Calix[4]arenes containing urea and crown/urea moieties:: effects of the crown ether unit and Na+ towards anion binding ability

被引:42
作者
Tongraung, P [1 ]
Chantarasiri, N [1 ]
Tuntulani, T [1 ]
机构
[1] Chulalongkorn Univ, Fac Sci, Dept Chem, Bangkok 10330, Thailand
关键词
calix[4]arene; anion binding; ion-pair enhancement;
D O I
10.1016/S0040-4039(02)02530-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Calix[4]arenes containing urea and crown/urea moieties, 7 and 10, respectively have been synthesized. H-1 NMR titrations of 7 and 10 with anions in DMSO-d(6) showed that 7 and 10 formed complexes with Cl-, Br-, NO3- and H2PO4- to a different extent. The association constants of 7 and 10 towards anions were calculated and found to vary as H2PO4->Cl->Br-> NO3-. However, compared to 7 the presence of the crown unit in 10 resulted in a slightly higher affinity to Cl- and Br-, but a lower affinity to H2PO4-. Upon addition of Na+, the binding ability of 10 towards H2PO4- is increased due to ion-pair enhancement. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:29 / 32
页数:4
相关论文
共 15 条
[1]  
[Anonymous], 2001, Calixarenes
[2]   Neutral anion receptors: design and application [J].
Antonisse, MMG ;
Reinhoudt, DN .
CHEMICAL COMMUNICATIONS, 1998, (04) :443-448
[3]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO
[4]  
2-G
[5]   Cooperative halide, perrhenate anion-sodium cation binding and pertechnetate extraction and transport by a novel tripodal tris(amido benzo-15-crown-5) ligand [J].
Beer, PD ;
Hopkins, PK ;
McKinney, JD .
CHEMICAL COMMUNICATIONS, 1999, (13) :1253-1254
[6]   Urea derivatives of calix[4]arene 1,3-alternate:: an anion receptor with profound negative allosteric effect [J].
Budka, J ;
Lhoták, P ;
Michlová, V ;
Stibor, I .
TETRAHEDRON LETTERS, 2001, 42 (08) :1583-1586
[7]   Strong hydrogen bond-mediated complexation of H2PO4- by neutral bis-thiourea hosts [J].
Buhlmann, P ;
Nishizawa, S ;
Xiao, KP ;
Umezawa, Y .
TETRAHEDRON, 1997, 53 (05) :1647-1654
[8]   Alkali metal cation cooperative anion recognition by heteroditopic bis(calix[4]arene) rhenium(I) bipyridyl and ferrocene receptor molecules [J].
Cooper, JB ;
Drew, MGB ;
Beer, PD .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (16) :2721-2728
[9]   EQNMR - A COMPUTER-PROGRAM FOR THE CALCULATION OF STABILITY-CONSTANTS FROM NUCLEAR-MAGNETIC-RESONANCE CHEMICAL-SHIFT DATA [J].
HYNES, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (02) :311-312
[10]   Cystine-based cyclic oligoureas: a new class of hydrogen-bonding electroneutral anion receptors [J].
Ranganathan, D ;
Lakshmi, C .
CHEMICAL COMMUNICATIONS, 2001, (14) :1250-1251