A general linear free energy relationship for predicting partition coefficients of neutral organic compounds

• Published in: Chemosphere (Oxford) Vol. 247; p. 125869
• Main Authors: Chen, Deliang, Wang, Qingyun, Li, Yibao, Li, Yongdong, Zhou, Hui, Fan, Yulan
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.05.2020
• Subjects: Computational chemistry; Hydrogen Bonding; Hydrogen bonding capability; Linear free energy relationship; Linear Models; Models, Chemical; Organic Chemicals - analysis; Organic Chemicals - chemistry; Partition coefficient; Physicochemical property; Quantitative Structure-Activity Relationship; Quantitative structure-property relationship; Solutions; Solvents - analysis; Solvents - chemistry; Water - chemistry; Linear free energy relationship; Computational chemistry; Quantitative structure-property relationship; Partition coefficient; Hydrogen bonding capability; Physicochemical property
• ISSN: 0045-6535; 1879-1298
• DOI: 10.1016/j.chemosphere.2020.125869

Predicting the effects of organic compounds on environments and biological systems is an important objective for environmental chemistry and human health. The logarithm (to base 10) of the n-octanoll–water partition coefficient has been widely used to predict the mentioned properties. However, the suitability of this parameter for the purpose has been questioned, since the environments relating to the properties may be quite different from that of bulk n-octanol. In this study, we used a theoretical derivation approach to develop a model for predicting the partition coefficients of solutes between water and an organic solvent that may be similar to n-octanol or quite different from it. Our model relies on solute descriptors that can be calculated based on solute structures. It was used to predict the n-octanoll–water, hexadecanel–water and chloroforml–water partition coefficients of solutes. The calculated values of the examined parameters agreed well with their experimental counterparts. The model can find application in the accurate prediction of the effects of organic compounds on environments and the physicochemical properties of organic compounds by a full in-silico approach and can provide useful guidance for improving some properties of organic compounds. [Display omitted] •A model is developed for accurately predicting organic solvent-water partition coefficients.•The solute descriptors used in the model are calculated from the structures of the solutes.•This model has potential applications in predicting the properties of organic compounds by a full in silico approach.•This model has potential applications in predicting the effects of organic compounds n environment and human health.•This study can provide useful guidance for improving some properties of organic compounds.