Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides
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2018
Authors
Milošević, Milena D.Prlainović, Nevena
Milčić, Miloš
Nikolić, Vesna
Božić, Aleksandra R.
Bigović, Miljan
Marinković, Aleksandar
Article (Published version)
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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 quotie...nt 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.
Keywords:
Solvatochromism / Kamlet-Taft / Catalan / Antioxidant activitySource:
Journal of the Iranian Chemical Society, 2018, 15, 11, 2483-2501Publisher:
- Springer, New York
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
DOI: 10.1007/s13738-018-1437-5
ISSN: 1735-207X
WoS: 000444188800007
Scopus: 2-s2.0-85052993656
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Milošević, Milena D. AU - Prlainović, Nevena AU - Milčić, Miloš AU - Nikolić, Vesna AU - Božić, Aleksandra R. AU - Bigović, Miljan AU - Marinković, Aleksandar PY - 2018 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3843 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 EP - 2501 IS - 11 SP - 2483 VL - 15 DO - 10.1007/s13738-018-1437-5 ER -
@article{ author = "Milošević, Milena D. and Prlainović, Nevena and Milčić, Miloš 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", pages = "2501-2483", number = "11", volume = "15", doi = "10.1007/s13738-018-1437-5" }
Milošević, M. D., Prlainović, N., Milčić, M., 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 N, Milčić M, 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, Milčić, Miloš, 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 . .