Water and hydrogen halides serve the same structural role in a series of 2+2 hydrogen-bonded dimers based on 2,6-bis(2-anilinoethynyl)pyridine sulfonamide receptors

被引:35
作者
Berryman, Orion B. [1 ,2 ]
Johnson, Charles A., II [1 ,2 ]
Zakharov, Lev N. [1 ,2 ]
Haley, Michael M. [1 ,2 ]
Johnson, Darren W. [1 ,2 ]
机构
[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA
[2] Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA
关键词
anions; dimers; hydrogen bonds; receptors; self-assembly;
D O I
10.1002/anie.200703971
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mix and match: A new series of receptors reveals an unusual propensity to form 2+2 hydrogen-bonded dimers with water or hydrogen halides. Remarkably, water and hydrogen chloride impart nearly identical structural features to the dimers. In fact, in one case (see picture, Cl green, O red, N blue, S yellow), one water molecule and one chloride ion work in concert to form a hydrogen-bonded dimer stitched together with seven hydrogen bonds. (Figure Presented) © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:117 / 120
页数:4
相关论文
共 24 条
[1]   Hydrogen-bonded molecular capsules are stable in polar media [J].
Atwood, JL ;
Barbour, LJ ;
Jerga, A .
CHEMICAL COMMUNICATIONS, 2001, (22) :2376-2377
[2]   Structure and binding properties of water-soluble cavitands and capsules [J].
Biros, Shannon M. ;
Rebek, Julius, Jr. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (01) :93-104
[3]   Anion-directed assembly: the first fluoride-directed double helix [J].
Coles, SJ ;
Frey, JG ;
Gale, PA ;
Hursthouse, MB ;
Light, ME ;
Navakhun, K ;
Thomas, GL .
CHEMICAL COMMUNICATIONS, 2003, (05) :568-569
[4]   X-ray crystal structure and characterization of halide-binding sites of human myeloperoxidase at 1.8 Å resolution [J].
Fiedler, TJ ;
Davey, CA ;
Fenna, RE .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (16) :11964-11971
[5]   Diatomic ligand discrimination by the heme oxygenases from Neisseria meningitidis and Pseudomonas aeruginosa [J].
Friedman, Jonathan ;
Meharenna, Yergalem T. ;
Wilks, Angela ;
Poulos, Thomas L. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (02) :1066-1071
[6]   Anion-anion assembly: A new class of anionic supramolecular polymer containing 3,4-dichloro-2,5-diamido-substituted pyrrole anion dimers [J].
Gale, PA ;
Navakhun, K ;
Camiolo, S ;
Light, ME ;
Hursthouse, MB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11228-11229
[7]   Nonphosphate inhibitors of IspE protein, a kinase in the non-mevalonate pathway for isoprenoid biosynthesis and a potential target for antirnalarial therapy [J].
Hirsch, Anna K. H. ;
Lauw, Susan ;
Gersbach, Philipp ;
Schweizer, W. Bernd ;
Rohdich, Felix ;
Eisenreich, Wolfgang ;
Bacher, Adelbert ;
Diederich, Francois .
CHEMMEDCHEM, 2007, 2 (06) :806-810
[8]   Acetylcholine recognition by a deep, biomimetic pocket [J].
Hof, F ;
Trembleau, L ;
Ullrich, EC ;
Rebek, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (27) :3150-3153
[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]  
JOHNSON CA, 2007, THESIS U OREGON