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Supramolecular Organic Salts Constructed from 6-Hydroxyquinoline and Nitrobenzoic Acids

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Abstract

The crystal structures of the proton-transfer salts of 6-hydroxyquinoline with 3,5-dinitrobenzoic acid (1) and 4-nitrobenzoic acid (2) have been determined at room temperature. Their comparative structural features and hydrogen-bonding patterns are described here. Compound 1 crystallizes in the monoclinic P21/c space group, while 2 in the triclinic P−1 space group. Unit cell dimensions and contents are: a = 7.6956(15), b = 26.075(5), c = 7.7233(15) Å, β = 95.96(3)° for 1; a = 7.7325(15), b = 8.5939(17), c = 12.394(3) Å, β = 77.63(3)° for 2. Supramolecular architectures are formed by intermolecular hydrogen bonds in the proton-transfer process. The supramolecular structures are stabilized by N–H···O, O–H···O and C–H···O hydrogen bonds between the two components. Extensive hydrogen-bonding interactions give two-dimensional network structures. In addition, π–π stacking interactions exist in the salt 1 due to the aromatic rings.

Graphical Abstract

The crystal structures of the proton-transfer salts of 6-hydroxyquinoline with 3,5-dinitrobenzoic acid (1) and 4-nitrobenzoic acid (2) have been determined at room temperature. The supramolecular structures are stabilized by N–H···O, O–H···O and C–H···O hydrogen bonds between the two components. In addition, π–π stacking interactions exist in the salt 1 due to the aromatic rings.

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Acknowledgments

This work was supported by Nanjing University of Posts and Telecommunications (NY211027 and NY211135), the Natural Science Foundations of China (Grant 20901016) and the National Basic Research Program of China (Grant 2009CB930601).

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Authors and Affiliations

  1. Key Laboratory for Organic Electronics & Information Displays (KLOEID) and Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications, 9 Wenyuan Road, Nanjing, 210046, China

    Yong-Hua Li, Xue-Hua Ding & Wei Huang

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  1. Yong-Hua Li
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  2. Xue-Hua Ding
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  3. Wei Huang
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Correspondence to Yong-Hua Li.

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Li, YH., Ding, XH. & Huang, W. Supramolecular Organic Salts Constructed from 6-Hydroxyquinoline and Nitrobenzoic Acids. J Chem Crystallogr 42, 905–910 (2012). https://doi.org/10.1007/s10870-012-0335-4

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