Chlorophenols, QSAR

Three-dimensional quantitative structure activity relationship (3D-QSAR) analysis for in vitro toxicity of chlorophenols to HepG2 cells Y. Liu, J.N. Chen, J.S. Zhao, H.X. Yu, X.D. Wang, J. Jiang, H.J. Jin, J.F. Zhang and L.S. Wang... 

Van Gestel, C.A.M. and Ma, W.-C. Development of QSAR s in soil ecotoxicology earthworm toxicity and soil sorption of chlorophenols, chlorobenzenes and chloroanilines. Water, Air, SoilPollut, 69(3-4) 265-276, 1993. 

Halogenated phenols correlate well with Hammett s constant (a). Figure 6.24 shows the linear trend of the c values of 3-chlorophenol, 4-chlorophenol, 3,4-dichlorophenol, and 3,5-dichlorophenol with respect to their first-order reaction rate constants. Aromatic compounds with substituents in the meta and para positions have pronounced steric differences and result in a well-defined trend. Table 6.9 summarizes all the QSAR models discussed above. 

Kaiser, K.L.E., Dixon, D.G., Hodson, P.V. (1984) QSAR studies on chlorophenols, chlorobenzenes and para-substituted phenols. In QSAR in Environmental Toxicology. Kaiser, K.L.E., Ed., pp. 189-206, D. Reidel Publ. Co., Dordrecht, The Netherlands. 

Konemann, W.H., Musch, A. (1981) Quantitative structure-activity relationships in fish toxicity studies. Part 2 The influence of pH on the QSAR of chlorophenols. Toxicology 19, 223-228. 

Kaiser, K.L.E., Dixon, D.G., Hodson, PV. (1984) QSAR studies on chlorophenols, chlorobenzenes and para-substituted phenols. In QSAR in Environmental Toxicology. Kaiser, K. L. E., Ed., pp. 189-206, D. Reidel Publishing Co., Dordrecht, The Netherlands. Kamlet, M.J., Doherty, R.M., Carr, P.W., Mackay, D., Abraham, M.H., Taft, R.W. (1988) Linear solvation energy relationship. 44. Parameter estimation rules that allow accurate prediction of octanol/water partition coefficients and other solubility and toxicity properties of polychlorinated biphenyls and polycyclic aromatic hydrocarbons. Environ. Sci. Technol. 22, 503-509. Kanazawa, J. (1981) Measurement of the bioconcentration factors of pesticides by fresh-water fish and their correlation with physicochemical properties of acute toxicities. Pest. Sci. 12, 417-424. 

Another QSAR involving correction for ionization was developed by van Gestel et al. (1991 1993). Their 1991 paper reported the following correlation for a series of chlorobenzenes, chlo-rophenols, and chloroanilines, in which the log Kow values of the chlorophenols were corrected for ionization ... 

Ravanel, P., Taillander, G., Tissut, M. and Benoit-Guyod, J.L. (1985). Effects of Chlorophenols on Isolated Plant Mitochondria Activities A QSAR Study. Ecotox.Environ.Safe., 9,300-320. 

Todeschini, R., Bettiol, C., Giurin, G., Gramatica, P, Miana, P. and Argese, E. (1996a). Modeling and Prediction by Using WHIM Descriptors in QSAR Studies. Submitochondrial Particles (SMP) as Toxicity Biosensors of Chlorophenols. Chemosphere, 33,71-79. 

Modeling and prediction by using WHIM descriptors in QSAR studies submitochondrial partides (SMP) as toxicity biosensors of chlorophenols. Chemosphere, 33, 71-79. 

The structure descriptors are not intercorrelated to allow the recognition of the significant variables. If, for example, activity data on a set of chlorophenols are investigated with respect to their log and values, a statistically significant QSAR may be obtained with either one of the descriptors, but an assignment of the relevant descriptor is not feasible, because those are linearly intercorrelated. 

Devillers, J. and Chambon, P. (1986) Toxicity and QSAR of chlorophenols on Daphnia magna. Bull Environ. Contam. Toxicol, 37, 599-605. 

Gestel, C. A. M. van, Ma, W. and Smit, C. E. (1991) Development of QSARs in terrestrial ecotoxicology earthworm toxicity and soil sorption of chlorophenols, chlorobenzenes and dichloroaniline. ScL Total Environ, 109/110, 589-604. 

QSAR, acute toxicity, chlorinated organic compounds, structure-toxicity relationships, surface area descriptors, Fujita-Ban anaylsis, chlorobenzenes, chlorophenols. 

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