Crystal structure, spectral characterization, molecular modeling studies and structural effects of the proton transfer process for (E)-5-methoxy-2-[(3,4-dimethylphenylimino) methyl]phenol

Authors

  • Basak Kosar Kirca Sinop University
  • Gonca Ozdemir Tarı Ondokuz Mayıs University Vezirköprü Vocational School http://orcid.org/0000-0001-5919-1778
  • Cıgdem Albayrak Kastas Sinop University
  • Mustafa Odabasoglu Pamukkale University
  • Orhan Buyukgungor Ondokuz Mayıs University

DOI:

https://doi.org/10.20450/mjcce.2017.1295

Keywords:

Schiff base, prototropic tautomerism, intramolecular proton transfer, NLO, DFT

Abstract

The main purpose of this study is to characterize a new organic material, (E)-5-methoxy-2-[(3,4-dimethylphenylimino)methyl]phenol, which was synthesized and grown as a single crystal. The molecular structure and spectroscopic properties of the ortho-hydroxy Schiff base compound were determined by X-ray diffraction analysis, Fourier-transform infrared (FT-IR), ultraviolet-visible (UV-Vis) and nuclear magnetic resonance (NMR) spectroscopy techniques, experimentally and computationally with density functional theory (DFT) calculations. X-ray and UV-Vis studies show that the compound exists in an OH tautomeric form in the solid and solvent media. The gas phase geometry optimizations of two possible forms of the title compound, resulting from the prototropic tautomerism, were obtained using DFT calculations at the B3LYP/6-311G+(d,p) level of theory. A relaxed potential energy surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form by varying the redundant internal coordinate, the O-H bond distance. According to the PES scan process, the molecular geometry is strongly affected by the intramolecular proton transfer. The calculated first hyperpolarizability indicates that the compound could be a good material for non-linear optical applications. 

Author Biographies

Basak Kosar Kirca, Sinop University

Department of physics

Gonca Ozdemir Tarı, Ondokuz Mayıs University Vezirköprü Vocational School

Department of Physics

Cıgdem Albayrak Kastas, Sinop University

department of chemistry

Mustafa Odabasoglu, Pamukkale University

chemical technology program

Orhan Buyukgungor, Ondokuz Mayıs University

department of physics

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Published

2017-12-20

How to Cite

Kosar Kirca, B., Ozdemir Tarı, G., Albayrak Kastas, C., Odabasoglu, M., & Buyukgungor, O. (2017). Crystal structure, spectral characterization, molecular modeling studies and structural effects of the proton transfer process for (E)-5-methoxy-2-[(3,4-dimethylphenylimino) methyl]phenol. Macedonian Journal of Chemistry and Chemical Engineering, 36(2), 265–278. https://doi.org/10.20450/mjcce.2017.1295

Issue

Vol. 36 No. 2 (2017)

Section

Spectroscopy

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