COMPLEXATION OF HALIDE ANIONS AND TRICARBOXYLATE ANIONS BY NEUTRAL UREA-DERIVATIZED P-TERT-BUTYLCALIX[6]ARENES

被引:178
作者
SCHEERDER, J
ENGBERSEN, JFJ
CASNATI, A
UNGARO, R
REINHOUDT, DN
机构
[1] UNIV TWENTE,ORGAN CHEM LAB,7500 AE ENSCHEDE,NETHERLANDS
[2] UNIV PARMA,INST CHIM ORGAN & IND,I-43100 PARMA,ITALY
关键词
D O I
10.1021/jo00125a035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two neutral receptors for halide anions and tricarboxylate anions have been synthesized on the basis of p-tert-butylcalix[6]arene, symmetrically functionalized with three butyl(thio)urea groups at the 1,3,5-phenolic positions. The anion complexation has been studied by H-1 NMR titration experiments, FTIR spectroscopy, and FAB mass spectrometry. The receptors bind halide and tricarboxylate anions exclusively through hydrogen bonding in a 1:1 fashion in CDCl3. For halide anions, a preference for bromide over chloride ions is observed, with a highest binding constant K-a of 1.4 x 10(3) M(-1) with receptor 4 containing the urea moieties. Thiourea receptor 5 most strongly binds 1,3,5-benzenetricarboxylate anions (K-a = 2.9 x 10(5) M(-1)) whereas 1,2,4- and 1,2,3-benzenetricarboxylate anions are complexed better by receptor 4 (K-a = 2.3 x 10(4) and 4.7 x 10(4) M(-1), respectively). An explanation for the difference in the binding of halide and tricarboxylate anions by 4 and 5 is given. The mo de of binding in the complex of 5 with 1,3,5-benzenetricarboxylate was elucidated by low-temperature NOESY spectroscopy.
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页码:6448 / 6454
页数:7
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