Abstract
In the current investigation, the molecular structure of the anticonvulsant agent (2E)-2-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]-N-phenylhydrazinecarboxamide ((2E)-HIPC) was theoretically modelled using ab initio Hartree-Fock (HF) and density functional theory (DFT/B3LYP) calculations. The Fourier transform (FT) infrared and FT-Raman spectra of (2E)-HIPC were also recorded, and the observed bands were assigned to the vibrational normal modes. The main functional groups were identified via vibrational analysis, and their absorption bands were assigned. A comparative analysis was performed for the computed and experimental results. Subtle differences were observed between the calculated and experimental UV-Vis spectra. Time-dependent density functional theory (TD-DFT) excitation energies were calculated for five excited electronic states. The calculations were applied to simulate the spectra of (2E)-HIPC, and these simulated spectra exhibited excellent agreement with the experimental spectra. The DFT/B3LYP/6-311++G(d,p) method, after scaling, exhibited better agreement with the experimental values than the results obtained by the HF method. The energy, oscillator strength, and wavelength computed by TD-DFT (IEFPCM) are consistent with the experimental results. The molecular electrostatic potential (MEP) and frontier molecular orbitals (HOMO-LUMO) were also determined to enable prediction of the structural changes and reactive sites. Mulliken population charges of the title molecule were also calculated in the gas phase. The NMR chemical shifts (13C and 1H) were calculated using the gauge-including atomic orbital method and the B3LYP/6-311++G(d,p) approach and were compared with the experimental values.
Highlights
Epilepsy as a disease can be described as a group of serious brain disorders affecting people of all ages
(13C and 1H) chemical shifts of the title molecule were computed by the gauge-including atomic orbital method using B3LYP/6-311++G(d,p) calculations, and the theoretical results were compared with the experimental values
DMSO and acetonitrile solvents were used in the DFT/B3LYP/IEFPCM calculations to improve the prediction of the NMR values and achieve good accuracy
Summary
Epilepsy as a disease can be described as a group of serious brain disorders affecting people of all ages It is characterized by the onset of spontaneous convulsive and non-convulsive seizures. (2E)-2-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]-N-phenylhydrazinecarboxamide ((2E)-HIPC) is a hybrid structure incorporating both imidazole and arylsemicarbazone moieties that act as pharmacophore scaffolds in some candidate anticonvulsants [9,10]. This compound has exhibited anticonvulsant activity with 16% seizure protection at a dose level of 750 μmol/kg in a subcutaneous pentylenetetrazole (scPTZ) screen with no neurotoxicity [11]. (13C and 1H) chemical shifts of the title molecule were computed by the gauge-including atomic orbital method using B3LYP/6-311++G(d,p) calculations, and the theoretical results were compared with the experimental values
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