Crystalline pyrazine-2-amidoxime isolated by diffusion method and its structural and behavioral analysis in the context of crystal engineering and microbiological activity. Issue 69 (7th July 2016)

• Record Type: Journal Article
• Authors: Chylewska, Agnieszka; Ogryzek, Małgorzata; Głębocka, Angelika; Sikorski, Artur; Turecka, Katarzyna; Raczyńska, Ewa. D.; Makowski, Mariusz
• Is Part Of: RSC advances. Volume 6:Issue 69(2016)
• Page Start: 64499
• Page End: 64512
• Publication Date: 2016-07-07
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra10537h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The physicochemical characterizations ofPAOX were obtained both in solid-state and solution, and its two anti-conformers were observed in the X-ray. Its antimicrobial properties were tested against reference strains of bacteria and yeast. Abstract : Pyrazine-2-amidoxime (PAOX ) is a structural analogue of a popular drug, i.e. pyrazine-2-carboxamide (PZA ). The crystallinePAOX was obtained by diffusion as a method of crystallization. Various types of intermolecular interactions between the H-bond donors (CH, NH, and OH) and H-bond acceptors (hydroxyl O, imino N, aza N) were found betweenPAOX molecules in X-ray diffraction studies. It was observed in the crystal structure thatPAOX forms not only dimers but also stable helical-like polymers, stabilized by intermolecular interactions between two neighbouring molecules. Their geometric, energetic and spectroscopic properties were also characterised by DFT methods. Thermal decomposition ofPAOX was examined with the use of a TG-IR analysis (20–1000 °C), and the results were further resolved. Electrochemical behaviour of the compound studied in acetonitrile in the absence or presence of methanol was described in detail, and mechanisms of the anodic oxidation and cathodic reduction were proposed. The complexometric properties ofPAOX were examined against selected d-block metal ions in acetonitrile, as well as in aqueous solution. Biological assay ofPAOX was performed to determine the antimicrobial activity and potential pharmaceutical applications. The minimum inhibitory (MIC) and minimal bactericidal (or fungicidal) concentrations (MBC/MFC) forPAOX were determined against six microorganisms.