Experimental and theoretical studies on the structure and spectroscopic properties of (E)-1-(2-aminophenyl)-3-(pyridine-4-yl) prop-2-en-1-one

•Chalcones.•2-Aminochalcone was characterized by FT-IR, MS, 1H and 13C NMR.•PED analysis was used to assign 2-Aminochalcone calculated-vibrational frequencies.•The ab initio calculated HOMO energies show that orbitals are partially localized.•The ab initio calculated the LUMO energies show that orbitals are fully delocalized.

(E)-1-(2-aminophenyl)-3-(pyridine-4-yl)prop-2-en-1-one (or simply 2-aminochalcone) was synthetized and characterized by elemental analysis, FT-IR, NMR, MS and XRD. Molecular geometry optimization, vibrational harmonic frequencies, 1H and 13C NMR chemical shifts were calculated by ab initio (HF and MP2) and density functional theory (DFT) methods, with B3LYP and B3PW91 functionals, using GAUSSIAN 09 program package without any constraint on the geometry. With VEDA software vibrational frequencies were assigned in terms of the potential energy distribution. A detailed interpretation of the FT-IR, NMR and XRD, experimental and calculated, is reported. The HOMO and LUMO energy gap that reflects the chemical activity of the molecule were also studied by DFT and above basis set. All theoretical results correspond to a great extent to experimental ones.

Graphical abstractGraphical abstract A novel compound (E)-1-(2-aminophenyl)-3-(pyridine-4-yl)prop-2-en-1-one was synthesized, and its molecular structure was examined using computational and spectroscopic methods.Figure optionsDownload full-size imageDownload as PowerPoint slide