Sterically congested, geminal aryl-substituted, proton-ionizable sym-dibenzo-16-crown-5 lariat ethers: synthesis and alkali metal cation extraction

被引：2
|
作者：
Tu, Chuqiao [1 ]
Jang, Youngchan [1 ]
Bates, Carrie L. [1 ]
Gega, Jerzy [1 ]
Surowiec, Kazimierz [1 ]
Bartsch, Richard A. [1 ]
机构：
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
来源：
ARKIVOC | 2010年
关键词：
Lariat ether; solvent extraction; alkali metal cations; crown ether; SOLVENT-EXTRACTION; CARBOXYLIC-ACIDS; CROWN-ETHERS;
D O I：
10.3998/ark.5550190.0011.708
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three series of proton-ionizable sym-dibenzo-16-crown-5 ethers with sterically demanding 1-naphthyl, 2-naphthyl, and 9-phenanthryl geminal groups are synthesized and characterized. Variation of the proton-ionizable group includes oxyacetic acid and N-(X) sulfonyl oxyacetamide units with X = Me, Ph, C6H4-4-NO2, and CF3. For the latter series, variation of X provides 'tunable' acidity of the ligand. The metal ion-complexing properties of the proton-ionizable sym-(aryl)dibenzo-16-crown-5 compounds are probed by competitive solvent extraction of alkali metal cations from aqueous solutions into chloroform.
引用
收藏
页码：98 / 117
页数：20
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