Synthesis, spectroscopic investigation, molecular docking and DFT studies of novel (2Z,4Z)-2,4-bis(4-chlorobenzylidene)-5-oxo-1-phenylpyrrolidine-3-carboxylic acid (BCOPCA)

Abstract

The synthesized compound (2Z,4Z)-2,4-bis(4-chlorobenzylidene)-5-oxo-1-phenylpyrrolidine-3-carboxylic acid (BCOPCA) was characterised by Ultraviolet, FT-Infra Red, 1H, 13C Nuclear Magnetic Resonance and mass spectroscopy. The compound was further subjected to quantum chemical calculations at the level of density functional theory (DFT) using 6-31G (d,p) basis sets method with B3LYP and CAM-B3LYP hybrid functionals. The intramolecular interactions, polarizability, hyperpolarizability and nonlinear optical properties of the title compound were also incorporated in the study. The total first static hyperpolarizability (β0 = 19.477 × 10−30 and 16.924 × 10−30 esu) value was also computed and indicated the title molecule as an interesting forthcoming NLO material. The other thermodynamic properties (entropy, heat capacity and zero vibrational energy) were also discussed. The study also includes NBO computations, complete vibrational assignments, Mulliken charges, UV–Visible spectral analysis and HOMO–LUMO energies. The regions of low and high electron density were obtained from MESP and ESP maps. The calculated parameters for BCOPCA using aforementioned functions are harmonious with the experimental findings. The in-vitro antimicrobial activity and molecular docking studies of BCOPCA were also done and showed a good correlation.

A detailed computational investigation on the structural and spectroscopic properties of propolisbenzofuran B

“…Red colour displays nucleophilic area while blue displays electrophilic area [35, 36, 37, 38]. The yellow, green and light blue colours characterized somewhat electron rich; neutral and somewhat electron defective areas, respectively [39, 40]. It can be seen that oxygen atoms in C=O and C–O bonds have maximum negative electrostatic potential due to their considerable intrinsic electronegative characteristic.…”

Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives

“…Related to C=O bands, two carbonyl groups are presented: C=O for the carbonyl of the acid moiety, which is displayed at 1738 cm −1 for 3a and 1730 cm −1 for 3b as medium bands. In this sense, Devi et al [59] detected this band at 1766 cm −1 ; Devi et al [60] reported this band at 1729 cm −1 . For C=O, the carbonyl of the ketone moiety is displayed as medium bands at 1621 cm −1 for 3a and 1617 cm −1 for 3b; this band is easily to identify due to higher strength and conjugation with the double bonds C5=C6 or C3=C4.…”

“…These values are according to those reported by Devi et al [59] at 3634 cm −1 using the B3LYP method with a 6-31G(d,p) basis set. Also, Devi et al [60] reported the value for OH at 3545 cm −1 .…”