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Crystal Structures of Two Salts from Piperidine, Naphthalene-1,5-Disulfonic Acid, and 4-Nitrophthalic Acid

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Abstract

Two anhydrous salts of piperidine have been prepared with naphthalene-1,5-disulfonic acid, and 4-nitrophthalic acid by slow evaporation technique, and their structures were fully characterized. These two structures adopted homo or hetero supramolecular synthons. Compound 1 crystallizes in the triclinic, space group P-1, with a = 7.728(3) Å, b = 8.042(3) Å, c = 9.150(3) Å, α = 80.631(4)°, β = 79.433(4)°, γ = 86.531(4)°, V = 551.3(3) Å3, Z = 1. Compound 2 crystallizes in the monoclinic, space group P2(1)/c, with a = 6.3466(5) Å, b = 24.008(2) Å, c = 9.0390(7) Å, α = 90°, β = 97.0050(10)°, γ = 90°, V = 1367.01(19) Å3, Z = 4. Analysis of the crystal packing of 1, 2 suggests that there are N–H···O hydrogen bonds between the acids and the piperidine in both compounds. Except the classical hydrogen bonds, the secondary propagating interactions including CH2···O, O···Cπ, and CH2···π interactions also play important roles in structure extension. In conclusion, we have shown that 3D structures can be constructed by collective non-covalent interactions.

Graphical Abstract

The crystal structures of the salts from piperidine, naphthalene-1,5-disulfonic acid, and 4-nitrophthalic acid are predominantly stabilized by classical hydrogen bonds as well as CH2···O, O···Cπ, and CH2···π interactions.

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Acknowledgments

This research was supported by Zhejiang Provincial Natural Science Foundation of China under Grant No. LY14B010006, the Education Office Foundation of Zhejiang Province under Grant No. Y201017321, the National Training Programs of Innovation and Entrepreneurship of China for Undergraduates under Grant No. 201410341022, the Zhejiang A & F University Science Foundation under Grant No. 2009FK63, and the Open Foundation of Key Laboratory of Chemical Utilization of Forestry Biomass of Zhejiang Province, Zhejiang A & F University under Grant No. 2015CUFB02.

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Authors and Affiliations

  1. Jiyang College, Zhejiang A & F University, Zhu’Ji, 311800, People’s Republic of China

    Shouwen Jin & Chao Feng

  2. Key Laboratory of Chemical Utilization of Forestry Biomass of Zhejiang Province, Zhejiang A & F University, Lin’an, 311300, Zhejiang Province, People’s Republic of China

    Shouwen Jin, Chao Feng, Xianhong Wen & Daqi Wang

  3. Department of Chemistry, Liaocheng University, Liaocheng, 252059, People’s Republic of China

    Shouwen Jin, Chao Feng, Xianhong Wen & Daqi Wang

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  1. Shouwen Jin
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  2. Chao Feng
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  3. Xianhong Wen
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Correspondence to Shouwen Jin.

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Jin, S., Feng, C., Wen, X. et al. Crystal Structures of Two Salts from Piperidine, Naphthalene-1,5-Disulfonic Acid, and 4-Nitrophthalic Acid. J Chem Crystallogr 46, 21–27 (2016). https://doi.org/10.1007/s10870-015-0623-x

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