Anion binding to resorcinarene-based cavitands:: The importance of C-H•••anion interactions

被引:133
作者
Zhu, Sascha S. [1 ]
Staats, Holger [2 ]
Brandhorst, Kai [6 ]
Grunenberg, Joerg [6 ]
Gruppi, Francesca [3 ,4 ]
Dalcanale, Enrico [3 ,4 ]
Luetzen, Arne [2 ]
Rissanen, Kari [5 ]
Schalley, Christoph A. [1 ,2 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
[3] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy
[4] INSTM UdR Parma, I-43100 Parma, Italy
[5] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, Jyvaskyla 40014, Finland
[6] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
关键词
anion receptors; cavitands; gas-phase chemistry; mass spectrometry; supramolecular chemistry;
D O I
10.1002/anie.200703451
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Anions rather than cations: While resorcinarenes bind cations through cation-π interactions, methylene-bridged cavitands surprisingly bind anions through C-H⋯anion interactions with the acetal protons at the wider rim (see model of the complex in the scheme). Mass spectrometry, in agreement with theory, provides evidence for anion binding on the concave side of the cavitand bowl. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:788 / 792
页数:5
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