TY  - JOUR
AU  - Milošević, Milena
AU  - Prlainović, Nevena
AU  - Milčić, Miloš
AU  - Nikolić, Vesna
AU  - Božić, Aleksandra
AU  - Bigović, Miljan
AU  - Marinković, Aleksandar
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6959
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
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 and Prlainović, Nevena and Milčić, Miloš and Nikolić, Vesna and Božić, Aleksandra 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",
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., Prlainović, N., Milčić, M., Nikolić, V., Božić, A., 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., 15(11), 2483-2501.
https://doi.org/10.1007/s13738-018-1437-5

Milošević M, Prlainović N, Milčić M, Nikolić V, Božić A, 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, Prlainović, Nevena, Milčić, Miloš, Nikolić, Vesna, Božić, Aleksandra, 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 . .