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Hydrogen Bonded 3D Supramolecular Architectures of Two Organic Salts Constructed from Saccharinate and 2-Aminoheterocyclic Compounds

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Abstract

Two saccharinate salts (6-bromobenzo[d]thiazol-2-amine):(saccharin):H2O [(HL1)+·(sac)−·H2O, L1 = 6-bromobenzo[d]thiazol-2-amine, (sac)− = saccharinate] (1), and (5,7-dimethyl-1,8-naphthyridine-2-amine):(saccharin) [(HL2)+·(sac)−, L2 = 5,7-dimethyl-1,8-naphthyridine-2-amine] (2) were prepared and structurally characterized by X-ray crystallography. Salt 1 crystallizes in the triclinic, space group P-1, with a = 7.5523(5) Å, b = 8.6498(7) Å, c = 12.7907(12) Å, α = 99.646(2), β = 90.6500(10)°, γ = 97.165(2), V = 816.87(11) Å3, Z = 2. Compound 2 crystallizes in the monoclinic, space group P2(1)/c, with a = 8.4237(12) Å, b = 8.0539(11) Å, c = 24.966(2) Å, α = 90°, β = 90.5340(10)°, γ = 90°, V = 1693.7(4) Å3, Z = 4. The different hydrogen bonding interaction modes of the saccharinate anions and the cations lead to 3D network structure, and 3D ABAB layer structure for 1, and 2, respectively. Despite variations in the aromatic organic bases, there existed strong intermolecular N–H···N, and N–H···O(carbonyl) hydrogen bonds in both compounds. At the next level, the aromatic C–H proton interacts with the sulfonyl O atom. Compound 1 bears Br–O, and π–π interactions, there are CH3–O, and CH–N interactions in 2. These interactions are responsible for the high-yielding supramolecular assembly of 2-aminoheterocyclic compounds and the saccharine into salts.

Graphical Abstract

Due to the collective weak interactions, the complexes displayed 3D structure.

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Scheme 1
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Acknowledgment

The authors are grateful for the financial support of the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the financial support of the Xinmiao project of the Education Office Foundation of Zhejiang Province (project No. 2011R412038).

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Authors and Affiliations

  1. Tianmu College ZheJiang A & F University, Lin’An, 311300, People’s Republic of China

    Shouwen Jin

  2. 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., Wang, D. Hydrogen Bonded 3D Supramolecular Architectures of Two Organic Salts Constructed from Saccharinate and 2-Aminoheterocyclic Compounds. J Chem Crystallogr 42, 767–774 (2012). https://doi.org/10.1007/s10870-012-0314-9

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  • DOI: https://doi.org/10.1007/s10870-012-0314-9

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