Crystalline pyrazine-2-amidoxime isolated by diffusion method and its structural and behavioral analysis in the context of crystal engineering and microbiological activity

Agnieszka Chylewska , Małgorzata Ogryzek , Angelika Głębocka , Artur Sikorski , Katarzyna Turecka , Ewa D. Raczyńska , Mariusz Makowski


Pyrazine-2-amidoxime (PAOX) is a structural analogue of a popular drug, i.e. pyrazine-2-carboxamide (PZA). The crystalline PAOX 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 between PAOX molecules in X-ray diffraction studies. It was observed in the crystal structure that PAOX 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 of PAOX 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 of PAOX were examined against selected d-block metal ions in acetonitrile, as well as in aqueous solution. Biological assay of PAOX was performed to determine the antimicrobial activity and potential pharmaceutical applications. The minimum inhibitory (MIC) and minimal bactericidal (or fungicidal) concentrations (MBC/MFC) for PAOX were determined against six microorganisms.
Author Agnieszka Chylewska (FCh / DGICh / LII)
Agnieszka Chylewska,,
- Laboratory of Intermolecular Interactions
, Małgorzata Ogryzek (FCh / DGICh / LII)
Małgorzata Ogryzek,,
- Laboratory of Intermolecular Interactions
, Angelika Głębocka (FCh / DGICh / LII)
Angelika Głębocka,,
- Laboratory of Intermolecular Interactions
, Artur Sikorski (FCh / DPCh / PK)
Artur Sikorski,,
- Pracownia Krystalochemii
, Katarzyna Turecka - [Gdanski Uniwersytet Medyczny]
Katarzyna Turecka,,
- Gdanski Uniwersytet Medyczny
, Ewa D. Raczyńska - [Szkoła Główna Gospodarstwa Wiejskiego]
Ewa D. Raczyńska,,
, Mariusz Makowski (FCh / DGICh / LII)
Mariusz Makowski,,
- Laboratory of Intermolecular Interactions
Journal seriesRSC Advances, ISSN 2046-2069, (A 30 pkt)
Issue year2016
Publication size in sheets0.65
ASJC Classification1500 General Chemical Engineering; 1600 General Chemistry
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa - Użycie Niekomercyjne (CC-BY-NC); with publication
Score (nominal)35
ScoreMinisterial score = 30.0, 18-03-2019, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 18-03-2019, ArticleFromJournal
Publication indicators WoS Citations = 1; Scopus Citations = 1; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 0.736; WoS Impact Factor: 2016 = 3.108 (2) - 2016=3.257 (5)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.