Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction.
Daniela Rodrigues SilvaJoyce K DaréMatheus P FreitasPublished in: Beilstein journal of organic chemistry (2020)
Molecular polarity governs lipophilicity, which in turn determines important agrochemical and environmental properties, such as soil sorption and bioconcentration of organic compounds. Since the C-F bond is the most polar in organic chemistry, the orientation of fluorine substituents originating from the rotation around C-C(F) bonds should affect the polarity and, consequently, the physicochemical and biological properties of fluorine-containing agrochemicals. Accordingly, this study aims to determine the most likely conformers of some fluorine-containing agrochemicals and to correlate their molecular dipole moments with the respective n-octanol/water partition coefficients (log P), in order to investigate the dependence of the lipophilicity with the molecular conformation.