Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides
Authorized Users Only
2018
Authors
Milošević, Milena D.Prlainović, Nevena Z.
Milčić, Miloš K.
Nikolić, Vesna
Božić, Aleksandra R.
Bigović, Miljan
Marinković, Aleksandar
Article (Published version)
Metadata
Show full item recordAbstract
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-MESTD-Basic Research (BR or ON)-172013)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3255
DOI: 10.1007/s13738-018-1437-5
ISSN: 1735-207X
WoS: 000444188800007
Scopus: 2-s2.0-85052993656
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - 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 . .