Experimental spectroscopic, Quantum computational, Hirshfeld surface and molecular docking studies on 3-Pyridinepropionic acid

Abstract

• Experimental spectra (UV-Vis, 1 H and 13 C NMR) of 3-PPIA were done and compared. • PED, MEP surface, ELF diagram, and NLO analysis were achieved successfully. • FMO and UV-Vis, NBO, NHO, and Population analysis studies were done. • Hirshfeld surface analysis and thermodynamic parameters (G, H, S) were analyzed. • Docking with two Receptors was done with -6.6 and -6.2 kcal/mol binding energy. 3-pyridine propionic acid (3-PPIA) was studied experimentally by UV-Vis, 1 H NMR, 13 C NMR spectroscopy and Quantum computationally by density functional theory approach. The B3LYP/6–311++G(d,p) basis set used to get the optimized structure, vibrational frequencies, and other various parameters. Calculated bond lengths and angles were compared with the experimental bond lengths and Bond angle Parameters. 3D Hirshfeld surface and 2D fingerprint plots were drawn by using Crystal Explorer software. The HOMO/LUMO energy gap results indicated that, adequate charge transfer was happening within the molecule. ELF was drawn to find the degree of relative localization of electrons. The NBO analysis was done to study donor and acceptor interactions. The MEP surface was drawn in 3-D colour coding and Fukui functions were analyzed to find possible sites to attack by different substituents. TD-DFT method and PCM solvent model was employed for electronic property analysis such as UV-Vis (in gas phase, ethanol and DMSO) and compared with the experimental UV-Vis spectra done in DMSO and Methanol. 2D Hirshfeld surface was drawn to study intermolecular interactions in detail and 2D finger print plots were drawn for analysis of percentage of interaction in between atoms, it revealed that 3-PPIA was stabilized mainly by formation of H—H/H—O/C—H contacts. The drug-likeness study was carried out on the ligand molecule and its derivatives, indicated drug like nature of 3-PPIA. Molecular docking was done to study interaction between ligand and proteins with two protein receptors 4JIR and 5OUO , and found binding energies -6.6 and -6.2 kcal/mol, showed to have potential application in the medical field. This study could be used in the future for further development of pharmacological active based on 3-pyridinepropionic acid.