Method for fast predicting dissociation constant of hydroxylated polybrominated diphenyl ethers

Abstract

The invention discloses a method for fast predicting the dissociation constant (pKa) of hydroxylated polybrominated diphenyl ethers (HO-PBDEs) and belongs to the technical field of quantitative structure-property relation (QSPR) aiming at chemical environment ecological risk evaluation. The method is characterized in that two molecular structure descriptors including molecular weight Mw and lowestunoccupied molecular orbital energy (ELUMO) representing electron acceptor ability are used to build a QSPR model for predicting the pKa. The method has the advantages that excellent model statisticsperformance is achieved, the square r<2> of a correlation coefficient is 0.90, and root-mean-square error rms is 0.46; simulation external verification and cross verification show that the model is good in robustness and predicting ability; the application domain of the model is represented on the basis of a Williams graph, and the model can be used for predicting the pKa values of 837 HO-PBDEs substituted by different bromine atoms and single hydroxyl and other similar-structured compounds.

Description

technical field [0001] The invention belongs to the technical field of ecological security assessment, in particular to the technical field of quantitative structure-property relationship (QSPR) for environmental ecological risk assessment. Background technique [0002] pK a It is a very important property of organic compounds, which determines the existence form of the compound in the medium, and then determines its solubility, lipophilicity, bioaccumulation and toxicity. Obtain precise pK of organic compounds a Values ​​are of great significance in fields such as environmental chemistry, biochemistry, and medicinal chemistry. As the most basic physical and chemical property parameters of compounds, pK a The experimental data is still quite lacking, and there are problems such as low accuracy, especially for emerging environmental pollutants. Therefore, it is particularly important to develop predictive methods with good performance. [0003] HO-PBDEs are a new class o...

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Problems solved by technology

However, the prediction performance of this series of models is poor, and limited by the selection of training set compounds and application domains, they cannot be used for HO-PBDEs compound pK a calculation

Yu et al. (Yu H Y, Kühne R, Ebert R-U, et al. Prediction of the dissociation constant pK a of organic acids from local molecular parameters of their electronic ground state. J Chem Inf Model,2011,51:2336–2344) calculated three classes of local molecular structure descriptors reflecting the energy and charge information of dissociated functional group atoms using quantum chemical methods , established a QSPR prediction model for 5 types of acids and 7 types of bases. The model has good performance, but it is also limited by the application domain and cannot be applied to HO-PBDEs compounds

In 2015, Yu et al. (Yu H Y, Wondrousch D, Yuan Q, etal.Modeling and predicting pK a values ​​of mono-hydroxylated polychlorinatedbiphenyls(HO-PCBs) and polybrominated diphenyl ethers(HO-PBDEs) by local molecular descriptors.Chemosphere,2015,138:829–836) using similar quantum chemical methods to establish specific HO-PBDEs and hydroxyl pK of polychlorinated biphenyls (HO-PCBs) a Predictive models, however, cannot be conveniently used for such compounds due to the calculations involving complex quantum chemical descriptors and the need for expert experience a prediction, and the model performance also needs to be further improved

It can be seen that the existing models cannot predict the pK of HO-PBDEs and other structurally similar compounds simply and quickly. a value

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