QSAR models for the ozonation of diverse volatile organic compounds at different temperatures

Abstract

In order to assess the fate and persistence of volatile organic compounds (VOCs) in the atmosphere, it is necessary to determine their oxidation rate constants for their reaction with ozone (k_O3). However, given that experimental values of k_O3 are only available for a few hundred compounds and their determination is expensive and time-consuming, developing predictive models for k_O3 is of great importance. Thus, this study aimed to develop reliable quantitative structure–activity relationship (QSAR) models for 302 values of 149 VOCs across a broad temperature range (178–409 K). The model was constructed based on the combination of a simplified molecular-input line-entry system (SMILES) and temperature as an experimental condition, namely quasi-SMILES. In this study, temperature was incorporated in the models as an independent feature. The hybrid optimal descriptor generated from the combination of quasi-SMILES and HFG (hydrogen-filled graph) was used to develop reliable, accurate, and predictive QSAR models employing the CORAL software. The balance between the correlation method and four different target functions (target function without considering IIC or CII, target function using each IIC or CII, and target function based on the combination of IIC and CII) was used to improve the predictability of the QSAR models. The performance of the developed models based on different target functions was compared. The correlation intensity index (CII) significantly enhanced the predictability of the model. The best model was selected based on the numerical value of R_m² of the calibration set (split #1, R_train² = 0.9834, R_calibration² = 0.9276, R_validation² = 0.9136, and calibration = 0.8770). The promoters of increase/decrease for log k_O3 were also computed based on the best model. The presence of a double bond (BOND10000000 and $10 000 000 000), absence of halogen (HALO00000000), and the nearest neighbor codes for carbon equal to 321 (NNC-C⋯321) are some significant promoters of endpoint increase.