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Piperazinium Bis(hydrogen-3,5-pyrazoledicarboxylate) Proton Transfer Compound and Its Zinc(II) Complex: Synthesis, Characterization and Crystal Structure

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Abstract

Two compounds including a proton transfer ion pair, (pipzH2)(pdcH)2·2H2O (1) (where pipz: piperazine and pdcH2: pyrazole-3,5-dicarboxylic acid) and its Zn(II) complex (2), (pipzH2)[Zn(pdc)2(H2O)2]·6H2O, were synthesized and characterized using elemental analysis, IR spectroscopy and single crystal X-ray diffraction methods. The compound 1 crystallizes in the triclinic space group P\(\bar {1}\) with Z = 2. The unit cell dimensions are: a = 6.886(3) Å, b = 8.132(3) Å, c = 8.902(3) Å, α = 94.707(9)°, β = 99.632(9)°, γ = 111.508(8)°. The crystal system of 2 is monoclinic with space group P21/c and has two molecules per unit cell. The unit cell dimensions are: a = 12.050(2) Å, b = 13.163(2) Å, c = 7.610(1) Å, β = 97.610(4)°. The zinc(II) atom has a distorted octahedral coordination geometry. The two pdc2− units are almost coplanar to each other. In both crystal structures, a wide range of noncovalent interactions including hydrogen bonding (types of O–H⋯O, N–H⋯O and C–H⋯O), π–π stacking and ion pairing connect the various components into supramolecular structures.

Graphical Abstract

X-ray crystal structure of the novel 1:2 proton transfer compound, (pipzH2)(pdcH)2·2H2O (where pipz: piperazine and pdcH2: pyrazole-3,5-dicarboxylic acid) and its Zn(II) complex, (pipzH2)[Zn(pdc)2(H2O)2]·6H2O, show intermolecular N–H⋯O, O–H⋯O and C–H⋯O hydrogen bonds and π–π stacking, together with ion pairing, are responsible for extending the structure in three dimensions, resulting in a supramolecular network.

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Acknowledgements

The authors greatly acknowledge the financial and scientific support from the Qom Branch, Islamic Azad University, to the first author in this study. This paper is a part of a project entitled “Synthesis and characterized of new ligands containing pyrazol-3,5-dicarboxylic acid and benzene-1,2,4,5-tetracarboxylic acid and the study of their metal coordination”.

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Authors and Affiliations

  1. Department of Chemistry, Qom Branch, Islamic Azad University, Qom, Iran

    Mahboubeh A. Sharif & Gholam Reza Najafi

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  1. Mahboubeh A. Sharif
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  2. Gholam Reza Najafi
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Correspondence to Mahboubeh A. Sharif.

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Sharif, M.A., Najafi, G.R. Piperazinium Bis(hydrogen-3,5-pyrazoledicarboxylate) Proton Transfer Compound and Its Zinc(II) Complex: Synthesis, Characterization and Crystal Structure. J Chem Crystallogr 49, 98–105 (2019). https://doi.org/10.1007/s10870-018-0741-3

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  • DOI: https://doi.org/10.1007/s10870-018-0741-3

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