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Cu(II), Ni(II) and Fe(II) complexes with a new substituted [1,2,4] triazole Schiff base derived from 4-amino-5-(thien-2-yl ethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and 2-hydroxy-1-naphthaldehyde: synthesis, characterization and a comparison of theoretical and experimental results by Ab inito calculation

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Abstract

The synthesis and structural properties of two novel compounds, 4-amino-5-(thien-2-yl ethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and 4-{[(2-hydroxy-1-naphthyl)methyl-ene]amino}-5-(thien-2-ylmethyl) − 2,4-dihydro-3H-1,2,4-triazol-3-one have been described. 4-Amino-5-(thien-2-ylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one was synthesized by treating N-propionyl-2-thien-2-ylethane-hydrazonoate with hydrazine hydrate and the Schiff base was obtained from condensation of substituted amine with 2-hydroxy-1-naphthaldehyde. The Cu(II), Ni(II) and Fe(II) complexes were prepared and characterized by elemental analyses, IR, magnetic moment, UV–Vis, mass spectral data and 1H- and 13C-NMR IR spectra. The Schiff base is coordinated to the metal ions in a tridentate manner with OON donors of the phenolic O, carbonyl O and triazolic N. From the magnetic and UV spectral data, it was found the geometrical structure of Cu(II) and Fe(II) ions are octahedral while Ni(II) ion is square planar.Ab-inito 6-31 G* level calculations provided structural information and IR data that were in good agreement with experimental results.

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Authors and Affiliations

  1. Department of Chemistry, Karadeniz Technical University, 61080, Trabzon, Turkey

    Kemal Sancak, Mustafa Er, Yasemin Ünver, Melike Yildirim & Ismail Degirmencioglu

  2. Department of Chemistry, Karadeniz Technical University, Rize Faculty of Arts and Sciences, 53100, Rize, Turkey

    Kerim Serbest

Authors
  1. Kemal Sancak
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  2. Mustafa Er
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  3. Yasemin Ünver
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  4. Melike Yildirim
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  5. Ismail Degirmencioglu
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  6. Kerim Serbest
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Correspondence to Ismail Degirmencioglu.

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Sancak, K., Er, M., Ünver, Y. et al. Cu(II), Ni(II) and Fe(II) complexes with a new substituted [1,2,4] triazole Schiff base derived from 4-amino-5-(thien-2-yl ethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one and 2-hydroxy-1-naphthaldehyde: synthesis, characterization and a comparison of theoretical and experimental results by Ab inito calculation. Transition Met Chem 32, 16–22 (2007). https://doi.org/10.1007/s11243-006-0122-1

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