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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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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, 1H and 13C 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 Catalán 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 13C 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 π and anti-bonding π* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with π*/π and 13C 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.

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Acknowledgements

The authors acknowledge financial support from the Ministry of Education, Science and Technological development of Serbia, Project no. ОI 172013.

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Authors and Affiliations

  1. Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000, Belgrade, Serbia

    Milena D. Milošević & Aleksandar D. Marinković

  2. Innovation Centre of Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000, Belgrade, Serbia

    Nevena Ž. Prlainović

  3. Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000, Belgrade, Serbia

    Miloš Milčić & Vesna Nikolić

  4. Belgrade Polytechnic, Brankova 17, 11000, Belgrade, Serbia

    Aleksandra Božić

  5. Faculty of Science and Mathematics, University of Montenegro, Bulevar Džordža Vašingtona bb, 81000, Podgorica, Montenegro

    Miljan Bigović

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  1. Milena D. Milošević
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Milošević, M.D., Prlainović, N.Ž., Milčić, M. et al. Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides. J IRAN CHEM SOC 15, 2483–2501 (2018). https://doi.org/10.1007/s13738-018-1437-5

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