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Synthesis, Crystal Structure and Thermal Properties of N-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline

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Abstract

Two novel ferrocenyl substituted N-acetyl-2-pyrazolines, N-acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline (3) and N-acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline (4), have been synthesized and characterized by FTIR, 1H-NMR, 13C-NMR techniques, elemental analysis and X-ray structure analysis. Thermal properties of these compounds have been determined by TGA, DTA and DSC analysis. Compound 3 (C19H18N2O2Fe) crystallizes in the monoclinic space group P21/c and Z = 4, with a = 8.6970(4) Å, b = 18.4725(9) Å, c = 11.0041(5) Å, β = 110.942(3)°. Compound 4 (C19H18N2OSFe) crystallizes in the orthorhombic space group Fdd2 and Z = 16, with a = 84.242(2) Å, b = 13.5416(5) Å, c = 5.9405(2) Å, β = 90°. In terms of crystal packing, each compound shows different molecular arrangement, which are stabilized by C–H···O intermolecular weak hydrogen bonds, and/or C–H···π interactions.

Index Abstract

Two novel ferrocenyl-containing 2-pyrazolines have been synthesized and fully characterized by FT-IR, 1H-NMR, 13C-NMR techniques, elemental analysis and X-ray crystal structure analysis. Thermal properties of these compounds have been determined by TGA, DTA and DSC analysis.

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Acknowledgments

The authors acknowledge the Research Board Akdeniz University (grand no BAP-2007.01.0105.001) for financial support, the Faculty of Arts and Sciences Ondokuz Mayıs University, for the Stoe IPDS-II diffractometer (purchased under grand F.279 of the University Research Fund) and the Faculty of Arts and Sciences Gaziosmanpasa University, for the Thermal and NMR analyses.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Akdeniz University, Antalya, Turkey

    Günseli Turgut Cin, Seda Demirel Topel & Abban Cakıcı

  2. Department of Physics, Faculty of Art and Sciences, Giresun University, Giresun, Turkey

    Arzu Özek Yıldırım

  3. Department of Chemistry, Faculty of Art and Sciences, Gaziosmanpaşa University, Tokat, Turkey

    Ahmet Karadağ

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  1. Günseli Turgut Cin
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Correspondence to Günseli Turgut Cin.

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Cin, G.T., Demirel Topel, S., Cakıcı, A. et al. Synthesis, Crystal Structure and Thermal Properties of N-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline. J Chem Crystallogr 42, 372–380 (2012). https://doi.org/10.1007/s10870-011-0256-7

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