LITHIUM ION-SELECTIVE ALKYLPHOSPHORIC ACID ARMED DIBENZO-14-CROWN-4 AND BENZO-14-CROWN-4 DERIVATIVES

被引:23
作者
HABATA, Y
IKEDA, M
AKABORI, S
机构
[1] Department of Chemistry, Faculty of Science, Toho University, Funabashi
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 20期
关键词
D O I
10.1039/p19920002651
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New dibenzo- 2 and benzo-14-crown-4 derivatives 4a-c having an ionizable alkyl phosphoric acid moiety as an additional pendant arm binding site have been synthesized. Their complexing abilities have been measured by solvent extraction and transport experiments. It is shown that introduction of the pendant group into the dibenzo- and benzo-14-crown-4 derivatives significantly enhances their ability to extract and transport Li+ ion. IR spectroscopy, fast atom bombardment (FAB) mass spectrometry and C-13 NMR spectroscopy were used to study the structure of the complex of 2 with Li+ ion. From these results, it was suggested that Li + ion is strongly bound by both the crown oxygen and the phosphate anion of the side arm and is predominantly coordinated by the phosphate anion and the nearest oxygen atoms to the pendant site of the crown ring.
引用
收藏
页码:2651 / 2655
页数:5
相关论文
共 22 条
[1]   HIGH LITHIUM SELECTIVITY IN COMPETITIVE ALKALI-METAL SOLVENT-EXTRACTION BY LIPOPHILIC CROWN CARBOXYLIC-ACIDS [J].
BARTSCH, RA ;
CZECH, BP ;
KANG, SI ;
STEWART, LE ;
WALKOWIAK, W ;
CHAREWICZ, WA ;
HEO, GS ;
SON, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (17) :4997-4998
[2]   SYNTHESIS OF HIGHLY LIPOPHILIC CROWN ETHER CARBOXYLIC-ACIDS [J].
BARTSCH, RA ;
LIU, Y ;
KANG, SI ;
SON, B ;
HEO, GS ;
HIPES, PG ;
BILLS, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4864-4869
[3]  
CLERC P, 1981, STRUKTURAUFKLARUNG O, P1235
[4]   FUNCTIONALIZED 13-CROWN-4, 14-CROWN-4, 15-CROWN-4, AND 16-CROWN-4 COMPOUNDS - SYNTHESIS AND LITHIUM ION COMPLEXATION [J].
CZECH, BP ;
BABB, DA ;
SON, B ;
BARTSCH, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4805-4810
[5]  
CZECH BP, 1986, J HETEROCYCLIC CHEM, V23, P465
[6]   LITHIUM ION-SELECTIVE DIBENZO-14-CROWN-4 POSSESSING A PHOSPHORIC-ACID FUNCTIONAL-GROUP AS A PENDANT [J].
HABATA, Y ;
IKEDA, M ;
AKABORI, S .
TETRAHEDRON LETTERS, 1992, 33 (22) :3157-3160
[7]  
HABATA Y, IN PRESS TETRAHEDRON
[8]   INTRAMOLECULAR [2+2] PHOTOCYCLOADDITION .11. LI+ ION-SELECTIVE TRANSPORT BY CROWNOPHANES [J].
INOKUMA, S ;
KATOH, R ;
YAMAMOTO, T ;
NISHIMURA, J .
CHEMISTRY LETTERS, 1991, (10) :1751-1754
[9]   PROTON IONIZABLE CROWN COMPOUNDS .18. COMPARISON OF ALKALI-METAL TRANSPORT IN A H2O-CH2CL2-H2O LIQUID MEMBRANE SYSTEM BY 4 PROTON-IONIZABLE MACROCYCLES CONTAINING THE DIALKYLHYDROGENPHOSPHATE MOIETY [J].
IZATT, RM ;
LINDH, GC ;
HUSZTHY, P ;
CLARK, GA ;
BRUENING, RL ;
BRADSHAW, JS ;
CHRISTENSEN, JJ .
JOURNAL OF INCLUSION PHENOMENA, 1989, 7 (05) :501-509
[10]   MACROCYCLIC LIGANDS EXAMINED BY FAST ATOM BOMBARDMENT MASS-SPECTROMETRY - DIRECT OBSERVATION OF METAL CATION SELECTIVITY IN COMPLEXATION [J].
JOHNSTONE, RAW ;
ROSE, ME .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (21) :1268-1270