Title:The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro– Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3– alkyl–4–[3–methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro– 1H–1,2,4–triazol–5–one Molecules
VOLUME: 10 ISSUE: 6
Author(s):Halil Gokce, Semiha Bahceli, Onur Akyildirim, Haydar Yuksek and Ozlem Gursoy Kol
Affiliation:Physics Department, Faculty of Arts and Science, Suleyman Demirel University, 32260, Isparta, Turkey.
Keywords:1, 2, 4–triazol derivatives, Antioxidant activity, Vibrational spectroscopy, UV–vis spectroscopy, DFT/B3LYP
method, 1H and 13C NMR chemical shifts.
Abstract:The syntheses, antioxidant activities, acidity properties, experimental and theoretical investigations of vibrational
spectra (FT–IR and micro–Raman), 13C and 1H NMR chemical shifts and electronic properties of 3–alkyl–4–[3–
methoxy–4–(4–methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one (Me, Et and n–Pr) molecules
have been presented for the first time. The new compounds were analyzed for their potential antioxidant activities in
three different methods.The calculations of molecular structures, vibrational frequencies, 13C and 1H NMR chemical shifts
and electronic absorption wavelengths of the title molecules were computed by using the DFT/B3LYP method with 6–
31G(d) basis set which was used to have the structural and spectroscopic data about the mentioned molecules in the
ground state and the results calculated were compared with experimental values. Furthermore, gauge invariant atomic orbital
(GIAO) 1H and 13C NMR chemical shifts in different solvents (gas phase, DMSO and cholorofom), UV–vis. TD–
DFT calculations in ethanol solvent, the highest occupied molecular orbital (HOMO–1, HOMO), lowest unoccupied molecular
orbital (LUMO, LUMO+1), molecular electrostatic potential map (MEP), atomic charges and thermodynamic
properties of the title compounds have theoretically verified and simulated at the mentioned level. In addition, the calculated
infrared intensities and Raman activities of the compounds under study have also been reported.
