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Synthesis and complexing properties of double armed diaza‐15‐crown‐5 and diaza‐18‐crown‐6 ethers having 4′‐hydroxy‐3′,5′‐disubstituted benzyl groups
Author(s) -
Habata Yoichi,
Saeki Tomomi,
Akabori Sadatoshi
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380305
Subject(s) - chemistry , potassium , crown (dentistry) , benzene , 15 crown 5 , medicinal chemistry , crown ether , mannich reaction , caesium , phenols , sodium , 18 crown 6 , organic chemistry , polymer chemistry , molecule , catalysis , ion , medicine , dentistry
A series of double armed diaza‐15‐crown‐5 ethers (9a ‐ 16a) and diaza‐18‐crown‐6 ethers (9b ‐ 16b) have been prepared by the Mannich reaction of 2,6‐disubstituted phenols with the corresponding N,N '‐dimethoxymethyldiaza‐crown ethers in benzene. The crystal structures of the diaza‐18‐crown‐6 ethers having iso ‐propyl (10b) , tert ‐butyl (11b) , and mixed methyl and tert ‐butyl groups (12b) at positions 3′ and 5′ of the phenolic side arms were determined using X‐ray diffraction methods. Competitive transport by these ligands for sodium, potassium and cesium cations were measured under basic‐source phase and acidic‐receiving phase conditions.