Abstract
This study reports the synthesis of the novel crystalline 4-phenyl-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-1H-1,2,4-triazole-5(4H)-thione compound in an excellent yield via multi-steps reactions. Probability of the thiol⇔thione tautomerism reaction occurrence via single-proton intramigration for NH to nearby CS was DFT-theoretically monitored. The thione tautomer isomer structure formation was supported by X-ray single crystal measurement, the lowest energy DFT-optimized structures of the molecule in gas-phase reconcile with the thionic tautomer structure solved by X-ray technique. Several physico-chemically tools like CHN-elemental analyses, FT-IR, MS, TG/DTG, XRD, UV–Vis.,1H and 13C NMR were served for the compound characterization. Experimental methods X-ray diffraction, NMR, UV–Vis. and FT-IR spectroscopy and their corresponding quantum-parameters were computed for their electronic and structural output. The computed Hirshfeld surface analysis (HSA) and molecular electrostatic potential (MEP) reflected the presence of several H-bonds and CH…π (CC) as short contacts which was detected experimentally by XRD-packing analysis.
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•Novel 1,2,4-triazole-5(4H)-thione derivative tautomer was prepared and XRD characterized.•Experimentally, the thione-tautomer structure was spectrally and thermally analyzed.•Experimental data were successfully explained based on DFT-computational calculation.•The thiol⇔thione H-intramigration tautomerism via QST2/TS method was computed.