Computational insights into E/Z isomerism of fluoxastrobin, an antifungal agent: A DFT/TD-DFT study

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dc.contributor.authorSerin, Sumeyya
dc.date.accessioned2024-08-04T20:53:41Z
dc.date.available2024-08-04T20:53:41Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractHerein, inspired by the success of strobilurins in fungicidal activity bioassays, DFT (Density Functional Theory) -based quantum chemical computations were performed on fluoxastrobin, a fluorinated strobilurin fungicide. Its formulation has E/Z isomerism around the C=N bond. It is highly advantageous to utilize quantum chemical methods to acquire more insights into E/Z isomerism and to gain supplemental confirmations in terms of experimental results. In this respect, the geometries of the E and Z isomers of fluoxastrobin were optimized both in the vacuum and in 1-octanol, acetonitrile, DMSO, and water phases using the DFT/B3LYP/6-311++G (d, p) methodology. Both experimental and theoretical FTIR and UV-vis evaluations were performed for the isomers. TD-DFT/B3LYP/6-311++G (d, p) theory level computations were determined that the observed peaks were mostly caused from the pi ->pi* and n ->pi* transitions. Also, quantum chemical reactivity descriptors and physi-cochemical parameters were calculated for both vacuum and solvent phases. Accordingly, computations in all studied phases estimate the E isomer to be preferred with energy values in the range of 2.51-3.77 kcal/mol. Natural bond orbital (NBO) analysis was also carried out to determine the intermolecular interactions and their corresponding stabilization energies. Last, with the help of Gibbs solvation free energy values, 1-octanol/water partition coefficients were calculated and lipophilicity evaluations of both isomers were performed.en_US
dc.identifier.doi10.1016/j.molstruc.2023.135713
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85156199915en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2023.135713
dc.identifier.urihttps://hdl.handle.net/11616/101332
dc.identifier.volume1287en_US
dc.identifier.wosWOS:001002851400001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectStrobilurinen_US
dc.subjectDFTen_US
dc.subjectEen_US
dc.subjectZ isomeren_US
dc.subjectSolvent effecten_US
dc.subjectNBOen_US
dc.titleComputational insights into E/Z isomerism of fluoxastrobin, an antifungal agent: A DFT/TD-DFT studyen_US
dc.typeArticleen_US

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