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Hydrogen-bonding directed cocrystallization of flexible piperazine with hydroxybenzoic acid derivatives: Structural diversity and synthon prediction

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Abstract

Four hydroxybenzoic acid building blocks, m-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxyterephthalic acid, and 5-hydroxyisophthalic acid, have been synthesized as robust cocrystallizing agents and employed in reactions with piperazine, including [(C4H12N 2+2 )·(C7H5O −3 )2] (1), [(C4H12N 2+2 )·(C7H5O4/−)2] (2), [(C4H12N 2+2 )·(C8H5O 2−6 )] (3), and [(C4H12N 2+2 )1/2·(C8H5O −5 )]·2H2O (4). Hydrogen-bonded directed assemblies of four salts were validated by single-crystal X-ray diffraction analysis. In compounds 1–4, hydroxybenzoic acids are all deprotonated and piperazine molecules are all protonated to form piperazine dications and keep the chair conformation. Thermal stability of these compounds has been investigated.

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Authors and Affiliations

  1. State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, China

    Lei Wang, XiFeng Lu & XuTang Tao

  2. Key Laboratory of Eco-chemical Engineering, Ministry of Education; College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Lei Wang, RuiFeng Xue, LingYan Xu & RuiXin Chen

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  1. Lei Wang
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  2. RuiFeng Xue
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  3. LingYan Xu
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  4. XiFeng Lu
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Correspondence to XuTang Tao.

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Wang, L., Xue, R., Xu, L. et al. Hydrogen-bonding directed cocrystallization of flexible piperazine with hydroxybenzoic acid derivatives: Structural diversity and synthon prediction. Sci. China Chem. 55, 1228–1235 (2012). https://doi.org/10.1007/s11426-011-4487-4

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  • DOI: https://doi.org/10.1007/s11426-011-4487-4

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