Synlett 2013; 24(19): 2510-2514
DOI: 10.1055/s-0033-1338980
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© Georg Thieme Verlag Stuttgart · New York

Immobilized 1,2-Bis(guanidinoalkyl)benzenes: Potentially Useful for the Purification of Arsenic-Polluted Water

Noriyuki Suzuki*
a  Department of Medicinal Organic Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba 260-8675, Japan   Fax: +81(43)2262919   Email: n-suzuki@chiba-u.jp   Fax: +81(43)2262944   Email: benti@faculty.chiba-u.jp
,
Kaito Kishimoto
a  Department of Medicinal Organic Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba 260-8675, Japan   Fax: +81(43)2262919   Email: n-suzuki@chiba-u.jp   Fax: +81(43)2262944   Email: benti@faculty.chiba-u.jp
,
Kohei Yamazaki
a  Department of Medicinal Organic Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba 260-8675, Japan   Fax: +81(43)2262919   Email: n-suzuki@chiba-u.jp   Fax: +81(43)2262944   Email: benti@faculty.chiba-u.jp
,
Takuya Kumamoto
a  Department of Medicinal Organic Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba 260-8675, Japan   Fax: +81(43)2262919   Email: n-suzuki@chiba-u.jp   Fax: +81(43)2262944   Email: benti@faculty.chiba-u.jp
,
Tsutomu Ishikawa*
a  Department of Medicinal Organic Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo, Chiba 260-8675, Japan   Fax: +81(43)2262919   Email: n-suzuki@chiba-u.jp   Fax: +81(43)2262944   Email: benti@faculty.chiba-u.jp
,
Davor Margetić
b  Laboratory for Physical-Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruder Bošković Institute, Bijenicka c. 54, 10001 Zagreb, Croatia
› Author Affiliations
Further Information

Publication History

Received: 11 September 2013

Accepted: 17 September 2013

Publication Date:
14 October 2013 (online)


Abstract

Guanidines can act as ligands for various organic and inorganic ions. We have previously synthesized polymer-supported aromatic bisguanidine derivatives and evaluated their potential for removing arsenic from polluted water. In this work, we designed and synthesized the corresponding aliphatic bisguanidine derivatives, and we demonstrated that they show greater affinity for arsenic acid than do the previous aromatic ligands. The newly synthesized HypoGel resin-anchored aliphatic bisguanidines might serve as useful recyclable scavengers for the removal of arsenic from polluted water.

Supporting Information

 
  • References and Notes

  • 1 Bissen M, Frimmel FH. Acta Hydrochim. Hydrobiol. 2003; 31: 9
  • 2 Bissen M, Frimmel FH. Acta Hydrochim. Hydrobiol. 2003; 31: 97
  • 3 Meharg A. Venomous Earth: How Arsenic Caused the World’s Worst Mass Poisoning. Macmillan; Basingstoke: 2005
  • 4 Short PL. Chem. Eng. News 2007; 85 (17) 13
  • 5 Ishikawa T, Kumamoto T. Synthesis 2006; 737
  • 6 Ishikawa T. Superbases for Organic Synthesis: Guanidines, Amidines and Phosphazenes and Related Organocatalysts. Wiley; Chichester: 2009
    • 7a For anions, see: Wiskur SL, Lavigne JJ, Metzger A, Tobey SL, Lynch V, Anslyn EV. Chem. Eur. J. 2004; 10: 3792
    • 7b For metals, see: Bienemann O, Hoffmann A, Herres-Pawlis S. Rev. Inorg. Chem. 2011; 31: 83
  • 8 Ishikawa T. Chem. Pharm. Bull. 2010; 58: 1555 ; and references cited therein
  • 9 Kawahata M, Yamaguchi K, Ishikawa T. Cryst. Growth Des. 2005; 5: 373
  • 10 Kawahata M, Shikii K, Seki H, Ishikawa T, Yamaguchi K. Chem. Pharm. Bull. 2006; 54: 147
  • 11 Kawahata M, Yamaguchi K, Ito T, Ishikawa T. Acta Crystallogr., Sect. E 2006; 62: o3301
  • 12 Suda K, Saito N, Kumamoto T, Nakanishi W, Kawahata M, Yamaguchi K, Ogra Y, Suzuki KT, Ishikawa T. Heterocycles 2009; 77: 375
  • 13 Ito T, Suda K, Kumamoto T, Nakanishi W, Watanabe T, Ishikawa T, Seki H, Kawahata M, Yamaguchi K, Ogra Y, Suzuki KT. Mol. Diversity 2010; 14: 131
  • 14 Handbook of Chemistry and Physics . Weast RC. CRC Press; Cleveland, Ohio: 1974. 55th ed., D-130
  • 15 Obtained by the B3LYP/6-31G*+E vib(B3LYP/6-31G*) method, see: Margetić D, Trošelj P, Ishikawa T, Kumamoto T. Bull. Chem. Soc. Jpn. 2010; 83: 1055
  • 16 Kawahara S, Uchimaru T. Z. Naturforsch., B 2000; 55: 985
  • 17 Isobe T, Ishikawa T. J. Org. Chem. 2001; 99: 7770
  • 18 Pettit GR, Quistorf PD, Fry JA, Herald LD, Hamel E, Chapuois JC. J. J. Nat. Prod. 2009; 72: 876
  • 19 Caddick S, Judd DB, Lewis AK. K, Reicha MT, Williams MR. V. Tetrahedron 2003; 59: 5417
  • 20 Zoń J, Miziak P, Amrhein N, Gancarz R. Chemistry & Biodiversity 2005; 2: 1187