Synthesis, characterization, quantum chemical calculations and evaluation of antioxidant properties of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids

A series of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids were synthesized, and their structures were elucidated by the UV, IR, 1H NMR, 13C NMR spectroscopies and elemental analysis. The UV and IR calculations of the molecules were performed by using B3LYP, HF and MP2 metho...

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Bibliographic Details
Published in:Journal of molecular structure 2017-04, Vol.1134, p.40-50
Main Authors: Gür, Mahmut, Muğlu, Halit, Çavuş, M. Serdar, Güder, Aytaç, Sayıner, Hakan S., Kandemirli, Fatma
Format: Article
Language:English
Subjects:
1,3,4-Thiadiazole
Antioxidant properties
Computational chemistry
Density functional theory
Methoxy-cinnamic acid
Radical scavenging activities
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Summary:A series of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids were synthesized, and their structures were elucidated by the UV, IR, 1H NMR, 13C NMR spectroscopies and elemental analysis. The UV and IR calculations of the molecules were performed by using B3LYP, HF and MP2 methods with selected 6-311++G(2d,2p), 6-311++G(3df,3pd) and cc-pvtz basis sets. Dipole moment, polarizability, chemical hardness/softness and electronegativity were also calculated and analyzed. Experimental FT-IR spectra and UV–Vis spectrum of the compounds were compared with theoretical data. Furthermore, antioxidant activities of the compounds were practised via different test methods such as 2,2-diphenyl-1-picryl-hydrazyl (DPPH), N,N-dimethyl-p-phenylenediamine (DMPD+), and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS+) scavenging activity assays. When compared with standards (BHA-Butylated hydroxyanisole, RUT-Rutin, and TRO-Trolox), it was observed that especially XIII and XIV which include methoxy groups at the o- and m-positions, respectively, had effective activities. [Display omitted] •1,3,4-thiadiazole derivatives from 2-methoxy or 3-methoxycinnamic acid were synthesized.•The molecules have been identified by UV, IR, 1H NMR, 13C NMR spectroscopies and elemental analysis.•The antioxidant properties were investigated.•The quantum chemical calculations were performed by some methods and basis sets on Gaussian 09.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2016.12.041