Design of New Alkylphenols with Theoretical Values of their Water/ Octanol Partition Coefficients

Abstract

In our previous work, we established a predictive QSPR (Quantitative Structure-Property Relationship) model for the water/octanol partition coefficient, based on electronic energy (ET), LUMO (Lowest Unoccupied Molecular Orbital) energy, and the energy gap (ΔEgap). This model has been shown to be suitable for predicting properties of new alkylphenols falling within its applicability domain, with a 5% risk level. The present study, which builds upon that earlier work, aims to expand the database for this family of compounds by designing new alkylphenols that fit within the established model's applicability domain and by predicting their water/octanol partition coefficients. In this context, we designed a series of forty-two (42) new alkylphenols. All these molecules were optimized at the B3LYP/6-311G(d,p) level of theory, and vibrational frequencies were calculated at the same level. Water/octanol partition coefficients calculated for these molecules using the model indicate that they are all lipophilic. The formation reaction for these new compounds proceeds spontaneously, accompanied by heat release and a decrease in disorder.