Milošević, Milena D.

Link to this page

Authority KeyName Variants
ca796d35-d1cb-436a-8e26-d9bd732cc5ea
  • Milošević, Milena D. (9)
  • Milošević, Milena (1)
Projects
Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200135 (University of Belgrade, Faculty of Technology and Metallurgy)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200288 (Innovation Center of the Faculty of Chemistry)
Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids The part of the bilateral project between Serbia and Montenegro titled “Synthesis of Schiff bases and investigation of their antimicrobial and antioxidant activity.”
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200105 (University of Belgrade, Faculty of Mechanical Engineering) Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200116 (University of Belgrade, Faculty of Agriculture)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry) Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200325 (Military Technical Institute - MTI, Belgrade)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200326 (University of Defence, Military Academy, Belgrade)

Author's Bibliography

Lignin based microspheres for effective dyes removal: Design, synthesis and adsorption mechanism supported with theoretical study

Rabab, Salih; Veličković, Zlate; Milošević, Milena; Pavlović, Vera P.; Cvijetić, Ilija; Sofrenić, Ivana V.; Gržetić, Jelena D.; Marinković, Aleksandar

(Academic Press, 2023)

TY  - JOUR
AU  - Rabab, Salih
AU  - Veličković, Zlate
AU  - Milošević, Milena
AU  - Pavlović, Vera P.
AU  - Cvijetić, Ilija
AU  - Sofrenić, Ivana V.
AU  - Gržetić, Jelena D.
AU  - Marinković, Aleksandar
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6018
AB  - Multifunctional lignin bio-based adsorbent, b-LMS, was obtained via inverse copolymerization in the suspension of acryloyl modified kraft lignin (KfL-AA) and bio-based trimethylolpropane triacrylate (bio-TMPTA). Morphological and structural characterization of KfL-AA and b-LMS was performed using BET, FTIR, Raman, NMR, TGA, SEM, and XPS techniques. The b-LMS microspheres with 253 ± 42 μm diameters, 69.4 m2 g−1 surface area, and 59% porosity efficiently adsorb Malachite Green (MG), Tartrazine (T), and Methyl Red (MR) dye. The influence of pH, pollutant concentration, temperature, and time on the removal efficiency was studied in a batch mode. Favorable and spontaneous processes with high adsorption capacities e.g. 116.8 mg g−1 for MG, 86.8 mg g−1 for T, and 68.6 mg g−1 for MR indicate the significant adsorptive potential of b-LMS. Results from diffusional and single mass transfer resistance studies indicate that pore diffusion is a rate-limiting step. Theoretical calculations confirmed a higher affinity of b-LMS to cationic dye MG compared with an anionic and neutral one, i.e. T and MR, respectively. The data fitting from a flow system, using semi-empirical equations and Pore Surface Diffusion Modelling (PSDM) provided breakthrough point determination. The results from the desorption and competitive adsorption study proved the exceptional performance of b-LMS. Moreover, sulfation of b-LMS, i.e.production of b-LMS-OSO3H, introduced high-affinity sulfate groups with respect to cationic dye and cations. Developed methodology implements the principle of sustainable development and offers concept whose results contribute to the minimization of environmental pollution.
PB  - Academic Press
T2  - Journal of Environmental Management
T1  - Lignin based microspheres for effective dyes removal: Design, synthesis and adsorption mechanism supported with theoretical study
VL  - 326
SP  - 116838
DO  - 10.1016/j.jenvman.2022.116838
ER  - 
@article{
author = "Rabab, Salih and Veličković, Zlate and Milošević, Milena and Pavlović, Vera P. and Cvijetić, Ilija and Sofrenić, Ivana V. and Gržetić, Jelena D. and Marinković, Aleksandar",
year = "2023",
abstract = "Multifunctional lignin bio-based adsorbent, b-LMS, was obtained via inverse copolymerization in the suspension of acryloyl modified kraft lignin (KfL-AA) and bio-based trimethylolpropane triacrylate (bio-TMPTA). Morphological and structural characterization of KfL-AA and b-LMS was performed using BET, FTIR, Raman, NMR, TGA, SEM, and XPS techniques. The b-LMS microspheres with 253 ± 42 μm diameters, 69.4 m2 g−1 surface area, and 59% porosity efficiently adsorb Malachite Green (MG), Tartrazine (T), and Methyl Red (MR) dye. The influence of pH, pollutant concentration, temperature, and time on the removal efficiency was studied in a batch mode. Favorable and spontaneous processes with high adsorption capacities e.g. 116.8 mg g−1 for MG, 86.8 mg g−1 for T, and 68.6 mg g−1 for MR indicate the significant adsorptive potential of b-LMS. Results from diffusional and single mass transfer resistance studies indicate that pore diffusion is a rate-limiting step. Theoretical calculations confirmed a higher affinity of b-LMS to cationic dye MG compared with an anionic and neutral one, i.e. T and MR, respectively. The data fitting from a flow system, using semi-empirical equations and Pore Surface Diffusion Modelling (PSDM) provided breakthrough point determination. The results from the desorption and competitive adsorption study proved the exceptional performance of b-LMS. Moreover, sulfation of b-LMS, i.e.production of b-LMS-OSO3H, introduced high-affinity sulfate groups with respect to cationic dye and cations. Developed methodology implements the principle of sustainable development and offers concept whose results contribute to the minimization of environmental pollution.",
publisher = "Academic Press",
journal = "Journal of Environmental Management",
title = "Lignin based microspheres for effective dyes removal: Design, synthesis and adsorption mechanism supported with theoretical study",
volume = "326",
pages = "116838",
doi = "10.1016/j.jenvman.2022.116838"
}
Rabab, S., Veličković, Z., Milošević, M., Pavlović, V. P., Cvijetić, I., Sofrenić, I. V., Gržetić, J. D.,& Marinković, A.. (2023). Lignin based microspheres for effective dyes removal: Design, synthesis and adsorption mechanism supported with theoretical study. in Journal of Environmental Management
Academic Press., 326, 116838.
https://doi.org/10.1016/j.jenvman.2022.116838
Rabab S, Veličković Z, Milošević M, Pavlović VP, Cvijetić I, Sofrenić IV, Gržetić JD, Marinković A. Lignin based microspheres for effective dyes removal: Design, synthesis and adsorption mechanism supported with theoretical study. in Journal of Environmental Management. 2023;326:116838.
doi:10.1016/j.jenvman.2022.116838 .
Rabab, Salih, Veličković, Zlate, Milošević, Milena, Pavlović, Vera P., Cvijetić, Ilija, Sofrenić, Ivana V., Gržetić, Jelena D., Marinković, Aleksandar, "Lignin based microspheres for effective dyes removal: Design, synthesis and adsorption mechanism supported with theoretical study" in Journal of Environmental Management, 326 (2023):116838,
https://doi.org/10.1016/j.jenvman.2022.116838 . .
17
14
12

