化学
异核分子
席夫碱
金属
立体化学
高分子化学
组合化学
有机化学
核磁共振波谱
作者
Andrei V. Bordunov,Jerald S. Bradshaw,V. N. Pastushok,Xian X. Zhang,Xiaolan Kou,N. Kent Dalley,Zhaoxia Yang,Paul B. Savage,Reed M. Izatt
出处
期刊:Tetrahedron
[Elsevier]
日期:1997-12-01
卷期号:53 (52): 17595-17606
被引量:25
标识
DOI:10.1016/s0040-4020(97)10229-0
摘要
Abstract A simple synthetic pathway for the preparation of oxime- and Schiff base-containing aza- and diazacrown ethers is reported. N-Methoxymethyl-substituted aza-15-crown-5 and aza-18-crown-6 as well as N,N′-bis(methoxymethyl)-substituted diaza-18-crown-6 were treated with 5-bromosalicylaldehyde to produce the N-(2′-hydroxy-3′-carbonyl-5′-bromobenzyl)-substituted aza-15-crown-5 (8), aza-18-crown-6 (9) and N,N′-bis(2′-hydroxy-3′-carbonyl-5′-bromobenzyl)-substituted diaza-18-crown-6 (10) compounds. Compounds 8 and 10 were treated with hydroxylamine to give oxime-substituted ligands 12 and 13. A series of bis-Schiff base-containing diaza-18-crown-6 ligands were prepared by reacting 10 with 2-hydroxyaniline (to form 14), 5-nitro-2-hydroxyaniline (15), 2-aminopyridine (16), 2-hydrazinopyridine (17) and N-aminomorpholine (18). Compounds 12–18 are potential complexing agents for simultaneous binding of soft transition and hard alkali or alkaline earth metal ions in one molecule. These new oxime- and Schiff base-containing ligands interacted strongly with Na+ and K+ in methanol. The interaction of the aromatic portions of 9, 10, and 12–15 with transition metal ions was shown by the UV spectra of the metal ion complexes in 50% aqueous DMF. The X-ray structure of 10 is reported.
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