Macrocyclic bis(ureas) as ligands for anion complexation

被引:2
作者
Kretschmer, Claudia [1 ]
Dittmann, Gertrud [1 ]
Beck, Johannes [1 ]
机构
[1] Univ Bonn, Inst Inorgan Chem, D-53121 Bonn, Germany
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷
关键词
anion binding; macrocyclic compounds; NMR spectra; supramolecular chemistry; template; urea; RECOGNITION;
D O I
10.3762/bjoc.10.193
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two macrocyclic bis(ureas) 1 and 2, both based on diphenylurea, have been synthesized. Compound 1 represents the smaller ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 degrees C molecule 1 splits up into two dihydroindoloquinolinone (3) molecules. Both compounds 1 and 2 form adducts with polar molecules such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) and act as complexing agents towards a series of anions (Cl-, Br-, I-, NO3-, HSO4-). The crystal structures of 3, 2.2DMSO, 2.2DMF, and of the complex NEt4[Br.2] have been determined. Quantitative investigations of the complexation equilibria were performed via H-1 NMR titrations. While 1 is a rather weak complexing agent, the large ring of 2 binds anions with association constants up to log K = 7.93 for chloride ions.
引用
收藏
页码:1834 / 1839
页数:6
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