Hydrogen-bonded assemblies in the molecular crystals of 2,2′-thiodiacetic acid with ethylenediamine and o-phenylenediamine
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- 作者：V. Gomathi and C. Theivarasu
- 关键词：hydrogen-bonded assemblies ; crystal structure ; 2 ; 2&prime ; -thiodiacetic acid ; o-phenylenediamine ; ethylenediamine
- 刊名：Acta Crystallographica Section C
- 出版年：2017
- 出版时间：February 2017
- 年：2017
- 卷：73
- 期：2
- 页码：97-103
- 全文大小：1053K
- ISSN：1600-5759
文摘
Carboxylate molecular crystals have been of interest due to the presence of hydrogen bonding, which plays a significant role in chemical and crystal engineering, as well as in supramolecular chemistry. Acid–base adducts possess hydrogen bonds which increase the thermal and mechanical stability of the crystal. 2,2′-Thiodiacetic acid (Tda) is a versatile ligand that has been widely explored, employing its multidendate and chelating coordination abilities with many metals; however, charge-transfer complexes of thiodiacetic acid have not been reported. Two salts, namely ethylenediaminium 2,2′-thiodiacetate, C2H10N22+·C4H4O4S22−, denoted Tdaen, and 2-aminoanilinium 2-(carboxymethylsulfanyl)acetate, C6H9N2+·C4H5O4S−, denoted Tdaophen, were synthesized and characterized by IR, 1H and 13C NMR spectroscopies, and single-crystal X-ray diffraction. In these salts, Tda reacts with the aliphatic (ethylenediamine) and aromatic (o-phenylenediamine) diamines, and deprotonates them to form anions with different valencies and different supramolecular networks. In Tdaen, the divalent Tda2− anions form one-dimensional linear supramolecular chains and these are extended into a three-dimensional sandwich-type supramolecular network by interaction with the ethylenediaminium cations. However, in Tdaophen, the monovalent Tda− anions form one-dimensional zigzag supramolecular chains, which are extended into a three-dimensional supramolecular network by interaction with the 2-aminoanilinium cations. Thus, both three-dimensional structures display different ring motifs. The structures of these diamines, which are influenced by hydrogen-bonded assemblies in the molecular crystals, are discussed in detail.