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Experimental and computational studies on zwitterionic (E)-2-(1-(2-(4-methylphenylsulfonamido)ethyliminio)ethyl) phenolate

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Abstract

The Schiff base compound (E)-2-(1-(2-(4-methylphenylsulfonamido)ethyliminio)ethyl) phenolate has been synthesised and characterized by IR, UV–Vis, and X-ray single-crystal determination. Ab initio calculations have been carried out for the title compound using the density functional theory (DFT) and Hartree–Fock (HF) methods at 6-31G(d) basis set. The calculated results show that the DFT/B3LYP and HF can well reproduce the structure of the title compound. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and the experimental ones is determined. Molecular orbital coefficient analyses reveal that the electronic transitions are mainly assigned to n → π* and π → π* electronic transitions. To investigate the tautomeric stability, optimization calculations at B3LYP/6-31G(d) level were performed for the NH and OH forms of the title compound. Calculated results reveal that the OH form is more stable than NH form. In addition, molecular electrostatic potential and NBO analysis of the title compound were performed at B3LYP/6-31G(d) level of theory.

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Authors and Affiliations

  1. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, 55139, Samsun, Turkey

    Gökhan Alpaslan, Hasan Tanak, Ahmet Erdönmez & Şamil Işık

  2. Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, 55139, Samsun, Turkey

    Ayşen Alaman Ağar

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  1. Gökhan Alpaslan
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  2. Hasan Tanak
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  4. Ahmet Erdönmez
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  5. Şamil Işık
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Correspondence to Hasan Tanak.

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Alpaslan, G., Tanak, H., Ağar, A.A. et al. Experimental and computational studies on zwitterionic (E)-2-(1-(2-(4-methylphenylsulfonamido)ethyliminio)ethyl) phenolate. Struct Chem 21, 1027–1036 (2010). https://doi.org/10.1007/s11224-010-9641-7

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