Density functional theory calculation of lipophilicity for organophosphate type pesticides

Filip Ž. Vlahović; Saša Ivanović; Matija Zlatar; Maja Gruden

doi:10.2298/JSC170725104V

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Published: Dec 30, 2017

DOI: https://doi.org/10.2298/JSC170725104V

Keywords:

DFT lipophilicity organophosphate pesticides toxicity partition coefficient

Filip Ž. Vlahović

University of Belgrade, Innovation center of the Faculty of Chemistry, Studentski trg 12-16, 11000 Belgrade

Saša Ivanović

University of Belgrade, Faculty of Veterinary Medicine, Department of Pharmacology and Toxicology, Bulevar oslobodjenja 18, 11000 Belgrade

Matija Zlatar

University of Belgrade, Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoseva 12, 11000 Belgrade

Maja Gruden

University of Belgrade-Faculty of Chemistry

http://orcid.org/0000-0002-0746-5754

Abstract

Density functional method with continuum solvation model is used for calculation of partition coefficient log K_OW and determination of lipophilicity of 22 most frequently used organophosphate type pesticides. Excellent agreement with experimental data is obtained using three different density functional approximations (one local, one general gradient and one hybrid), and our result highlights DFT as a reliable and trustworthy method for calculation and of lipophilicity for this important class of molecules. Furthermore, calculated lipophilicity results are associated with experimentally determined LD₅₀ and LC₅₀ values, showing that the most toxic pesticides are these with transient characteristics (medium lipophilicity), although this concussion must be taken with a caution due to the many factors influencing the ingestion and action of a certain substance in the body beside lipophilicity.

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[1]

F. Ž. Vlahović, S. Ivanović, M. Zlatar, and M. Gruden, “Density functional theory calculation of lipophilicity for organophosphate type pesticides”, J. Serb. Chem. Soc., vol. 82, no. 12, pp. 1369–1378, Dec. 2017.

Issue

Vol. 82 No. 12 (2017)

Section

Theoretical Chemistry

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

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