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Synthesis and Characterization of N,N’-terephthalidenebis(o-aminoaniline): Crystal Structures of Its Two Polymorphic Forms Controlled by Changing the Crystallization Solvent

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Abstract

The compound N,N’-terephthalidenebis(o-aminoaniline) (1) was synthesized by the condensation reaction of terephthalaldehyde with o-phenylenediamine and structurally characterized by 1H NMR, 13C NMR, FT-IR, mass spectrometry, elemental analysis and single crystal X-ray diffraction. The structures of two distinct polymorphic forms of N,N’-terephthalidenebis(o-aminoaniline) (1), have been studied using single crystals obtained under different crystallizing conditions. Similarities in molecular conformation and detailed differences in arrangements of these molecules in crystal lattice are distinguished between two polymorphs of (1) and discussed.

Graphical Abstract

The structures of two distinct polymorphic forms of N,N’-terephthalidenebis(o-aminoaniline) (1), have been studied using single crystals obtained under different crystallizing conditions.

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Acknowledgments

Marek Dzięgielewski was the participant of the project entitled “Doktoranci—Regionalna Inwestycja w Młodych naukowców—Akronim D-RIM”, which is co-financed by the EU from the European Social Fund in the framework of the Operational Programme Human Capital, Priority VIII, Subaction 8.2.1. and wishes to thank for the scholarship. The X-ray measurements were carried out within the Project I-20110099 EC at the light source DORIS III at HASYLAB/DESY, Hamburg, Germany. The research leading to these results has received funding from the European Community’s Seventh Framework Programme (FP7/2007–2013) under Grant agreement No. 312284. Dr. Carsten Paulmann is gratefully acknowledged for his helpful assistance during X-ray measurements. Authors also would like to thank Mr. Mateusz Irzykowski for preparing numerous crystallizations.

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Authors and Affiliations

  1. Structural Chemistry and Crystallography Group, Faculty of Chemistry, University of Łódź, Pomorska 163/165, 90-236, Łódź, Poland

    Lilianna Chęcińska & Magdalena Małecka

  2. Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403, Łódź, Poland

    Jarosław Lewkowski & Marek Dzięgielewski

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  1. Lilianna Chęcińska
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  2. Jarosław Lewkowski
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  3. Magdalena Małecka
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  4. Marek Dzięgielewski
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Correspondence to Jarosław Lewkowski.

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Chęcińska, L., Lewkowski, J., Małecka, M. et al. Synthesis and Characterization of N,N’-terephthalidenebis(o-aminoaniline): Crystal Structures of Its Two Polymorphic Forms Controlled by Changing the Crystallization Solvent. J Chem Crystallogr 43, 421–428 (2013). https://doi.org/10.1007/s10870-013-0439-5

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