Syntheses of Macrocyclic Di- and Tetraamides and their Binding Ability with Transition Metal Ions

  • DOHNO Reizo
    Department of Engineering Science, Faculty of Engineering, Himeji Institute of Technology
  • GOTO Shin-ichiro
    Department of Engineering Science, Faculty of Engineering, Himeji Institute of Technology
  • TANIGAWA Akira
    Department of Engineering Science, Faculty of Engineering, Himeji Institute of Technology
  • HAKUSHI Tadao
    Department of Applied Chemistry, Faculty of Engineering, Himeji Institute of Technology

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Other Title
  • 大環状ジ-およびテトラアミドの合成と遷移金属イオンの捕捉能
  • ダイカンジョウ ジ オヨビ テトラアミド ノ ゴウセイ ト センイ キンゾク

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Abstract

Four macrocyclic polyamides, 6.20-diocty1-3, 6, 9, 17, 20, 23, 29, 30-octaazatricyclo[23.3.1.111, 15]triaconta1 (29), 11, 13, 15 (30), 25, 27-hexaene-2, 10, 16, 24-tetrone (L1), 4-octy1-1, 4, 7-triazacyclotridecane8, 13-dione (L2), 4-octy1-10- (2-pyridylmethyl) -1, 4, 7, 10-tetraazacyclododecane-2, 6-dione (L3)and 4- (2-pyridylmethyl) -1, 4, 7-triazacyclotridecane-8, 13-dione (L4) have been synthesized and the composition of the complex and the extraction equilibrium constants log Kex have been determined by solvent extraction for some transition metal ions (Cu2+, Co2+, Ni2+, Zn2+ ).<BR>These ligands formed the cationic complexes as 1: 2 ( Ll: Cu2+) and 1: 1 ( L2 and L3; Cu2+), and extracted Cu2+ selectively from an equeous solution in the presence of picrate ion into 1, 2-dichloroethane. Values log Kex for the cationic complexes of Cu2+ with each ligand were increased in the order L1 < L2 < L3.<BR>In paticular, L3 possessing a pyridine ring appendage of cooperative binding extracted Cu2+ effectively even in a strong acidic equeous solution, and extracted Co2+, Ni2+, Zn2+ with same extent to Cu2+from a singl metal solution, however predominantly extracted only Cu2+ in the competitive extraction of these ions and Cu2+. L1 and L2 have little binding ability for Co2+, Ni2+ and Zn2+ ions. L4 was soluble to some extent in the equeous phase, thus it is not appropriate as a ligand of solvent extraction.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1994 (5), 435-441, 1994-05-10

    The Chemical Society of Japan

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