Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity

Abstract

A thiazole-based heterocyclic amide, namely, N-(thiazol-2-yl)furan-2-carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single-crystal X-ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P21/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second-order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram-negative bacteria, Gram-positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.

Synthesis, XRD/HSA‐Interactions, QTAIM Analysis, Optical and Nonlinear Optical Responses Studies of Cu(II) Complex with the Schiff Base Ligand Derived from 5‐Bromosalicylaldehyde

“…Hirshfeld surface analysis yields valuable information on the quantitative ratios of atom … atom short contacts with the ability to establish weak hydrogen bond intermolecular interactions, as well as the locations of these interactions [48] . Crystal Explorer2.1( was used to visualize and quantify the differences and similarities of intermolecular interactions throughout the crystal structures of [Cu L(CH 3 COO)] [49] …”

“…[48] Crystal Explorer2.1( was used to visualize and quantify the differences and similarities of intermolecular interactions throughout the crystal structures of [Cu L(CH 3 COO)]. [49] The Hirshfeld surface plotted over d norm can be used to highlight strong H-bonding as well as H-bonding interactions by utilizing different colors. This surface has three colors: red, white, and blue.…”

Synthesis, Spectroscopic Characterization, Single-Crystal Structure, Hirshfeld Surface Analysis, and Antimicrobial Studies of 3-Acetoxy-2-methylbenzoic Anhydride

“…The Hirshfeld surface was analyzed with CrystalExplorer21 to identify various intermolecular contacts in the crystal structure. − The analysis of the 3D Hirshfeld surface (HS) and 2D fingerprint plots (FPs) were performed in order to describe the molecular structure of AMA. The surfaces mapped over d norm , shape index, and curvedness were shown in Figure .…”

Synthesis of a New DPTYEAP Ligand and Its Complexes with Their Assessments on Physical Properties, Antioxidant, and Biological Potential to Treat Breast Cancer

“…The 13 C-NMR Spectrum of the ligand DPTYEAP exhibited a signal at 40.311 ppm, due to DMSO. The carbon C 23 containing the group OH gave a signal at 136.648 ppm [21], while the carbon C 9 gave the signal at 116.476 ppm due to thiazole [22]. Where the following carbon atoms C 3 -C 4 -C 10 -C 22 gave values between 129.092-131.752 ppm due to the connection of carbon atoms with nitrogen atoms [23][24].…”