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Complexability of o-bisguanidinobenzenes with arsenic and phosphoric acids in solution and solid states, and the potential use of their immobilized derivatives as solid base ligands for metal salts and arsenic acid

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Abstract

The role of o-bisguanidinobenzenes (BGBs) as new Brønsted base ligands for arsenic and phosphoric acids was examined. In solution state, complexation was evaluated by Job’s plot in 1H NMR experiment, indicating a 1:1 complex formation, whereas in solid state crystalline structures of complexes obtained were addressed by X-ray crystallographic analysis and/or solid state 13C NMR experiment, in which 1:2 complexes between the BGB and the acid components were normally formed. Based on these results, Merrifield and Hypogel® resin-anchored BGBs were designed and prepared as the corresponding polymer-supported host ligands. Evaluation of their coordination ability with metal salts (ZnCl2 and CoCl2) and arsenic acid in aqueous media by ICP-MS showed that the latter Hypogel® resin-anchored BGBs acted as effective immobilized base ligands.

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Abbreviations

RT:

Room temperature

THF:

Tetrahydrofuran

DMF:

Dimethylformamide

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Authors and Affiliations

  1. Department of Medicinal Organic Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba, 263-8522, Japan

    Tomoya Ito, Koji Suda, Takuya Kumamoto, Waka Nakanishi, Toshiko Watanabe & Tsutomu Ishikawa

  2. Chemical Analysis Center, Chiba University, 1-33 Yayoi, Inage, Chiba, 263-8522, Japan

    Hiroko Seki

  3. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa, 769-2193, Japan

    Masatoshi Kawahata & Kentaro Yamaguchi

  4. Department of Environmental Health, Graduate School of Pharmaceutical Sciences, Chiba University, 1-7-1, Inohana, Chuo, Chiba, 260-8522, Japan

    Yasumitsu Ogura & Kazuo T. Suzuki

Authors
  1. Tomoya Ito
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  2. Koji Suda
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  3. Takuya Kumamoto
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  4. Waka Nakanishi
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  5. Toshiko Watanabe
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  6. Tsutomu Ishikawa
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  7. Hiroko Seki
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  8. Masatoshi Kawahata
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  10. Yasumitsu Ogura
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  11. Kazuo T. Suzuki
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Correspondence to Tsutomu Ishikawa.

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Ito, T., Suda, K., Kumamoto, T. et al. Complexability of o-bisguanidinobenzenes with arsenic and phosphoric acids in solution and solid states, and the potential use of their immobilized derivatives as solid base ligands for metal salts and arsenic acid. Mol Divers 14, 131–145 (2010). https://doi.org/10.1007/s11030-009-9155-7

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  • DOI: https://doi.org/10.1007/s11030-009-9155-7

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