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Anion-/cation-directed reaction routes to polymorphic forms of a pyrazole-type ligand and its coordination compounds with zinc. Key structural differences between polymorphs’

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Abstract

Synthetic paths toward the two polymorphs of a monohydrate, one anhydrous polymorph of 1-carboxamidino-5-hydroxy-3-methylpyrazole (hcmp) and two polymorphs of zinc complexes containing hcmp ligand are presented. By choosing ions which are not part of the final product, it is possible to direct the synthesis toward the particular polymorph. In all three modifications of hcmp, the same hydrogen bonding motif appears, leading to formation of similar molecular chains. Differences arise due to different modes of chain aggregation and the presence of solvent water. Analysis of the crystal packing and the energetic features of hcmp polymorphs is made using the PIXEL model. The thermal decomposition processes are examined using differential scanning calorimetry and thermogravimetry. Analysis of crystal packing in the two polymorphs of zinc complex suggests the key role of the hydrogen bonding capacity of the aqua ligand for the appearance of the two polymorphic forms. In both polymorphs of zinc complex, stacking interactions have an important role. However, the enhanced hydrogen bonding capacity of the aqua ligand influences the formation of multistacking arrangement.

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Acknowledgments

This work was supported by the Ministry of Education and Science of the Republic of Serbia (continuation of the project No. 172014). The authors thank Dr Slađana B. Novaković for helpful discussions.

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Authors and Affiliations

  1. Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovica 3, Novi Sad, 21000, Serbia

    Berta Barta Holló & Katalin Mészáros Szécsényi

  2. Biological Research Centre HAS, Institute of Biophysics, Szeged, Hungary

    Mária Deli & Lóránd Kiss

  3. Laboratory of Plastics and Rubber Technology, Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, Műegyetem rakpart 3. H/1, Budapest, 1111, Hungary

    Alfréd Kállay-Menyhárd

  4. Research Center for Natural Sciences, Institute of Materials Science and Environmental Chemistry, Hungarian Academy of Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary

    Alfréd Kállay-Menyhárd

  5. Faculty of Chemistry, University of Belgrade, P.O. Box 51, Belgrade, 11158, Serbia

    Vukosava Živković-Radovanović

  6. Laboratory of Theoretical Physics and Condensed Matter Physics, VINČA’ Institute of Nuclear Sciences, University of Belgrade, P.O. Box 522, Belgrade, 11001, Serbia

    Zoran D. Tomić

Authors
  1. Berta Barta Holló
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  2. Katalin Mészáros Szécsényi
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  3. Mária Deli
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  7. Zoran D. Tomić
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Correspondence to Zoran D. Tomić.

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Barta Holló, B., Mészáros Szécsényi, K., Deli, M. et al. Anion-/cation-directed reaction routes to polymorphic forms of a pyrazole-type ligand and its coordination compounds with zinc. Key structural differences between polymorphs’. Struct Chem 27, 1121–1133 (2016). https://doi.org/10.1007/s11224-015-0734-1

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  • DOI: https://doi.org/10.1007/s11224-015-0734-1

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