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

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2022-03, Vol.78 (3), p.201-211
• Main Authors: Çakmak, Şükriye, Koşar Kırca, Başak, Veyisoğlu, Aysel, Yakan, Hasan, Ersanlı, Cem Cüneyt, Kütük, Halil
• Format: Article
• Language: English
• Subjects: Antiinfectives and antibacterials; antimicrobial activity; Antimicrobial agents; Bacteria; Biological activity; carboxamide; Chemical analysis; Chemical bonds; Chemical synthesis; Crystal structure; Crystallization; Crystallography, X-Ray; Density functional theory; Electronics; furan; Furans - pharmacology; Hirshfeld surface; Hydrogen Bonding; Infrared analysis; Infrared spectroscopy; Investigations; Magnetic Resonance Spectroscopy; Microorganisms; NMR spectroscopy; Optical properties; spectroscopic evaluation; Spectroscopy, Fourier Transform Infrared; Surface analysis (chemical); thiazolamide; Thiazoles - chemistry; Thiazoles - pharmacology; X-ray diffraction; XRD
• ISSN: 2053-2296; 0108-2701; 2053-2296; 1600-5759
• DOI: 10.1107/S2053229622002066

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. A thiazole‐based heterocyclic amide, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, was synthesized and investigated for its antimicrobial activity against eight microorganisms and showed good activity against all eight microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.