Experimental and theoretical characterization of chelidonic acid structure

Abstract Chelidonic acid (4-oxo-4H-pyran-2,6-dicarboxylic acid) is present in plants of Papaveraceae family, especially Chelidonium majus . Due to its anticancer, antibacterial, hepatoprotective, and antioxidant properties, it has been used medical treatments. In this work, the X-ray structure methanol solvate chelidonic was determined. Layers are held by hydrogen bonds via COOH C = O fragments additionally bridged methanol. The formed H-bond network between two units different from typical –COOH dimers observed, e.g., crystals isophtalic acid. molecular 2,6-dimethyl-γ-pyrone (2Me4PN) acid, a 2,6-dicarboxylic derivate γ-pyrone (4PN), verified silico using density functional theory (DFT-B3LYP) combined with large correlation-consistent basis sets. impact –CH 3 substituents on 4PN ring structure, dipole moments, geometric/magnetic indexes aromaticity, NBO charges assessed following unconstrained geometry optimization gas phase, chloroform, methanol, DMSO, water solvent effect introduced polarized continuous model (PCM). acid–methanol complex analyzed their interaction energy estimated. Theoretical modeling enabled prediction accurate structural parameters, aromaticity studied 4PN, 2Me4PN, molecules.