Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study
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2020
Authors
Tomašević, AnđelkaMijin, Dušan
Radišić, Marina
Prlainović, Nevena
Cvijetić, Ilija
Kovačević, Danijela
Marinković, Aleksandar
Article (Published version)
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This study describes photolysis of 1 x 10(-4) M methomyl solution in deionized water and in eleven organic solvents, both polar and nonpolar: methanol, ethanol, n-propanol, isopropanol, sec-butanol, tert-butanol, isobutanol, isopentanol, n-hexane, acetonitrile, and dichloromethane. Photolysis of methomyl at 254 nm was performed using Osram mercury lamp (6 x 8 W) by exposing to irradiation for five hours. All photolytic methomyl reactions were studied by UV/Vis spectroscopy within a wavelength range of 190 - 300 nm (Spectrum Mode), and at 233.4 nm (Quantitative Mode), while the rate of photodecomposition of methomyl was measured using UV spectroscopy and HPLC. In order to get better insight in the photolysis of methomyl, a liquid chromatography-mass spectrometry (LC-MSn) was used. The rate of methomyl photolysis was solvent-specific and the following reaction rate order was established: deionized water gt tert-butanol gt n-hexane gt sec-butanol gt ethanol gt isopentanol gt i...sobutanol gt isopropanol gt methanol gt acetonitrile gt dichloromethane gt n-propanol. Both nonspecific and specific solvent-solute interactions contribute mutually to the differences in the obtained quantum yields. Results of quantum chemical calculations, using CBS-QB3 method, provided insights into the solvent effects on both ground and excited state. The LC/MSn analysis showed the formation of several photolytic products.
Keywords:
Solvent effect / Quantum yields / Dielectric constant / Acceptor and donor numbers / LFER / CBS-QB3 methodSource:
Journal of Photochemistry and Photobiology A-Chemistry, 2020, 391Publisher:
- Elsevier Science Sa, Lausanne
Funding / projects:
- Development of integrated management of harmful organisms in plant production in order to overcome resistance and to improve food quality and safety (RS-46008)
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1016/j.jphotochem.2020.112366
ISSN: 1010-6030
WoS: 000514008000021
Scopus: 2-s2.0-85077930720
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Tomašević, Anđelka AU - Mijin, Dušan AU - Radišić, Marina AU - Prlainović, Nevena AU - Cvijetić, Ilija AU - Kovačević, Danijela AU - Marinković, Aleksandar PY - 2020 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4480 AB - This study describes photolysis of 1 x 10(-4) M methomyl solution in deionized water and in eleven organic solvents, both polar and nonpolar: methanol, ethanol, n-propanol, isopropanol, sec-butanol, tert-butanol, isobutanol, isopentanol, n-hexane, acetonitrile, and dichloromethane. Photolysis of methomyl at 254 nm was performed using Osram mercury lamp (6 x 8 W) by exposing to irradiation for five hours. All photolytic methomyl reactions were studied by UV/Vis spectroscopy within a wavelength range of 190 - 300 nm (Spectrum Mode), and at 233.4 nm (Quantitative Mode), while the rate of photodecomposition of methomyl was measured using UV spectroscopy and HPLC. In order to get better insight in the photolysis of methomyl, a liquid chromatography-mass spectrometry (LC-MSn) was used. The rate of methomyl photolysis was solvent-specific and the following reaction rate order was established: deionized water gt tert-butanol gt n-hexane gt sec-butanol gt ethanol gt isopentanol gt isobutanol gt isopropanol gt methanol gt acetonitrile gt dichloromethane gt n-propanol. Both nonspecific and specific solvent-solute interactions contribute mutually to the differences in the obtained quantum yields. Results of quantum chemical calculations, using CBS-QB3 method, provided insights into the solvent effects on both ground and excited state. The LC/MSn analysis showed the formation of several photolytic products. PB - Elsevier Science Sa, Lausanne T2 - Journal of Photochemistry and Photobiology A-Chemistry T1 - Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study VL - 391 DO - 10.1016/j.jphotochem.2020.112366 ER -
@article{ author = "Tomašević, Anđelka and Mijin, Dušan and Radišić, Marina and Prlainović, Nevena and Cvijetić, Ilija and Kovačević, Danijela and Marinković, Aleksandar", year = "2020", abstract = "This study describes photolysis of 1 x 10(-4) M methomyl solution in deionized water and in eleven organic solvents, both polar and nonpolar: methanol, ethanol, n-propanol, isopropanol, sec-butanol, tert-butanol, isobutanol, isopentanol, n-hexane, acetonitrile, and dichloromethane. Photolysis of methomyl at 254 nm was performed using Osram mercury lamp (6 x 8 W) by exposing to irradiation for five hours. All photolytic methomyl reactions were studied by UV/Vis spectroscopy within a wavelength range of 190 - 300 nm (Spectrum Mode), and at 233.4 nm (Quantitative Mode), while the rate of photodecomposition of methomyl was measured using UV spectroscopy and HPLC. In order to get better insight in the photolysis of methomyl, a liquid chromatography-mass spectrometry (LC-MSn) was used. The rate of methomyl photolysis was solvent-specific and the following reaction rate order was established: deionized water gt tert-butanol gt n-hexane gt sec-butanol gt ethanol gt isopentanol gt isobutanol gt isopropanol gt methanol gt acetonitrile gt dichloromethane gt n-propanol. Both nonspecific and specific solvent-solute interactions contribute mutually to the differences in the obtained quantum yields. Results of quantum chemical calculations, using CBS-QB3 method, provided insights into the solvent effects on both ground and excited state. The LC/MSn analysis showed the formation of several photolytic products.", publisher = "Elsevier Science Sa, Lausanne", journal = "Journal of Photochemistry and Photobiology A-Chemistry", title = "Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study", volume = "391", doi = "10.1016/j.jphotochem.2020.112366" }
Tomašević, A., Mijin, D., Radišić, M., Prlainović, N., Cvijetić, I., Kovačević, D.,& Marinković, A.. (2020). Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study. in Journal of Photochemistry and Photobiology A-Chemistry Elsevier Science Sa, Lausanne., 391. https://doi.org/10.1016/j.jphotochem.2020.112366
Tomašević A, Mijin D, Radišić M, Prlainović N, Cvijetić I, Kovačević D, Marinković A. Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study. in Journal of Photochemistry and Photobiology A-Chemistry. 2020;391. doi:10.1016/j.jphotochem.2020.112366 .
Tomašević, Anđelka, Mijin, Dušan, Radišić, Marina, Prlainović, Nevena, Cvijetić, Ilija, Kovačević, Danijela, Marinković, Aleksandar, "Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study" in Journal of Photochemistry and Photobiology A-Chemistry, 391 (2020), https://doi.org/10.1016/j.jphotochem.2020.112366 . .