Bio-membrane based on modified cellulose, lignin, and tannic acid for cation and oxyanion removal: Experimental and theoretical study

Perendija, Jovana; Veličković, Zlate S.; Cvijetić, Ilija; Lević, Steva M.; Marinković, Aleksandar; Milošević, Milena D.; Onjia, Antonije

(Elsevier, 2021)

TY  - JOUR
AU  - Perendija, Jovana
AU  - Veličković, Zlate S.
AU  - Cvijetić, Ilija
AU  - Lević, Steva M.
AU  - Marinković, Aleksandar
AU  - Milošević, Milena D.
AU  - Onjia, Antonije
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4770
AB  - Two optimized methods, based on epoxy-amino reactivity of the Cellulose fibres (Cell) modified with diethylenetriamine (Cell‒DETA), (3-Glycidyloxypropyl)trimethoxysilane (Cell-Glymo), Lignin modified with epichlorohydrine (EL) and Tannic acid (TA), as an additional crosslinker, were developed for the production of the bio-renewable Cell-EL and Cell-EL-TA membranes. The influences of pH, contact time, adsorbent dose, and temperature on adsorption performances were studied by batch adsorption tests. The calculated capacities: 53.9, 99.9, 97.8 and 63.5, 115.8, 127.5 mg g−1 for Ni2+, Pb2+, Cr(VI) using Cell-EL and Cell-EL-TA, respectively, were obtained from Langmuir model fitting at 25 °C. The thermodynamic parameters indicated spontaneous and low endothermic processes. The results of the kinetic study, i.e. pseudo-second-order (PSO) and Weber-Morris (W-M), suggest an intra-particle diffusion as a rate-limiting step. The semi-empirical quantum chemical calculations aided the analysis of the non-specific and specific adsorbent/adsorbate interactions and their contribution to the overall bonding mechanism. Membrane utility was confirmed by performing a bed column study. In general, three main environmental issues of the present study, biodegradability of the used membrane, desorption efficiency, and development of the technology for the effective effluent water treatment and safe disposal of by-products highly conform to the demand of integrated environmental management system applicability in practice.
PB  - Elsevier
T2  - Process Safety and Environmental Protection
T1  - Bio-membrane based on modified cellulose, lignin, and tannic acid for cation and oxyanion removal: Experimental and theoretical study
VL  - 147
SP  - 609
EP  - 625
DO  - 10.1016/j.psep.2020.12.027
ER  - 
@article{
author = "Perendija, Jovana and Veličković, Zlate S. and Cvijetić, Ilija and Lević, Steva M. and Marinković, Aleksandar and Milošević, Milena D. and Onjia, Antonije",
year = "2021",
abstract = "Two optimized methods, based on epoxy-amino reactivity of the Cellulose fibres (Cell) modified with diethylenetriamine (Cell‒DETA), (3-Glycidyloxypropyl)trimethoxysilane (Cell-Glymo), Lignin modified with epichlorohydrine (EL) and Tannic acid (TA), as an additional crosslinker, were developed for the production of the bio-renewable Cell-EL and Cell-EL-TA membranes. The influences of pH, contact time, adsorbent dose, and temperature on adsorption performances were studied by batch adsorption tests. The calculated capacities: 53.9, 99.9, 97.8 and 63.5, 115.8, 127.5 mg g−1 for Ni2+, Pb2+, Cr(VI) using Cell-EL and Cell-EL-TA, respectively, were obtained from Langmuir model fitting at 25 °C. The thermodynamic parameters indicated spontaneous and low endothermic processes. The results of the kinetic study, i.e. pseudo-second-order (PSO) and Weber-Morris (W-M), suggest an intra-particle diffusion as a rate-limiting step. The semi-empirical quantum chemical calculations aided the analysis of the non-specific and specific adsorbent/adsorbate interactions and their contribution to the overall bonding mechanism. Membrane utility was confirmed by performing a bed column study. In general, three main environmental issues of the present study, biodegradability of the used membrane, desorption efficiency, and development of the technology for the effective effluent water treatment and safe disposal of by-products highly conform to the demand of integrated environmental management system applicability in practice.",
publisher = "Elsevier",
journal = "Process Safety and Environmental Protection",
title = "Bio-membrane based on modified cellulose, lignin, and tannic acid for cation and oxyanion removal: Experimental and theoretical study",
volume = "147",
pages = "609-625",
doi = "10.1016/j.psep.2020.12.027"
}
Perendija, J., Veličković, Z. S., Cvijetić, I., Lević, S. M., Marinković, A., Milošević, M. D.,& Onjia, A.. (2021). Bio-membrane based on modified cellulose, lignin, and tannic acid for cation and oxyanion removal: Experimental and theoretical study. in Process Safety and Environmental Protection
Elsevier., 147, 609-625.
https://doi.org/10.1016/j.psep.2020.12.027
Perendija J, Veličković ZS, Cvijetić I, Lević SM, Marinković A, Milošević MD, Onjia A. Bio-membrane based on modified cellulose, lignin, and tannic acid for cation and oxyanion removal: Experimental and theoretical study. in Process Safety and Environmental Protection. 2021;147:609-625.
doi:10.1016/j.psep.2020.12.027 .
Perendija, Jovana, Veličković, Zlate S., Cvijetić, Ilija, Lević, Steva M., Marinković, Aleksandar, Milošević, Milena D., Onjia, Antonije, "Bio-membrane based on modified cellulose, lignin, and tannic acid for cation and oxyanion removal: Experimental and theoretical study" in Process Safety and Environmental Protection, 147 (2021):609-625,
https://doi.org/10.1016/j.psep.2020.12.027 . .
16
3
15
13

