Synthesis, spectroscopic characterization and crystallographic behavior of ethyl 2-(4-methyl-(2-benzylidenehydraziny1))thiazole-4-carboxylate: Experimental and theoretical (DFT) studies

Abstract

The ethyl 2-(4-methyl-(2-benzylidenehydrazinyl))thiazole-4-carboxylate (1) was synthesized via reaction of 4-methyl-(1-benzylidenehydrazinyl)-2-carbothioamide with ethyl bromopyruvate. The compound is characterized by FTIR and NMR before being analyzed by X-ray diffraction method. These properties of the structure are further investigated by DFT quantum chemical methods. The molecular geometry of the compound (1) was optimized using density functional theory (DFT/B3LYP) method with the cc-pVTZ basis sets in ground state. The MEP map exhibits the negative potential sites are on electronegative atoms and the positive potential sites around the hydrogen atoms. The MEP and Mulliken population analysis confirm the hydrogen bonding sites in the molecule. We have also calculated geometric parameters (bond lengths, bond angles, torsion angles), vibrational assignments and chemical shifts of the compound (1) theoretically and compared with the experimental data, these values are found in good agreement with each other. Although theoretical calculations were carried out in gas phase, however no significant differences were found in these values.