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Spectroscopic studies, antimicrobial activities, and crystal structure of N-[2-hydroxy-1-naphthylidene]3, 5-bis(trifluoromethyl)aniline

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A new Schiff base compound has been synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 3,5-bis(trifluoromethyl)aniline.The title compound was characterized by elemental analysis, IR,1H NMR,13C NMR, and UV–Visible techniques.Its UV–Vis spectra was examined in polar and nonpolar solvents and in acidic and basic media. The crystal structure of the compound showed the OH group to be ortho to the imine group. It crystallizes in the monoclinic space group P21 with a = 11.328(2), b = 6.125(1), c = 11.937(2) Å, V = 825.1(2) Å3, D x = 1.543 g cm−3and Z = 2. An intramolecular O1- H⋯N1 [2.558(7) Å] hydrogen bond stabilizes the molecule. The compound has also been characterized by its antimicrobial activities. The ligand has been screened in vitro against the organisms Escherichia coli ATCC 11230, Staphylococcus aureus ATCC 6538, Klebsiella pneumoniae UC57, Micrococcus luteus La 2971, Proteus vulgaris ATCC 8427, Pseudomonas aeruginosa ATCC 27853, Mycobacterium smegmatis CCM 2067, Bacillus cereus ATCC 7064, and Listeria monocytogenes ATCC 15313, the yeast cultures Candida albicans ATCC 10231, Kluyveromyces fragilis NRRL 2415, Rhodotorula rubra DSM 70403, Debaryomyces hansenii DSM 70238, and Hanseniaspora guilliermondii DSM 3432.

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Authors and Affiliations

  1. Department of Physics, Faculty of Science, Ankara University, TR-06100, Beşevler-Ankara, Turkey

    Hüseyin Ünver & Tahsin Nuri Durlu

  2. Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, TR-17100, Çanakkale, Turkey

    Mustafa Yıldız

  3. Department of Natural Sciences, Faculty of Education, Çanakkale Onsekiz Mart University, TR-17100, Çanakkale, Turkey

    Aşkın Kiraz

  4. Department of Physics, Faculty of Science and Arts, Ondokuz Mayıs University, TR-55139, Kurupelit, Turkey

    Nazan Ocak İskeleli & Ahmet Erdönmez

  5. Department of Biology, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, TR-17100, Çanakkale, Turkey

    Başaran Dülger

  6. Department of Physics, Faculty of Arts and Sciences, Kırıkkale University, Yahşihan Campus, TR-71450, Kırıkkale, Turkey

    Tahsin Nuri Durlu

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  1. Hüseyin Ünver
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  2. Mustafa Yıldız
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Correspondence to Mustafa Yıldız.

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Ünver, H., Yıldız, M., Kiraz, A. et al. Spectroscopic studies, antimicrobial activities, and crystal structure of N-[2-hydroxy-1-naphthylidene]3, 5-bis(trifluoromethyl)aniline. J Chem Crystallogr 36, 229–237 (2006). https://doi.org/10.1007/s10870-005-9053-5

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