Conformational Preferences of Fluorine-Containing Agrochemicals and their Implications for Lipophilicity Prediction

  1. Daniela R Silva,
  2. Joyce K Daré and
  3. Matheus P FreitasORCID Logo

Submitting author affiliation: Federal University of Lavras, Lavras, Brazil

Beilstein Arch. 2020, 202066. doi:10.3762/bxiv.2020.66.v1

Published 02 Jun 2020

  • Preprint

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 originated 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 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.

Keywords: dipole moment; fluorinated compounds; gauche effect; herbicides; log P

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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Silva, D. R.; Daré, J. K.; Freitas, M. P. Beilstein Arch. 2020, 202066. doi:10.3762/bxiv.2020.66.v1

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