Supplementary data for the article: Perendija, J.; Veličković, Z. S.; Cvijetić, I.; Lević, S.; Marinković, A. D.; Milošević, M.; Onjia, A. Bio-Membrane Based on Modified Cellulose, Lignin, and Tannic Acid for Cation and Oxyanion Removal: Experimental and Theoretical Study. Process Safety and Environmental Protection 2021, 147, 609–625. https://doi.org/10.1016/j.psep.2020.12.027.

Perendija, Jovana; Veličković, Zlate S.; Cvijetić, Ilija; Lević, Steva M.; Marinković, Aleksandar; Milošević, Milena D.; Onjia, Antonije

(Institution of Chemical Engineers, 2021)

TY  - DATA
AU  - Perendija, Jovana
AU  - Veličković, Zlate S.
AU  - Cvijetić, Ilija
AU  - Lević, Steva M.
AU  - Marinković, Aleksandar
AU  - Milošević, Milena D.
AU  - Onjia, Antonije
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4771
PB  - Institution of Chemical Engineers
PB  - Elsevier
T2  - Process Safety and Environmental Protection
T1  - Supplementary data for the article: Perendija, J.; Veličković, Z. S.; Cvijetić, I.; Lević, S.; Marinković, A. D.; Milošević, M.; Onjia, A. Bio-Membrane Based on Modified Cellulose, Lignin, and Tannic Acid for Cation and Oxyanion Removal: Experimental and Theoretical Study. Process Safety and Environmental Protection 2021, 147, 609–625. https://doi.org/10.1016/j.psep.2020.12.027.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4771
ER  - 
@misc{
author = "Perendija, Jovana and Veličković, Zlate S. and Cvijetić, Ilija and Lević, Steva M. and Marinković, Aleksandar and Milošević, Milena D. and Onjia, Antonije",
year = "2021",
publisher = "Institution of Chemical Engineers, Elsevier",
journal = "Process Safety and Environmental Protection",
title = "Supplementary data for the article: Perendija, J.; Veličković, Z. S.; Cvijetić, I.; Lević, S.; Marinković, A. D.; Milošević, M.; Onjia, A. Bio-Membrane Based on Modified Cellulose, Lignin, and Tannic Acid for Cation and Oxyanion Removal: Experimental and Theoretical Study. Process Safety and Environmental Protection 2021, 147, 609–625. https://doi.org/10.1016/j.psep.2020.12.027.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4771"
}
Perendija, J., Veličković, Z. S., Cvijetić, I., Lević, S. M., Marinković, A., Milošević, M. D.,& Onjia, A.. (2021). Supplementary data for the article: Perendija, J.; Veličković, Z. S.; Cvijetić, I.; Lević, S.; Marinković, A. D.; Milošević, M.; Onjia, A. Bio-Membrane Based on Modified Cellulose, Lignin, and Tannic Acid for Cation and Oxyanion Removal: Experimental and Theoretical Study. Process Safety and Environmental Protection 2021, 147, 609–625. https://doi.org/10.1016/j.psep.2020.12.027.. in Process Safety and Environmental Protection
Institution of Chemical Engineers..
https://hdl.handle.net/21.15107/rcub_cherry_4771
Perendija J, Veličković ZS, Cvijetić I, Lević SM, Marinković A, Milošević MD, Onjia A. Supplementary data for the article: Perendija, J.; Veličković, Z. S.; Cvijetić, I.; Lević, S.; Marinković, A. D.; Milošević, M.; Onjia, A. Bio-Membrane Based on Modified Cellulose, Lignin, and Tannic Acid for Cation and Oxyanion Removal: Experimental and Theoretical Study. Process Safety and Environmental Protection 2021, 147, 609–625. https://doi.org/10.1016/j.psep.2020.12.027.. in Process Safety and Environmental Protection. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_4771 .
Perendija, Jovana, Veličković, Zlate S., Cvijetić, Ilija, Lević, Steva M., Marinković, Aleksandar, Milošević, Milena D., Onjia, Antonije, "Supplementary data for the article: Perendija, J.; Veličković, Z. S.; Cvijetić, I.; Lević, S.; Marinković, A. D.; Milošević, M.; Onjia, A. Bio-Membrane Based on Modified Cellulose, Lignin, and Tannic Acid for Cation and Oxyanion Removal: Experimental and Theoretical Study. Process Safety and Environmental Protection 2021, 147, 609–625. https://doi.org/10.1016/j.psep.2020.12.027." in Process Safety and Environmental Protection (2021),
https://hdl.handle.net/21.15107/rcub_cherry_4771 .

Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents

Milošević, Milena D.; Marinković, Aleksandar; Petrović, Predrag; Klaus, Anita; Nikolić, Milica G.; Prlainović, Nevena Ž.; Cvijetić, Ilija

(Elsevier, 2020)

TY  - JOUR
AU  - Milošević, Milena D.
AU  - Marinković, Aleksandar
AU  - Petrović, Predrag
AU  - Klaus, Anita
AU  - Nikolić, Milica G.
AU  - Prlainović, Nevena Ž.
AU  - Cvijetić, Ilija
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4254
AB  - In this study we synthesized a series of sixteen bis(imino)pyridines (BIPs) starting from 2,6-diaminopyridine and various aromatic aldehydes, and evaluated their antioxidant, antibacterial, antifungal and acetylcholinesterase (AChE) inhibitory activity. The chemical structures were elucidated by FTIR, elemental analysis, ESR and HRMS. 1 H and 13C NMR spectra couldn’t be acquired due to the formation of stable, carbon-centered radical cations in a solution, as confirmed by ESR spectroscopy and DFT calculations. The in vitro antioxidant potency was evaluated using four assays: free radical scavenging activity (DPPH and ABTS), reducing power and total antioxidant capacity assay. BIPs demonstrated excellent antioxidant properties, and two derivatives proved to be more potent than reference antioxidants (ascorbic acid and Trolox) in all assays. DFT calculations on ωB97XD/6- 311++g(d,p) level of theory provided valuable insights into the radical scavenging mechanism of BIPs. For hydroxyl-substituted BIPs, hydrogen atom transfer (HAT) is a predominant mechanism, while the single electron transfer coupled with proton transfer (SET-PT) governs the antioxidant activity of other derivatives. Intramolecular hydrogen bonding (IHB) plays an important role in the mechanism of antioxidant activity as revealed by noncovalent interaction analysis and rotational barrier calculations. The spin density of radical cations is localized on carbon atoms of a pyridine ring, which corroborates with g-factors and multiplicity obtained from ESR analysis. The most potent BIP exhibited moderate inhibitory activity toward AChE (IC50 = 20 ± 4 μM), while molecular docking suggested binding at the peripheral anionic site of AChE with the MMFF94 binding enthalpy of −43.4 kcal/mol. Moderate in vitro antimicrobial activity of BIPs have been determined against several pathogenic bacterial strains: Pseudomonas aeruginosa, Escherichia coli, Enterococcus faecalis, Staphylococcus aureus and clinical isolate of methicillin resistant S. aureus (MRSA). The antifungal activity of BIPs toward Candida albicans was also confirmed. The similarity ensemble approach combined with molecular docking suggested leucyl aminopeptidase as the probable antimicrobial target for the three most potent BIP derivatives.
PB  - Elsevier
T2  - Bioorganic Chemistry
T1  - Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents
VL  - 102
DO  - 10.1016/j.bioorg.2020.104073
ER  - 
@article{
author = "Milošević, Milena D. and Marinković, Aleksandar and Petrović, Predrag and Klaus, Anita and Nikolić, Milica G. and Prlainović, Nevena Ž. and Cvijetić, Ilija",
year = "2020",
abstract = "In this study we synthesized a series of sixteen bis(imino)pyridines (BIPs) starting from 2,6-diaminopyridine and various aromatic aldehydes, and evaluated their antioxidant, antibacterial, antifungal and acetylcholinesterase (AChE) inhibitory activity. The chemical structures were elucidated by FTIR, elemental analysis, ESR and HRMS. 1 H and 13C NMR spectra couldn’t be acquired due to the formation of stable, carbon-centered radical cations in a solution, as confirmed by ESR spectroscopy and DFT calculations. The in vitro antioxidant potency was evaluated using four assays: free radical scavenging activity (DPPH and ABTS), reducing power and total antioxidant capacity assay. BIPs demonstrated excellent antioxidant properties, and two derivatives proved to be more potent than reference antioxidants (ascorbic acid and Trolox) in all assays. DFT calculations on ωB97XD/6- 311++g(d,p) level of theory provided valuable insights into the radical scavenging mechanism of BIPs. For hydroxyl-substituted BIPs, hydrogen atom transfer (HAT) is a predominant mechanism, while the single electron transfer coupled with proton transfer (SET-PT) governs the antioxidant activity of other derivatives. Intramolecular hydrogen bonding (IHB) plays an important role in the mechanism of antioxidant activity as revealed by noncovalent interaction analysis and rotational barrier calculations. The spin density of radical cations is localized on carbon atoms of a pyridine ring, which corroborates with g-factors and multiplicity obtained from ESR analysis. The most potent BIP exhibited moderate inhibitory activity toward AChE (IC50 = 20 ± 4 μM), while molecular docking suggested binding at the peripheral anionic site of AChE with the MMFF94 binding enthalpy of −43.4 kcal/mol. Moderate in vitro antimicrobial activity of BIPs have been determined against several pathogenic bacterial strains: Pseudomonas aeruginosa, Escherichia coli, Enterococcus faecalis, Staphylococcus aureus and clinical isolate of methicillin resistant S. aureus (MRSA). The antifungal activity of BIPs toward Candida albicans was also confirmed. The similarity ensemble approach combined with molecular docking suggested leucyl aminopeptidase as the probable antimicrobial target for the three most potent BIP derivatives.",
publisher = "Elsevier",
journal = "Bioorganic Chemistry",
title = "Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents",
volume = "102",
doi = "10.1016/j.bioorg.2020.104073"
}
Milošević, M. D., Marinković, A., Petrović, P., Klaus, A., Nikolić, M. G., Prlainović, N. Ž.,& Cvijetić, I.. (2020). Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents. in Bioorganic Chemistry
Elsevier., 102.
https://doi.org/10.1016/j.bioorg.2020.104073
Milošević MD, Marinković A, Petrović P, Klaus A, Nikolić MG, Prlainović NŽ, Cvijetić I. Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents. in Bioorganic Chemistry. 2020;102.
doi:10.1016/j.bioorg.2020.104073 .
Milošević, Milena D., Marinković, Aleksandar, Petrović, Predrag, Klaus, Anita, Nikolić, Milica G., Prlainović, Nevena Ž., Cvijetić, Ilija, "Synthesis, characterization and SAR studies of bis(imino)pyridines as antioxidants, acetylcholinesterase inhibitors and antimicrobial agents" in Bioorganic Chemistry, 102 (2020),
https://doi.org/10.1016/j.bioorg.2020.104073 . .
1
19
3
17
15

Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study

Assaleh, Mohamed H.; Božić, Aleksandra R.; Bjelogrlić, Snežana K.; Milošević, Milena D.; Simić, Milena R.; Marinković, Aleksandar; Cvijetić, Ilija

(2019)

TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana K.
AU  - Milošević, Milena D.
AU  - Simić, Milena R.
AU  - Marinković, Aleksandar
AU  - Cvijetić, Ilija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3846
AB  - Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH∙). The appearance of thiolic –SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.
T2  - Structural Chemistry
T1  - Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study
VL  - 30
IS  - 6
SP  - 2447
EP  - 2457
DO  - 10.1007/s11224-019-01371-4
ER  - 
@article{
author = "Assaleh, Mohamed H. and Božić, Aleksandra R. and Bjelogrlić, Snežana K. and Milošević, Milena D. and Simić, Milena R. and Marinković, Aleksandar and Cvijetić, Ilija",
year = "2019",
abstract = "Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH∙). The appearance of thiolic –SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.",
journal = "Structural Chemistry",
title = "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study",
volume = "30",
number = "6",
pages = "2447-2457",
doi = "10.1007/s11224-019-01371-4"
}
Assaleh, M. H., Božić, A. R., Bjelogrlić, S. K., Milošević, M. D., Simić, M. R., Marinković, A.,& Cvijetić, I.. (2019). Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry, 30(6), 2447-2457.
https://doi.org/10.1007/s11224-019-01371-4
Assaleh MH, Božić AR, Bjelogrlić SK, Milošević MD, Simić MR, Marinković A, Cvijetić I. Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry. 2019;30(6):2447-2457.
doi:10.1007/s11224-019-01371-4 .
Assaleh, Mohamed H., Božić, Aleksandra R., Bjelogrlić, Snežana K., Milošević, Milena D., Simić, Milena R., Marinković, Aleksandar, Cvijetić, Ilija, "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study" in Structural Chemistry, 30, no. 6 (2019):2447-2457,
https://doi.org/10.1007/s11224-019-01371-4 . .
10
3
10
8

Supplementary data for the article: Assaleh, M. H.; Božić, A. R.; Bjelogrlić, S.; Milošević, M.; Simić, M.; Marinković, A. D.; Cvijetić, I. N. Water-Induced Isomerism of Salicylaldehyde and 2-Acetylpyridine Mono- and Bis-(Thiocarbohydrazones) Improves the Antioxidant Activity: Spectroscopic and DFT Study. Struct Chem 2019, 30 (6), 2447–2457. https://doi.org/10.1007/s11224-019-01371-4

Assaleh, Mohamed H.; Božić, Aleksandra R.; Bjelogrlić, Snežana K.; Milošević, Milena D.; Simić, Milena R.; Marinković, Aleksandar; Cvijetić, Ilija

(2019)

