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Synthesis, Spectroscopic and Computational Analysis of 2-[(2-Sulfanyl-1H-benzo[d]imidazol-5-yl)iminomethyl]phenyl Naphthalene-2-sulfonate

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Abstract

2-[(2-Sulfanyl-1H-benzo[d]imidazol-5-yl)iminomethyl]phenyl naphthalene-2-sulfonate was obtained as a result of the reactions of 5-amino-2-sulfanylbenzimidazole with 2-(2-naphthylsulfonyloxy)benzaldehyde. The newly synthesized compound was characterized using IR, 1H and 13C NMR spectroscopy. Theoretical investigations of the thione–thiol tautomerism of the molecule were performed using DFT/ B3LYP calculations with the 6-311++G(d,p) basis set. The NMR chemical shifts were calculated by the gauge-invariant atomic orbital (GIAO) method and compared with the experimental data. Additionally, the frontier molecular orbital (HOMO-LUMO), MEP, and NLO analyses were performed for the optimized structure. The NLO analysis showed that the thiol form of the molecule is more stable than the thione form and is a good non-linear optical compound.

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ACKNOWLEDGMENTS

This study was supported by the Kafkas University Scientific Research Projects Coordination (project no. 2014-MMF-43).

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Authors and Affiliations

  1. Kars Vocational School, Kafkas University, 36100, Kars, Turkey

    G. Kotan

  2. Vocational School of Health Services, Giresun University, 28200, Giresun, Turkey

    H. Gökce

  3. Department of Chemical Engineering, Faculty of Engineering and Architecture, Kafkas University, 36100, Kars, Turkey

    O. Akyıldırım

  4. Department of Chemistry, Kafkas University, 36100, Kars, Turkey

    H. Yüksek, M. Beytur, S. Manap & H. Medetalibeyoğlu

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Kotan, G., Gökce, H., Akyıldırım, O. et al. Synthesis, Spectroscopic and Computational Analysis of 2-[(2-Sulfanyl-1H-benzo[d]imidazol-5-yl)iminomethyl]phenyl Naphthalene-2-sulfonate. Russ J Org Chem 56, 1982–1994 (2020). https://doi.org/10.1134/S1070428020110135

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