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Spectroscopic and Theoretical Studies and Intramolecular Proton Transfer in (Z)-2-Hydroxy-6-(((2-methoxy-5-(trifluoromethyl)phenyl)amino)methylene)cyclohexa-2,4-dien-1-one

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Abstract

In present work, a new Schiff base compound, (E)-3-(((2-methoxy-5-(trifluoromethyl)phenyl)imino)methyl)benzene-1,2-diol was synthesized and characterized by X-ray diffraction and spectroscopic methods (FT-IR, UV–Vis) and quantum mechanical calculation methods. The obtained structure is monoclinic, space group P21/c, with unit cell parameters a = 15.1881(10) Å, b = 14.5816(11) Å, c = 6.2023(5) Å, β = 98.008 (6)°, and Z = 4. Theoretical calculations were used to investigate the optimized molecular geometry of the title compound. The calculated and experimental results show the title compound tends to the keto-amine form. Besides, the frontier molecular orbital, non-linear optical properties and electronic structure parameters of the title compound were computed in the solvent media using the theoretical methods. The molecular electrostatic potential surface was obtained at the optimized geometry to predict reactive sites for nucleophilic and electrophilic attack for the studied molecule. Statistical thermodynamic functions for the title compound were calculated at 298.15 K temperature and 1 atm pressure by using the HF and DFT/B3LYP methods with the 6-311++G(d,p) basis set.

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ACKNOWLEDGMENTS

This study was supported by Ondokuz Mayıs University (project no. PYO.FEN.1906.19.001).

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Authors and Affiliations

  1. Vezirköprü Vocational School, Ondokuz Mayis University, Samsun, Turkey

    Gonca Özdemir Tarı

  2. Department of Science Education, Sinop University, Sinop, Turkey

    Başak Koşar Kırca

  3. Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, Samsun, Turkey

    Mahmut Taşdoğan & Erbil Ağar

  4. Department of Mathematics and Science Education, Faculty of Education, Ondokuz Mayıs University, Samsun, Turkey

    Namık Özdemir

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  1. Gonca Özdemir Tarı
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  2. Başak Koşar Kırca
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  4. Namık Özdemir
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  5. Erbil Ağar
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Correspondence to Gonca Özdemir Tarı, Başak Koşar Kırca, Mahmut Taşdoğan or Namık Özdemir.

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Tarı, G., Kırca, B.K., Taşdoğan, M. et al. Spectroscopic and Theoretical Studies and Intramolecular Proton Transfer in (Z)-2-Hydroxy-6-(((2-methoxy-5-(trifluoromethyl)phenyl)amino)methylene)cyclohexa-2,4-dien-1-one. Russ. J. Phys. Chem. 95, 1621–1631 (2021). https://doi.org/10.1134/S0036024421080252

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