Synthesis, crystal structure, and DFT study of 4-((furan-2-ylmethyl)amino)benzoic acid and N'-acryloyl-N'-phenylfuran-2-carbohydrazide compounds

Abstract

4-((furan-2-ylmethyl)amino)benzoic acid and N'-acryloyl-N'-phenylfuran-2-carbohydrazide are important intermediates for the synthesis of furan compounds with furan ring. In this paper, the title compounds were obtained by two-step reaction respectively. The structures of the title compounds were confirmed by FTIR, 1H and 13C NMR spectroscopy, and mass spectrometry. At the same time, single crystals of the title compounds were measured by X-ray diffraction and subjected to crystallographic and conformational analyses. The molecular structures were further calculated using density functional theory (DFT), which were compared with the X-ray diffraction value. The results of the conformational analysis indicate that the molecular structures optimized by DFT were consistent with the crystal structures determined by single crystal X-ray diffraction. In addition, the molecular electrostatic potential and frontier molecular orbitals of the title compounds are further investigated by DFT, and some physicochemical properties of the compounds are revealed.