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Photolysis of insecticide methomyl in various solvents: An experimental and theoretical study

Authorized Users Only
2020
Authors
Tomašević, Anđelka
Mijin, Dušan
Radišić, Marina
Prlainović, Nevena
Cvijetić, Ilija
Kovačević, Danijela
Marinković, Aleksandar
Article (Published version)
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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 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 method
Source:
Journal of Photochemistry and Photobiology A-Chemistry, 2020, 391
Publisher:
  • 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
[ Google Scholar ]
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1
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4480
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - 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 . .

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