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Crystal and Molecular Structures of Four Salts from Isopropylamine, Cinnamic Acid, 2-Hydroxy-5-(phenyldiazenyl)benzoic Acid, m-Phthalic Acid and 2,6-Pyridinedicarboxylic Acid

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Abstract

Four isopropylamine derived supramolecular salts were synthesized and characterized by X-ray crystallography, IR, mp, and elemental analysis. Compound 1 crystallizes in the monoclinic, space group P2(1), with a = 7.1957(6) Å, b = 6.4365(5) Å, c = 13.3816(11) Å, α = 90°, β = 92.7390(10)°, γ = 90°, V = 619.06(9) Å3, Z = 2. Compound 2 crystallizes in the monoclinic, space group P2(1)/n, with a = 9.2739(8) Å, b = 4.8837(3) Å, c = 35.222(3) Å, α = 90°, β = 92.9800(10)°, γ = 90°, V = 1593.1(2) Å3, Z = 4. Compound 3 crystallizes in the orthorhombic, space group Pnma, with a = 13.1220(11) Å, b = 19.9560(16) Å, c = 6.3290(5) Å, α = 90°, β = 90°, γ = 90°, V = 1657.3(2) Å3, Z = 4. Compound 4 crystallizes in the monoclinic, space group P2(1)/c, with a = 7.0436(5) Å, b = 17.2844(13) Å, c = 13.0970(11) Å, α = 90°, β = 97.2680(10)°, γ = 90°, V = 1581.7(2) Å3, Z = 4. All supramolecular salts bear intermolecular N–H···O hydrogen bonds. Further analysis of the crystal packing of 1–4 suggests that the CH3–O and CH3–Cπ interactions also have equal importance in the structure extension as the classical hydrogen bonds. In conclusion, the discrete ions can be architectured into 1D–3D structures by the collective non-covalent interactions.

Graphical Abstract

The crystal structures of the salts from isopropylamine, cinnamic acid, 2-hydroxy-5-(phenyldiazenyl)benzoic acid, m-phthalic acid, and 2,6-pyridinedicarboxylic acid are predominantly stabilized by the classical hydrogen bonds as well as CH3–O, and CH3–Cπ interactions, leading to 1D–3D structures.

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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, Zhuji, 311800, People’s Republic of China

    Shouwen Jin, Chao Feng & Li Jin

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

    Shouwen Jin, Chao Feng, Xianhong Wen & Li Jin

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

    Daqi Wang

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  1. Shouwen Jin
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Correspondence to Shouwen Jin.

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Jin, S., Feng, C., Wen, X. et al. Crystal and Molecular Structures of Four Salts from Isopropylamine, Cinnamic Acid, 2-Hydroxy-5-(phenyldiazenyl)benzoic Acid, m-Phthalic Acid and 2,6-Pyridinedicarboxylic Acid. J Chem Crystallogr 46, 113–123 (2016). https://doi.org/10.1007/s10870-016-0634-2

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