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Open AccessArticle

X-ray Crystal Structure, Geometric Isomerism, and Antimicrobial Activity of New Copper(II) Carboxylate Complexes with Imidazole Derivatives

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National Institute of Materials Physics, 405A Atomistilor, 077125 Magurele-Bucharest, Romania
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National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donat Avenue, 400293 Cluj-Napoca, Romania
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Department of Soil Sciences, University of Agronomical Sciences and Veterinary Medicine, 59 Mărăşti Str., Sector 1, 011464 Bucharest, Romania
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Department of Microbiology, Faculty of Biology, University of Bucharest, 1–3 Aleea Portocalelor Str., 60101 Bucharest, Romania
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Life, Environment and Earth Sciences Division, Research Institute of the University of Bucharest (ICUB), Spl. Independentei 91–95, 010271 Bucharest, Romania
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3S-Pharmacological Consultation & Research GmbH, 1 Koenigsbergerstrasse, 27243 Harpstedt, Germany
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Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany
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Department of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 90–92 Panduri Str., 050663 Bucharest, Romania
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3253; https://doi.org/10.3390/molecules23123253
Received: 1 November 2018 / Revised: 5 December 2018 / Accepted: 5 December 2018 / Published: 9 December 2018
(This article belongs to the Section Inorganic Chemistry)
Five new copper(II) acrylate complexes (acr is the acrylate anion: C3H3O2) with imidazole derivatives (2-methylimidazole/2-MeIm, 5-methylimidazole/5-MeIm, 2-ethylimidazole/2-EtIm) of type: cis-[Cu(2-RIm)2(acr)2]·xH2O ((1): R = –CH3, x = 2; (4): R = –CH2–CH3, x = 0), trans-[Cu(2-RIm)2(acr)2] ((2): R = –CH3; (5): R = –CH2–CH3) and trans-[Cu(5-RIm)2(acr)2] ((3): R = –CH3) have been prepared and characterized by elemental analysis, Fourier Transform Infrared spectrometry (FTIR), Electron Paramagnetic Resonance (EPR), electronic reflectance spectroscopy, scanning electron microscopy, and mass spectrometry. The single crystal X-ray diffraction study of complexes (2) and (5) reveals that the copper(II) ion is located on an inversion center and show elongated octahedral geometry completed by two coplanar bidentate acrylates and two unidentate imidazole derivatives displayed in trans positions. For complex (4) the single crystal X-ray diffraction shows that the copper(II) ion is in a distorted octahedral environment which can be easily confused with a trigonal prism completed by two bidentate acrylates and two unidentate imidazole derivatives displayed in cis positions. These results indicate the fact that complexes (4) and (5) are the geometric isomers of the same compound bis(acrylate)-bis(2-ethylimidazole)-copper(II). Complexes (1) and (2), as well as (4) and (5), were produced simultaneously in the reaction of the corresponding copper(II) acrylate with imidazole derivatives in methanol solution. Furthermore, in order to be able to formulate potential applications of the obtained compounds, our next goal was to investigate the in vitro antimicrobial activity of the synthesized complexes against Gram-positive and Gram-negative bacteria, as well as fungal strains, of both clinical and ecological importance (biodeterioration of historical buildings). The trans isomers (2) and (5), followed by (4) have shown the broadest range of antimicrobial activity. In case of (1) and (2) isomers, the trans isomer (2) was significantly more active than cis (1), while the cis isomer (4) proved to be more active than trans (5). Taken together, the biological evaluation results indicate that the trans (2) was the most active complex, demonstrating its potential for the development of novel antimicrobial agents, with potential applications in the biomedical and restoration of architectural monuments fields. View Full-Text
Keywords: X-ray structure; geometric isomerism; copper(II) complex; imidazole derivative; antimicrobial activity X-ray structure; geometric isomerism; copper(II) complex; imidazole derivative; antimicrobial activity
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Vlaicu, I.D.; Borodi, G.; Scăețeanu, G.V.; Chifiriuc, M.C.; Măruțescu, L.; Popa, M.; Stefan, M.; Mercioniu, I.F.; Maurer, M.; Daniliuc, C.G.; Olar, R.; Badea, M. X-ray Crystal Structure, Geometric Isomerism, and Antimicrobial Activity of New Copper(II) Carboxylate Complexes with Imidazole Derivatives. Molecules 2018, 23, 3253.

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