Quantum computational, Spectroscopic investigations on benzofuranylcarbonylpyrazolopyridine by DFT/TD-DFT: Synthesis, Structure, NBO and NLO research

Abstract

Reaction of 4-methoxy-5-oxo-5H-furo[3,2-g] chromene-6-carboxaldehyde (1) with 5-amino-2,4-dihydro-3H-pyrazol-3-one (2) afforded the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-3-hydroxy-1H-pyrazolo[3,4-b]pyridine (3, BFCPP). The experimental and theoretical quantum computations (optimized structure, IR, NMR and UV-Vis.) investigation of the current compound were performed using DFT theory at B3LYP functional and 6–311++G(d,p) basis set. The complete analysis of the vibrational spectra was taken with the aid of normal coordinate analysis followed by scaled quantum mechanical force field methodology. The theoretical NMR was achieved in DMSO-d6 as a solvent, while the IR and optimized calculations were done in the gas phase. A kind of solutions were used to discover the UV-Visible spectrum using the TD-DFT method. The stability of the current molecule occurred from hyper conjugative interactions leading to its nonlinear optical activity. Also, the charge delocalization was analyzed using natural bond orbital technique. Mulliken atomic charge and molecular electrostatic potential (MEP) are also calculated. HOMO–LUMO energy gap value indicates the probability of charge transfer within the molecule. The thermodynamic properties at different temperatures are also analyzed.