TY  - DATA
AU  - Assaleh, Mohamed H.
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana K.
AU  - Milošević, Milena D.
AU  - Simić, Milena R.
AU  - Marinković, Aleksandar
AU  - Cvijetić, Ilija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3848
T2  - Structural Chemistry
T1  - Supplementary data for the article: Assaleh, M. H.; Božić, A. R.; Bjelogrlić, S.; Milošević, M.; Simić, M.; Marinković, A. D.; Cvijetić, I. N. Water-Induced Isomerism of Salicylaldehyde and 2-Acetylpyridine Mono- and Bis-(Thiocarbohydrazones) Improves the Antioxidant Activity: Spectroscopic and DFT Study. Struct Chem 2019, 30 (6), 2447–2457. https://doi.org/10.1007/s11224-019-01371-4
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3848
ER  - 
@misc{
author = "Assaleh, Mohamed H. and Božić, Aleksandra R. and Bjelogrlić, Snežana K. and Milošević, Milena D. and Simić, Milena R. and Marinković, Aleksandar and Cvijetić, Ilija",
year = "2019",
journal = "Structural Chemistry",
title = "Supplementary data for the article: Assaleh, M. H.; Božić, A. R.; Bjelogrlić, S.; Milošević, M.; Simić, M.; Marinković, A. D.; Cvijetić, I. N. Water-Induced Isomerism of Salicylaldehyde and 2-Acetylpyridine Mono- and Bis-(Thiocarbohydrazones) Improves the Antioxidant Activity: Spectroscopic and DFT Study. Struct Chem 2019, 30 (6), 2447–2457. https://doi.org/10.1007/s11224-019-01371-4",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3848"
}
Assaleh, M. H., Božić, A. R., Bjelogrlić, S. K., Milošević, M. D., Simić, M. R., Marinković, A.,& Cvijetić, I.. (2019). Supplementary data for the article: Assaleh, M. H.; Božić, A. R.; Bjelogrlić, S.; Milošević, M.; Simić, M.; Marinković, A. D.; Cvijetić, I. N. Water-Induced Isomerism of Salicylaldehyde and 2-Acetylpyridine Mono- and Bis-(Thiocarbohydrazones) Improves the Antioxidant Activity: Spectroscopic and DFT Study. Struct Chem 2019, 30 (6), 2447–2457. https://doi.org/10.1007/s11224-019-01371-4. in Structural Chemistry.
https://hdl.handle.net/21.15107/rcub_cherry_3848
Assaleh MH, Božić AR, Bjelogrlić SK, Milošević MD, Simić MR, Marinković A, Cvijetić I. Supplementary data for the article: Assaleh, M. H.; Božić, A. R.; Bjelogrlić, S.; Milošević, M.; Simić, M.; Marinković, A. D.; Cvijetić, I. N. Water-Induced Isomerism of Salicylaldehyde and 2-Acetylpyridine Mono- and Bis-(Thiocarbohydrazones) Improves the Antioxidant Activity: Spectroscopic and DFT Study. Struct Chem 2019, 30 (6), 2447–2457. https://doi.org/10.1007/s11224-019-01371-4. in Structural Chemistry. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3848 .
Assaleh, Mohamed H., Božić, Aleksandra R., Bjelogrlić, Snežana K., Milošević, Milena D., Simić, Milena R., Marinković, Aleksandar, Cvijetić, Ilija, "Supplementary data for the article: Assaleh, M. H.; Božić, A. R.; Bjelogrlić, S.; Milošević, M.; Simić, M.; Marinković, A. D.; Cvijetić, I. N. Water-Induced Isomerism of Salicylaldehyde and 2-Acetylpyridine Mono- and Bis-(Thiocarbohydrazones) Improves the Antioxidant Activity: Spectroscopic and DFT Study. Struct Chem 2019, 30 (6), 2447–2457. https://doi.org/10.1007/s11224-019-01371-4" in Structural Chemistry (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3848 .

Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5

Milošević, Milena D.; Prlainović, Nevena Z.; Milčić, Miloš K.; Nikolić, Vesna; Božić, Aleksandra R.; Bigović, Miljan; Marinković, Aleksandar

(Springer, New York, 2018)

TY  - DATA
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Milčić, Miloš K.
AU  - Nikolić, Vesna
AU  - Božić, Aleksandra R.
AU  - Bigović, Miljan
AU  - Marinković, Aleksandar
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3255
PB  - Springer, New York
T2  - Journal of the Iranian Chemical Society
T1  - Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3255
ER  - 
@misc{
author = "Milošević, Milena D. and Prlainović, Nevena Z. and Milčić, Miloš K. and Nikolić, Vesna and Božić, Aleksandra R. and Bigović, Miljan and Marinković, Aleksandar",
year = "2018",
publisher = "Springer, New York",
journal = "Journal of the Iranian Chemical Society",
title = "Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3255"
}
Milošević, M. D., Prlainović, N. Z., Milčić, M. K., Nikolić, V., Božić, A. R., Bigović, M.,& Marinković, A.. (2018). Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5. in Journal of the Iranian Chemical Society
Springer, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3255
Milošević MD, Prlainović NZ, Milčić MK, Nikolić V, Božić AR, Bigović M, Marinković A. Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5. in Journal of the Iranian Chemical Society. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3255 .
Milošević, Milena D., Prlainović, Nevena Z., Milčić, Miloš K., Nikolić, Vesna, Božić, Aleksandra R., Bigović, Miljan, Marinković, Aleksandar, "Supplementary material for the article: Milošević, M. D.; Prlainović, N. Ž.; Milčić, M.; Nikolić, V.; Božić, A.; Bigović, M.; Marinković, A. D. Solvent, Structural, Quantum Chemical Study and Antioxidative Activity of Symmetrical 1-Methyl-2,6-Bis[2-(Substituted Phenyl)Ethenyl]Pyridinium Iodides. Journal of the Iranian Chemical Society 2018, 15 (11), 2483–2501. https://doi.org/10.1007/s13738-018-1437-5" in Journal of the Iranian Chemical Society (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3255 .

Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides

Milošević, Milena D.; Prlainović, Nevena Z.; Milčić, Miloš K.; Nikolić, Vesna; Božić, Aleksandra R.; Bigović, Miljan; Marinković, Aleksandar

(Springer, New York, 2018)

