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Cronin, M. T. D.; Bowers, G. S.; Sinks, G. D.; Schultz, T. W.
SAR and QSAR in environmental research, 01/2000, Letnik: 11, Številka: 3-4Journal Article
QSARs based upon the logarithm of the octanol-water partition coefficient, logP, and energy of the lowest unoccupied molecular orbital, E LUMO were developed to model the toxicity of aliphatic compounds to the marine bacterium Vibrio fischeri. Statistically robust, hydrophobic-dependent QSARs were found for chloroalcohols and haloacetonitriles. Modelling of the toxicity of the haloesters and the diones required the use of terms to describe both hydrophobicity and electrophilicity. The differences in intercepts, slopes, and fit of these models suggest different electrophilic mechanisms occur between classes, as well as within the diones and haloesters. In order to model globally the toxicity of aliphatic compounds to V. fischeri, all the data determined in this study were combined with those determined previously for alkanones, alkanals, and alkenals. A highly predictive two-parameter QSAR pT 15 = 0.760(log P) −0.625(E LUMO ) −0.466; n = 63, s = 0.462, r 2 = 0.846, F = 171, Pr > F = 0.0001 was developed for the combined data that models across classes and is independent of mechanisms of action. The toxicity of these compounds to V. fischeri compares well to the toxicity (50% population growth inhibition) to the ciliate Tetrahymena pyriformis (r 2 = 0.850).
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