzky, A. R.; Maran, U.; Karelson, M.; Lobanov, V. S. Prediction of Melting Points for the Substituted Benzenes: A QSPR Approach manuscript in preparation.
23. Katritzky, A. R.; Lobanov, V. S.; Karelson, M.; Murugan, R; Grendze, M. J.; Toomey, J. E., Jr. Comprehensive Descriptors for Structural and Statistical Analysis. 1. Correlations Between Structure and Physical Properties of Substituted Pyridines. Rev. Roum. Chim. 1996, 41, 851-867.
24. Katritzky, A. R.; Mu, L.; Karelson, M. A QSPR Study of the Solubility of Gases and Vapors in Water. J. Chem. Inf. Comput. Sci, 1996, 36, 1162-1168.
25. Katritzky, A. R.; Ignatchenko, E. S.; Barcock, R. A.; Lobanov, V. S.; Karelson, M. Prediction of Gas Chromatographic Retention Times and Response Factors Using a General Quantitative Structure-Property Relationship Treatment. Anal. Chem. 1994, 66, 1799-1807.
26. Katritzky, A. R.; Rachwal, P.; Law, K. W.; Karelson M; Lobanov, V. S. Prediction of Polymer Glass Transition Temperatures Using a General Quantitative Structure-Property Relationship Treatment. J. Chem. Inf. Comput. Sci. 1996, 36, 879-884.
27. Huibers, P. D. T.; Lobanov, V. S.; Katritzky, A. R.; Shah, D. O.; Karelson, M. Prediction of Critical Micelle Concentration Using a Quantitative Structure-Property Relationship Approach. 1. Nonionic Surfactants. Langmuir 1996, 12, 1462-1470.
28. Bustamante, P.; Drago, R. S. Extension of the Unified Solvation Model to Systems Requiring a Cavity Term. J. Chem. Soc., Perkin Trans. 2 Submitted for publication.
29. George, J. E.; Drago, R. S. Extension of the Unified Solvation Model to Organometallic and Polycyclic Aromatic Probes. Inorg. Chem. 1996, 35, 239-241.
30. PCMODEL, Manual, 5th ed.; Serena Software: Bloomington, IN, 1992.
31. 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.
32. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. CODESSA, Training Manual; Gainesville, FL, 1995.
33. 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.
34. Wiener, H. Structural Determination of Paraffin Boiling Points. J. Am. Chem. Soc. 1947, 69, 17-20.
35. Randić, M. On Characterization of Molecular Branching. J. Am. Chem. Soc. 1975, 97, 6609-6615.
36. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis; John Wiley & Sons Inc.: New York, 1986.
37. Stankevich, M. I.; Stankevich, I. V.; Zefirov, N. S. Topological Indices in Organic Chemistry. Russ. Chem. Rev. (Engl. Transl.) 1988, 57, 191-208.
38. Karelson, M.; Lobanov, V. S.; Katritzky, A. R. Quantum-Chemical Descriptors in QSAR/QSPR Studies. Chem. Rev. 1996, 96, 1027-1043.
39. 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.
40. 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.