TY  - JOUR
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Milčić, Miloš K.
AU  - Nikolić, Vesna
AU  - Božić, Aleksandra R.
AU  - Bigović, Miljan
AU  - Marinković, Aleksandar
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2216
AB  - 15 symmetric 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides were synthesized in this work. Their structures were characterized using IR, H-1 and C-13 NMR, and UV-Vis spectroscopy. DFT calculations indicated that s-trans/s-trans conformation prevail in all compounds. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear solvation-free energy relationships (LSER), i.e., Kamlet-Taft and Catalan models. A linear free energy relationship (LFER) in the form of single substituent parameter equations (SSP) was used to postulate quantitative structure-property relations of substituent effect on NMR data. TD-DFT results showed dependence of electronic transition on the substituent effects. The push-pull character of these compounds was analyzed by differences in C-13 chemical shift of the ethylenic double bond in 2- and 6-positions of cross-conjugated with pyridinum central ring. Also, the quotient of the occupations for the bonding pi and anti-bonding pi* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with pi*/pi and C-13 chemical shift differences of the bridging group proved them to be adequate descriptor of push-pull character. Synthesized compounds were screened for the antioxidant activity, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical methods, and results demonstrated moderate antioxidant potential.
PB  - Springer, New York
T2  - Journal of the Iranian Chemical Society
T1  - Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides
VL  - 15
IS  - 11
SP  - 2483
EP  - 2501
DO  - 10.1007/s13738-018-1437-5
ER  - 
@article{
author = "Milošević, Milena D. and Prlainović, Nevena Z. and Milčić, Miloš K. and Nikolić, Vesna and Božić, Aleksandra R. and Bigović, Miljan and Marinković, Aleksandar",
year = "2018",
abstract = "15 symmetric 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides were synthesized in this work. Their structures were characterized using IR, H-1 and C-13 NMR, and UV-Vis spectroscopy. DFT calculations indicated that s-trans/s-trans conformation prevail in all compounds. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear solvation-free energy relationships (LSER), i.e., Kamlet-Taft and Catalan models. A linear free energy relationship (LFER) in the form of single substituent parameter equations (SSP) was used to postulate quantitative structure-property relations of substituent effect on NMR data. TD-DFT results showed dependence of electronic transition on the substituent effects. The push-pull character of these compounds was analyzed by differences in C-13 chemical shift of the ethylenic double bond in 2- and 6-positions of cross-conjugated with pyridinum central ring. Also, the quotient of the occupations for the bonding pi and anti-bonding pi* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with pi*/pi and C-13 chemical shift differences of the bridging group proved them to be adequate descriptor of push-pull character. Synthesized compounds were screened for the antioxidant activity, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical methods, and results demonstrated moderate antioxidant potential.",
publisher = "Springer, New York",
journal = "Journal of the Iranian Chemical Society",
title = "Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides",
volume = "15",
number = "11",
pages = "2483-2501",
doi = "10.1007/s13738-018-1437-5"
}
Milošević, M. D., Prlainović, N. Z., Milčić, M. K., Nikolić, V., Božić, A. R., Bigović, M.,& Marinković, A.. (2018). Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides. in Journal of the Iranian Chemical Society
Springer, New York., 15(11), 2483-2501.
https://doi.org/10.1007/s13738-018-1437-5
Milošević MD, Prlainović NZ, Milčić MK, Nikolić V, Božić AR, Bigović M, Marinković A. Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides. in Journal of the Iranian Chemical Society. 2018;15(11):2483-2501.
doi:10.1007/s13738-018-1437-5 .
Milošević, Milena D., Prlainović, Nevena Z., Milčić, Miloš K., Nikolić, Vesna, Božić, Aleksandra R., Bigović, Miljan, Marinković, Aleksandar, "Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides" in Journal of the Iranian Chemical Society, 15, no. 11 (2018):2483-2501,
https://doi.org/10.1007/s13738-018-1437-5 . .
2
1
2
1

Supplementary material for the article: Rančić, M. P.; Stojiljković, I.; Milošević, M.; Prlainović, N.; Jovanović, M.; Milčić, M. K.; Marinković, A. D. Solvent and Substituent Effect on Intramolecular Charge Transfer in 5-Arylidene-3-Substituted-2,4-Thiazolidinediones: Experimental and Theoretical Study, 2016. https://doi.org/10.1016/j.arabjc.2016.12.013

Rančić, Milica; Stojiljković, Ivana N.; Milošević, Milena D.; Prlainović, Nevena Z.; Jovanović, Maja; Milčić, Miloš K.; Marinković, Aleksandar

(2016)

TY  - DATA
AU  - Rančić, Milica
AU  - Stojiljković, Ivana N.
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Jovanović, Maja
AU  - Milčić, Miloš K.
AU  - Marinković, Aleksandar
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3613
T2  - Arabian Journal of Chemistry
T1  - Supplementary material for the article: Rančić, M. P.; Stojiljković, I.; Milošević, M.; Prlainović, N.; Jovanović, M.; Milčić, M. K.; Marinković, A. D. Solvent and Substituent Effect on Intramolecular Charge Transfer in 5-Arylidene-3-Substituted-2,4-Thiazolidinediones: Experimental and Theoretical Study, 2016. https://doi.org/10.1016/j.arabjc.2016.12.013
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3613
ER  - 
@misc{
author = "Rančić, Milica and Stojiljković, Ivana N. and Milošević, Milena D. and Prlainović, Nevena Z. and Jovanović, Maja and Milčić, Miloš K. and Marinković, Aleksandar",
year = "2016",
journal = "Arabian Journal of Chemistry",
title = "Supplementary material for the article: Rančić, M. P.; Stojiljković, I.; Milošević, M.; Prlainović, N.; Jovanović, M.; Milčić, M. K.; Marinković, A. D. Solvent and Substituent Effect on Intramolecular Charge Transfer in 5-Arylidene-3-Substituted-2,4-Thiazolidinediones: Experimental and Theoretical Study, 2016. https://doi.org/10.1016/j.arabjc.2016.12.013",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3613"
}
Rančić, M., Stojiljković, I. N., Milošević, M. D., Prlainović, N. Z., Jovanović, M., Milčić, M. K.,& Marinković, A.. (2016). Supplementary material for the article: Rančić, M. P.; Stojiljković, I.; Milošević, M.; Prlainović, N.; Jovanović, M.; Milčić, M. K.; Marinković, A. D. Solvent and Substituent Effect on Intramolecular Charge Transfer in 5-Arylidene-3-Substituted-2,4-Thiazolidinediones: Experimental and Theoretical Study, 2016. https://doi.org/10.1016/j.arabjc.2016.12.013. in Arabian Journal of Chemistry.
https://hdl.handle.net/21.15107/rcub_cherry_3613
Rančić M, Stojiljković IN, Milošević MD, Prlainović NZ, Jovanović M, Milčić MK, Marinković A. Supplementary material for the article: Rančić, M. P.; Stojiljković, I.; Milošević, M.; Prlainović, N.; Jovanović, M.; Milčić, M. K.; Marinković, A. D. Solvent and Substituent Effect on Intramolecular Charge Transfer in 5-Arylidene-3-Substituted-2,4-Thiazolidinediones: Experimental and Theoretical Study, 2016. https://doi.org/10.1016/j.arabjc.2016.12.013. in Arabian Journal of Chemistry. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3613 .
Rančić, Milica, Stojiljković, Ivana N., Milošević, Milena D., Prlainović, Nevena Z., Jovanović, Maja, Milčić, Miloš K., Marinković, Aleksandar, "Supplementary material for the article: Rančić, M. P.; Stojiljković, I.; Milošević, M.; Prlainović, N.; Jovanović, M.; Milčić, M. K.; Marinković, A. D. Solvent and Substituent Effect on Intramolecular Charge Transfer in 5-Arylidene-3-Substituted-2,4-Thiazolidinediones: Experimental and Theoretical Study, 2016. https://doi.org/10.1016/j.arabjc.2016.12.013" in Arabian Journal of Chemistry (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3613 .

Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study

Rančić, Milica; Stojiljković, Ivana N.; Milošević, Milena D.; Prlainović, Nevena Z.; Jovanović, Maja; Milčić, Miloš K.; Marinković, Aleksandar

(2016)

TY  - JOUR
AU  - Rančić, Milica
AU  - Stojiljković, Ivana N.
AU  - Milošević, Milena D.
AU  - Prlainović, Nevena Z.
AU  - Jovanović, Maja
AU  - Milčić, Miloš K.
AU  - Marinković, Aleksandar
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/305
AB  - The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-arylidene-3-methyl-2,4-thiazolidinediones (series 1) and 5-arylidene-3-phenyl-2,4-thiazolidinediones (series 2) was studied by using experimental and theoretical methodology. The effect of specific and non-specific solvent-solute interactions on the UV-vis absorption maxima shifts was evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and 13C NMR data by using SSP (single substituent parameter) and DSP (dual substituent parameters). Comparative LFER analysis of 10 styrenic series was performed in order to distinguish contribution of structural and electronic substituent effect on extent of π-polarization in a side chain (vinyl) group. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. TD-DFT calculations are performed to quantify the efficiency of intramolecular charge transfer (ICT) allowing us to define the charge-transfer distance (DCT), amount of transferred charge (QCT), and difference of dipole moments between the ground and excited states (μCT). It was found that both substituents and solvents influence electron density shift, i.e. extent of conjugation, and affect intramolecular charge transfer character in the course of excitation. © 2016 The Authors.
T2  - Arabian Journal of Chemistry
T1  - Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study
DO  - 10.1016/j.arabjc.2016.12.013
ER  - 
@article{
author = "Rančić, Milica and Stojiljković, Ivana N. and Milošević, Milena D. and Prlainović, Nevena Z. and Jovanović, Maja and Milčić, Miloš K. and Marinković, Aleksandar",
year = "2016",
abstract = "The substituent and solvent effect on intramolecular charge transfer (ICT) in 5-arylidene-3-methyl-2,4-thiazolidinediones (series 1) and 5-arylidene-3-phenyl-2,4-thiazolidinediones (series 2) was studied by using experimental and theoretical methodology. The effect of specific and non-specific solvent-solute interactions on the UV-vis absorption maxima shifts was evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. Linear free energy relationships (LFERs) have been applied to the UV-vis and 13C NMR data by using SSP (single substituent parameter) and DSP (dual substituent parameters). Comparative LFER analysis of 10 styrenic series was performed in order to distinguish contribution of structural and electronic substituent effect on extent of π-polarization in a side chain (vinyl) group. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. TD-DFT calculations are performed to quantify the efficiency of intramolecular charge transfer (ICT) allowing us to define the charge-transfer distance (DCT), amount of transferred charge (QCT), and difference of dipole moments between the ground and excited states (μCT). It was found that both substituents and solvents influence electron density shift, i.e. extent of conjugation, and affect intramolecular charge transfer character in the course of excitation. © 2016 The Authors.",
journal = "Arabian Journal of Chemistry",
title = "Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study",
doi = "10.1016/j.arabjc.2016.12.013"
}
Rančić, M., Stojiljković, I. N., Milošević, M. D., Prlainović, N. Z., Jovanović, M., Milčić, M. K.,& Marinković, A.. (2016). Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study. in Arabian Journal of Chemistry.
https://doi.org/10.1016/j.arabjc.2016.12.013
Rančić M, Stojiljković IN, Milošević MD, Prlainović NZ, Jovanović M, Milčić MK, Marinković A. Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study. in Arabian Journal of Chemistry. 2016;.
doi:10.1016/j.arabjc.2016.12.013 .
Rančić, Milica, Stojiljković, Ivana N., Milošević, Milena D., Prlainović, Nevena Z., Jovanović, Maja, Milčić, Miloš K., Marinković, Aleksandar, "Solvent and substituent effect on intramolecular charge transfer in 5-arylidene-3-substituted-2,4-thiazolidinediones: Experimental and theoretical study" in Arabian Journal of Chemistry (2016),
https://doi.org/10.1016/j.arabjc.2016.12.013 . .
9
4
7
6