Prediction of rate constants for radical degradation of aromatic pollutants in water matrix: a QSAR study

Abstract

We present the results of the QSAR/QSPR study on the degradation rate constants of 78 aromatic compounds by the hydroxyl radicals in water. A genetic algorithm and multiple regression analysis were applied to select the descriptors and to generate the correlation models. Additionally to DRAGON descriptors, the parameters from quantum-chemical calculations at semiempirical and at density functional theory level (B3LYP/6-31G(d,p)) were applied. The most predictive model is a four-variable model that had a good ratio of the number of variables and the predictive ability to avoid overfitting. As it was expected, the main contribution to the degradation rate was given by the E(HOMO) parameter. Additionally, a number of topological descriptors in selected models showed an importance of polarizability term regarding the degradation rate of compounds. Overall, the applied GA-MLRA approach with the use of quantum-chemical and DRAGON generated descriptors showed good results in this study. The obtained statistically robust structure-degradation rate model can be used for future studies of the presence of organic compounds in the environment, and especially their degradation by hydroxyl radicals as a part of a water/wastewater treatment.