Synthesis, antibacterial, antifungal and computational study of (E)-4-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxoprop-1-en-1-yl)benzonitrile

• Published in: Results in Chemistry 2022-01, Vol.4, p.100553, Article 100553
• Main Authors: Shinde, Rahul A., Adole, Vishnu A., Shinde, Rohit S., Desale, Bhatu S., Jagdale, Bapu S.
• Format: Article
• Language: English
• Subjects: Antimicrobial; Chalcone; DFT; FMO; UV–vis
• ISSN: 2211-7156; 2211-7156
• DOI: 10.1016/j.rechem.2022.100553

[Display omitted] •Synthesis and computational study of DHDOBN using DFT method.•FMO analysis of DHDOBN.•MESP and contour plot study.•Experimental and theoretical UV–vis and IR correlation.•Antimicrobial screening of the DHDOBN. In the present work, synthesis, antibacterial, antifungal and computational study of synthesized (E)-4-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxoprop-1-en-1-yl)benzonitrile (DHDOBN) chalcone derivative were explored. The computational study of the DHDOBN was performed using density functional theory (DFT) with B3LYP functional and 6-31G(d,p) basis set combination. Theoretical investigations about UV–vis and FT-IR spectral investigation of the DHDOBN was reported using TD-DFT/B3LYP/6-31G(d,p) and B3LYP/6-31G(d,p) levels, respectively. The computed UV–vis and FT-IR absorption spectral properties accord well with the outcomes of the experiments. The formation of the charge separation state as a result of the successful migration of electrons from the donor to acceptor unit through the π-bridge was confirmed by the analysis of electronic properties, including the frontier molecular orbitals (FMOs) analysis, molecular electrostatic surface potential (MESP), hole density distribution (HDD), and electron density distribution (EDD) map. highest occupied molecular orbital (HOMO) and lowest occupied molecular orbital (LUMO) energy values were used to compute the ionisation potential, electron affinity, electronegativity, chemical hardness and softness, global electrophilicity, and chemical potential of the titled compound. The examined compound's significant DFT features were compared with those of other compounds that have been previously reported. In compound DHDOBN strong electron-withdrawing –CN group present at the para position makes the titled compound kinetically more reactive. The small EHOMO and ELUMO energy gap due to cyano group makes it soft and more polarizable molecule. The DHDOBN compound was tested for antibacterial activity against two Gram-negative bacterial strains namely E. coli and P. Vulgaris and two Gram-positive bacterial strains namely S. aureus and B. subtilis, whereas fungal inhibitory action was tested against A. Niger and C. albicans. The DHDOBN compound was revealed to show moderate antibacterial and antifungal potential.