Synthesis, antibacterial and computational studies of Halo Chalcone hybrids from 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one

Three chalcones with a 2,3‐dihydrobenzofuran linkage were analyzed by applying the density functional theory (DFT) and B3LYP approach with the 6‐311G(d,p) basis set in this report. Spectroscopic and theoretical analyses were used to examine the structures of these three chalcones. The chalcone molecules' HOMO‐LUMO energy was determined. Chemical reactivity parameters and molecular electrostatic surface potential (MESP) plots were obtained to gain useful insight into the distribution of charge density. The HOMO–LUMO gap of all three chalcones were calculated and discussed. The (E)‐3‐(2,3‐dihydrobenzofuran‐5‐yl)‐1‐phenylprop‐2‐en‐1‐one (DBPP) is discussed in detailed for the theoretical and experimental correlation. The captodative phenomenon appears to be the most polar molecule, with a dipole moment of 8.53 Debye. The decreased bandgap indicates that charge transfer occurs within the DBNPP molecule. When the solvent polarity is changed to DCM and DMSO from the gas phase, there is an event of a hyperchromic shift. The C19 carbon atom has the highest negative atomic charge while C21 is the carbon with the largest positive charge. From the MESP plots, we can conclude that the most electropositive region is located over the hydrogen atoms of the five‐membered ring, and the electronegative region is located over the oxygen atoms. Time‐dependent density functional theory (TD‐DFT) using B3LYP functional with 6‐311G(d,p) as basis set were used for the electronic absorption study in gas phase, dichloromethane and dimethyl sulfoxide. The UV‐Vis absorption peaks and fundamental vibrational wavenumbers were calculated and a good agreement between observed and theoretical results has been achieved.

“…have been studied to explore molecular structure, HOMO‐LUMO and spectroscopic properties using DFT studies. [ 23‐33 ]…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DFT calculations on three 2,3‐dihydrobenzofuran linked chalcones: Structural, HOMO‐LUMO and spectroscopic (UV‐Vis and IR) interpretation

Adole

2023

Antimicrobial and computational investigation of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone motifs

Shinde,

Adole,

Jagdale

2021

In this work, we report the anti‐microbial and computational study of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone scaffolds. The (E)‐2‐(4‐(trifluoromethyl)benzylidene)‐2,3‐dihydro‐1H‐inden‐1‐one (TFMBD‐1) and (E)‐2‐(4‐(trifluoromethoxy)benzylidene)‐2,3‐dihydro‐1H‐inden‐1‐one (TFMBD‐2) were synthesized by Claisen‐Schmidt reaction. The in‐depth structural analysis of optimized molecular structures, bond lengths and bond angles has been discussed by using density functional theory (DFT) with B3LYP/6‐311++G(d,p) basis set. The geometrical parameters, frontier molecular orbitals, global reactivity parameters, and MESP surfaces were all predicted using the same basis set on completely optimized geometries. Ionization potential, electron affinity, electronegativity, chemical hardness, global softness, global electrophilicity, and chemical potential were calculated using HOMO and LUMO energy values. Besides, the synthesized compounds were screened for their in‐vitro antibacterial and antifungal study. Antibacterial activity was screened against two Gram‐negative bacteria, E. coli and P. vulgaris, as well as against two Gram‐positive bacteria, S. aureus and B. subtilis, and antifungal activity was evaluated against A. niger and C. albicans. The TFMBD‐1 was revealed to be a more effective antibacterial and antifungal agent than TFMBD‐2.

Spectroscopic (FTIR and UV), quantum Chemical, antifungal and antioxidant investigations of (E)‐7‐(4‐(trifluoromethyl)benzylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one: A combined experimental and theoretical study

Adole¹,

Shinde³

et al. 2021

In the current study, we report the antifungal, antioxidant, and computational study of (E)‐7‐(4‐(trifluoromethyl)benzylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one (FMBIF). The structure of the FMBIF was confirmed using spectroscopic techniques such as UV‐Vis, FT‐IR, 1H NMR, 13C NMR, and HRMS. Antifungal activity of the FMBIF was evaluated against four fungal strains namely Rhizopus oryzae, Mucor mucido, Aspergillus niger, and Candida albicans. The FMBIF was found to exhibit a good spectrum of antifungal activity against all the tested fungal strains. Additionally, it was also revealed to show good antioxidant potential. The Gaussian‐03 package was used to perform the density functional theory (DFT) calculations. The structural, chemical, UV‐Vis, and vibrational characteristics were evaluated using the DFT/B3LYP approach with a 6‐311++G(d,p) basis set. Using optimized molecular structure, the absorption wavelength, excitation energy, force strength, and electronic transitions were calculated using the TD‐DFT method with the CAM‐B3LYP functional and 6‐311++G(d,p) basis set. Mulliken atomic charges and molecular electrostatic potential surfaces are explored to investigate the electron density distribution in the titled compound. The DFT investigation's spectroscopic results were in good concurrence with experimental data.