Anion binding involving π-acidic heteroaromatic rings

被引:487
作者
Gamez, Patrick
Mooibroek, Tiddo J.
Teat, Simon J.
Reedijk, Jan
机构
[1] Leiden Inst Chem, NL-2300 RA Leiden, Netherlands
[2] ALS, Berkeley Lab, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ar7000099
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Anions are essential species in biological systems and, particularly, in enzymesubstrate recognition. Therefore, the design and preparation of anion receptors is a topical field of supramolecular chemistry. Most hostguest systems successfully developed are based on noncovalent (ionic and hydrogen-bonded) interactions between anions and ammonium-type functionalities or Lewis acid groups. However, since the past 5 years, an alternative route toward the synthesis of efficient anion hosts has emerged, namely, the use of anionremmove interactions involving nitrogen-containing electron-deficient aromatic rings, as the result of several favorable theoretical investigations. In this Account, the state of the (new) art in this growing area of anion-binding research is presented and several selected examples from our work and that of other groups will be discussed.
引用
收藏
页码:435 / 444
页数:10
相关论文
共 56 条
[11]   Alfred Werner revisited: The coordination chemistry of anions [J].
Bowman-James, K .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (08) :671-678
[12]   N-donor ligand coordination polymers of CuII, ZnII, and CdII obtained at elevated temperature and pressure [J].
Casellas, H ;
Massera, C ;
Gamez, P ;
Lanfredi, AMM ;
Reedijk, J .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (14) :2902-2908
[13]   Crystallographic evidence of theoretically novel anion-π interactions [J].
Casellas, Helene ;
Massera, Chiara ;
Buda, Francesco ;
Gamez, Patrick ;
Reedijk, Jan .
NEW JOURNAL OF CHEMISTRY, 2006, 30 (11) :1561-1566
[14]   Arene-cation interactions of positive quadrupole moment aromatics and arene-anion interactions of negative quadrupole moment aromatics [J].
Clements, Aimee ;
Lewis, Michael .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (46) :12705-12710
[15]   An aromatic anion receptor:: Anion-π interactions do exist [J].
de Hoog, P ;
Gamez, P ;
Mutikainen, H ;
Turpeinen, U ;
Reedijk, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5815-5817
[16]   New polydentate and polynucleating N-donor ligands from amines and 2,4,6-trichloro-1,3,5-triazine [J].
de Hoog, P ;
Gamez, P ;
Driessen, WL ;
Reedijk, J .
TETRAHEDRON LETTERS, 2002, 43 (38) :6783-6786
[17]   Anion-π interactions in a carousel copper(II)-triazine complex [J].
Demeshko, S ;
Dechert, S ;
Meyer, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4508-4509
[18]   X-ray structure of a CIC chloride channel at 3.0 Å reveals the molecular basis of anion selectivity [J].
Dutzler, R ;
Campbell, EB ;
Cadene, M ;
Chait, BT ;
MacKinnon, R .
NATURE, 2002, 415 (6869) :287-294
[19]   Lone pair-aromatic interactions: To stabilize or not to stabilize [J].
Egli, Martin ;
Sarkhel, Sanjay .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (03) :197-205
[20]   Anion-π interactions in cyanuric acids:: A combined crystallographic and computational study [J].
Frontera, A ;
Saczewski, F ;
Gdaniec, M ;
Dziemidowicz-Borys, E ;
Kurland, A ;
Deyà, PM ;
Quiñonero, D ;
Garau, C .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (22) :6560-6567