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Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction.

ABSTRACT: 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.

SUBMITTER: Silva DR

PROVIDER: S-EPMC7554678 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction.

Silva Daniela Rodrigues DR Daré Joyce K JK Freitas Matheus P MP

Beilstein journal of organic chemistry 20201005

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 det ...[more]

PMID: 33093926

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