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Syntheses and Crystal Structures of Three Pyrrole-2-Carboxylate with C3-Symmetry

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Abstract

The reaction of three equivalents of 2-(trifluoroacetyl)pyrrole with triols [RC(CH2OH)3, R=H, CH3, CH2OH] produce triesters of pyrrole-2-carboxylic acid (1–3, respectively) which crystallize in space groups with molecular C3 symmetry coinciding with the crystallographic symmetry (averaged in the case of R=CH2OH). All are unsolvated. Compound 1 crystallizes in space group P-3 and 2 and 3 in space group P-43n. In all three, molecules form three R22(10) Hydrogen-bonded interactions between syn pyrrole N-H and carboxyl C = O on neighboring molecules. In 1, molecules are linked into infinite chains and hexamolecular rings, and the cavity at the center of the rings (site symmetry − 3) is too small to harbor a guest molecule. In 2 and 3, supramolecular assemblies radiate from four molecules with methyl and hydroxymethyl groups at tetrahedral sites in the cubic structures. Computations confirm the importance of Hydrogen-bonding in these assemblies which add to the hundreds of similar pyrrole carboxylates previously described.

Graphic Abstract

Applications of the R22(10) hydrogen bond motif formed between two pyrrole-2-carboxylate moieties in the design of hydrogen bonded framework. Three tripodal pyrrole-2-carboxylate compounds were synthesized, and their structure were characterized by X-ray crystallography. The three compounds self-assembled into hexamer or cubic supramolecular structures. The relibility of the motif was also proved by DFT calculations and search in Cambridge Structural Database (CSD).

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Acknowledgements

We sincerely thank the financial supports from the Natural Science Foundation of China (NSFC No. 21172174). We are indebted to Dr. Kun Liu, Department of Chemistry, Tianjin Normal University, for calculation.

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  1. College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecule, Tianjin Normal University, 300387, Tianjin, China

    Xiaoxue Liu & Zhenming Yin

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  1. Xiaoxue Liu
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  2. Zhenming Yin
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Correspondence to Zhenming Yin.

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Liu, X., Yin, Z. Syntheses and Crystal Structures of Three Pyrrole-2-Carboxylate with C3-Symmetry. J Chem Crystallogr 52, 105–112 (2022). https://doi.org/10.1007/s10870-021-00894-1

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  • DOI: https://doi.org/10.1007/s10870-021-00894-1

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