Synthesis, crystal structure, and DFT calculations of 2H-1,3-benzodioxol-5-yl 3-(4-hydroxy-3-methoxyphenyl) prop-2-enoate

Abstract

Abstract Small molecule, 2H-1,3-benzodioxol-5-yl 3-(4‑hydroxy-3-methoxyphenyl) prop‑2-enoate (FA-SES), is a combination of phytonutrients, ferulic acid and sesamol, useful in CVD by inhibition of myeloperoxidase enzyme. The molecule was synthesized and structural characterization was performed by FT-IR, 1H & 13C NMR, and LC-MS/MS techniques. Additionally, the structure was elucidated by a single crystal X-ray data. The compound C17H14O6 is the monoclinic crystal structure with P21/c offered C H•••π and C•••O H hydrogen bonding interactions, appropriate bond length, and other related parameters. Further, the molecule was evaluated for intermolecular interactions by Hirshfeld surface analysis. DFT calculation (B3LYP method) was performed to determine its geometrical and electronic parameters which can be useful to assess its utility in biological applications. The HOMO, LUMO, bandgap energy and dipole moment values showed -5.67 eV, -1.94 eV, 3.73 eV and 4.77 Debye respectively. Single-crystal data and DFT results are unequivocally comparable in all parameters.