Abstract
Multiple linear regression (MLR) analysis based on a combined use of the modified Xu index and the atom-type based AI indices is performed to construct quantitative structure–property models on several data sets of organic compounds including aliphatic aldehydes and/or ketones. For each of the physical properties (the normal boiling points, molar refractions, gas heat capacities at 25 °C, water solubility at 25 °C, and n-octanol/water partition coefficient at 25 °C ), high quality QSPR models are obtained, particularly the decrease in the standard error is within the range of 23.6–75.9% relative to the linear models with the modified Xu index alone. For individual subsets containing only aldehydes or ketones, in the majority of cases the quality of the model can be further improved. The significant improvement verifies the efficiency of the present approach and also indicates the usefulness of these indices for application to a wide range of physical properties. The results indicate that the physical properties studied are dominated by molecular size but atom types have smaller influences, especially the oxygen atom seems to be most important due to intermolecular polar interactions. The final models are validated to be statistically reliable using the leave-one-out cross-validation and/or an external test set.
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References
Wang, L. and Han, S. (Eds.), Quantitative Structure-Activity Relationships of Organic Compounds (in Chinese), Environmental Scientific Press of China, Beijing, China, 1993.
Kamlet M., Abboud, J.L.M. and Taft R.W., Prog. Phys. Org. Chem., 13 (1981) 485, and references therein.
Hansch, C., Leo, A. and Hoekman, D., Exploring QSAR. Hydrophobic, Electronic and Steric Constants, American Chemical Society, Washington, DC, 1995.
Hansch, C. and Leo, A., Exploring QSAR. Fundamentals and Applications in Chemistry and Biology, American Chemical Society, Washington, DC, 1995.
Xu, L. and Hu, C., Applied Chemical Graph Theory, Scientific Press, Beijing, China, 2000.
Bondi, A., J. Phys. Chem., 68 (1964) 441.
Hermann, R.B., J. Phys. Chem., 76 (1972) 2754.
Amidon, G.L., Yalkowsky, H. and Leung, S.J., J. Pharm. Sci., 63 (1974) 3225.
Stanton, D.T. and Jurs, P.C., Anal. Chem., 62 (1990) 2323.
Grigoras, S., J. Comput. Chem., 11 (1990) 493.
Kortvelyesi, T., Gorgenyi, M. and Heberger, K., Anal. Chim. Acta, 428 (2001) 73.
Reynolds, W.F., Prog. Phys. Org. Chem., 14 (1983) 165.
Franke, R., Theoretical Drug Design Methods, Elsevier, Amsterdam, The Netherlands, 1984.
Nelson, T.M. and Jurs, P.C., J. Chem. Inf. Comput. Sci., 34 (1994) 601.
Dixon, S.L. and Jurs, P.C., J. Comput. Chem., 13 (1992) 492.
Grunenberg, J. and Herges, R., J. Chem. Inf. Comput. Sci., 35 (1995) 905.
Taft, R.W., J. Prog. Phys. Org. Chem., 14 (1983) 247.
Kier, L.B. and Hall, L.H., Molecular Connectivity in Chemistry and Drug Research, Academic Press, New York, 1976.
Kier, L.B. and Hall, L.H., Molecular Connectivity in Structure-Activity Studies, Research Studies Press, Letchworth, UK, 1986.
Hosoya, H., Bull. Chem. Soc. Jpn., 44 (1971) 2332.
Balaban, A.T., Chem. Phys. Lett., 89 (1982) 399.
Bonchev, D. and Trinajstić, N., J. Chem. Phys., 67 (1977) 4517.
Schultz, H.P., J. Chem. Inf. Comput. Sci., 29 (1989) 227.
Wiener, H., J. Am. Chem. Soc., 69 (1947) 17.
Ren, B., J. Chem. Inf. Comput. Sci., 39 (1999) 139.
Ren, B., Chen, G. and Xu, Y., Acta Chim. Sinica, 57 (1999) 563 (in Chinese).
Trinajstić, N., Chemical Graph Theory, 2nd ed., CRC Press, Boca Raton, FL, 1992.
Hall, L.H., Mohney, B. and Kier, L.B., J. Chem. Inf. Comput. Sci., 31 (1991) 76.
Maw, H.H. and Hall, L.H., J. Chem. Inf. Comput. Sci., 41 (2001) 1248.
Rose, K., Hall, L.H. and Kier, L.B., J. Chem. Inf. Comput. Sci., 42 (2002) 651.
Ren, B., Comput. Chem., 26 (2002) 1121.
Ren, B., Comput. Chem., 26 (2002) 357.
Ren, B., J. Mol. Struct. (THEOCHEM), 586 (2002) 137.
Ren, B., J. Chem. Inf. Comput. Sci., 42 (2002) 858.
Ren, B., J. Chem. Inf. Comput. Sci., 43 (2003) 161.
Ren, B., J. Chem. Inf. Comput. Sci., 43 (2003) 1121.
Ren, B., Chemometrics Intel. Lab. Sys., 66 (2003) 29.
Weast, R., CRC Handbook of Chemistry and Physics, 70th ed., CRC Press, Boca Raton, FL, 1989-1990.
Lide, D.R. and Milne, G.W.A., Handbook of Data on Common Organic Compounds, CRC Press, Boca Raton, FL, 1992.
Dictionary of Organic Chemistry. 6th ed.; Chapman & Hall, London, 1996.
Dean, J.A., Lange's Handbook of Chemistry, 15th Ed., McGraw-Hill, Beijing, China, 1999.
Yaws, C.L., Chemical Properties Handbook, McGraw-Hill, Beijing, China, 1999.
Huang, F. and Liu, X., Aldehydes In Encyclopedia of Chemical Industry, Vol. 13. Chemical Industry Press, Beijing, China, 1997 (in Chinese).
Huang, F. and Liu, X., Ketones, In Encyclopedia of Chemical Industry, Vol. 16. Chemical Industry Press, Beijing, China, 1997 (in Chinese).
Wessel, M.D. and Jurs P.C., J. Chem. Inf. Comput. Sci., 35 (1995) 841.
Xu, L., Chemometrical Method (in Chinese), Scientific Press of China, Beijing, China, 1996.
Needham, D.E., Wei, I.-C. and Seybold, P.G., J. Am. Chem. Soc., 110 (1988) 4186.
Mihalić, Z. and Trinajstić, N. J. Chem. Educ., 69 (1992) 701.
Lin, Z., Xu, J., Liu, S., Zhen, X. and Li, Z., Acta Phys.-Chim. Sinica (in Chinese), 16 (2000) 153.
Reid, R.C., Prausnitz, J.M. and Poling, B.E., The Properties of Gases and Liquids, 4th ed., McGraw-Hill, New York, 1987.
Nelson, T.M. and Jurs, P.C., J. Chem. Inf. Comput. Sci., 34(1994) 601.
Klopman, G., Li, J.-Y., Wang, S. and Dimayuga, M., J. Chem. Inf. Comput. Sci., 34(1994) 752.
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Ren, B. New atom-type-based AI topological indices: Application to QSPR studies of aldehydes and ketones. J Comput Aided Mol Des 17, 607–619 (2003). https://doi.org/10.1023/B:JCAM.0000005764.26206.74
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DOI: https://doi.org/10.1023/B:JCAM.0000005764.26206.74