Pure C-H hydrogen bonding to chloride ions: A preorganized and rigid macrocyclic receptor

被引:413
作者
Li, Yongjun [1 ]
Flood, Amar H. [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
anions; coordination chemistry; hydrogen bonds; macrocyclic ligands; molecular modeling;
D O I
10.1002/anie.200704717
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Strength in numbers: When traditionally weak C-H hydrogenbonds are preorganized in a shape-persistent macrocycle, a strong affinity for chloride ions emerges. This discovery arises from the dual use of click chemistry for efficient macrocyclizationan d the favorable steric properties of the resulting 1,2,3-triazoles. (Figure Presented) © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2649 / 2652
页数:4
相关论文
共 41 条
[1]   Homochiral tripodal imidazolium receptors: structural and anion-receptor studies [J].
Alhashimy, Nameer ;
Brougham, Dermot J. ;
Howarth, Joshua ;
Farrell, Alan ;
Quilty, Brid ;
Nolan, Kieran .
TETRAHEDRON LETTERS, 2007, 48 (01) :125-128
[2]   Ring closure to β-turn mimics via copper-catalyzed azide/alkyne cycloadditions [J].
Angell, Y ;
Burgess, K .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9595-9598
[3]   Abiotic guanidinium containing receptors for anionic species [J].
Best, MD ;
Tobey, SL ;
Anslyn, EV .
COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :3-15
[4]  
Bianchi A, 1997, SUPRAMOLECULAR CHEMISTRY OF ANIONS, P217
[5]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[6]   Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide [J].
Bodine, KD ;
Gin, DY ;
Gin, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1638-1639
[7]   Alfred Werner revisited: The coordination chemistry of anions [J].
Bowman-James, K .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (08) :671-678
[8]  
Brammer L, 2001, CRYST GROWTH DES, V1, P277, DOI 10.1021/cg0l5522k
[9]   Indole-based macrocycles as a class of receptors for anions [J].
Chang, KJ ;
Moon, D ;
Lah, MS ;
Jeong, KS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7926-7929
[10]  
CHANG KJ, 2005, ANGEW CHEM, V117, P8140, DOI DOI 10.1002/ANGE.200503121