SYNTHESIS, SPECTROSCOPY, X-RAY CRYSTALLOGRAPHY, AND DFT CALCULATIONS OF ( E )-4-{[(2-HYDROXYPHENYL) IMINO]METHYL}PHENYL
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SYNTHESIS, SPECTROSCOPY, X-RAY CRYSTALLOGRAPHY, AND DFT CALCULATIONS OF (E)-4-{[(2-HYDROXYPHENYL) IMINO]METHYL}PHENYL BENZENESULFONATE N. Özdemi1* and O. Dayan2
The title molecule is prepared by the Schiff base reaction. The structural properties of the compound are described using FTIR, 1H and 13C NMR, and absorption spectroscopies and single-crystal X-ray diffraction. Some quantum chemical calculations of the compound (molecular structure, vibrational wavenumbers and gauge including atomic orbital, 1H and 13C NMR chemical shifts) are executed using the density functional theory method at the B3LYP/6-311++G(d,p) level of theory. Additionally, electronic spectra of the compound are computed using the time-dependent density functional theory (TDDFT) method under the above conditions. A comparison of the experimental and theoretical findings reveals that a good correlation between them is acquired. DOI: 10.1134/S0022476620100091 Keywords: benzenesulfonate, X-ray structure, spectroscopy, DFT calculation.
INTRODUCTION Schiff bases may be easily prepared by the reaction between primary amines and aldehydes/ketones. Schiff bases are continuously attracting much attention in the literature because of their biological activities, ligand behavior, and optical properties. For example, recent studies of Schiff bases have shown to exhibit anticancer, antibacterial, antifungal, and antimicrobial activities [1-5]. Similarly, Schiff bases are good ligands, especially for transition metals and their complexes frequently used as catalysts, optical materials, etc. [6-9]. The attachment of a functional group to Schiff bases markedly affects the material properties in all of those examples. Among many Schiff bases known in the literature, the ones bearing sulfonate groups are rare. The molecules including sulfonate groups have recently attracted much attention because of promising properties for optical, biological, and catalytic applications [10-13]. In this work, we synthesized a new Schiff base with an arensulfonate group by the reaction of 4-formylphenyl benzenesulfonate and 2-aminophenol in ethanol, and characterized it by structural and spectroscopic techniques. Additionally, some parameters were theoretically investigated at the B3LYP/6–311++G(d,p) level to provide a deeper understanding of its chemical behavior.
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Department of Mathematics and Science Education, Faculty of Education, Ondokuz Mayıs University, Samsun, Republic of Turkey; *[email protected]. 2Department of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, Çanakkale, Republic of Turkey. Original article submitted April 14, 2020; revised April 14, 2020; accepted April 27, 2020. 0022-4766/20/6110-1575 © 2020 by Pleiades Publishing, Ltd.
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MATERIALS AND METHODS Instrumentation. All chemicals were purchased from commercial sources and used as received. The instruments used are as follows: for NMR spectra JEOL JNM-ECX400 II (400 MHz for 1H NMR and 100 MHz for 13C NMR, CDCl3 as a solvent and tetramethylsilane as the internal reference)
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