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Synfacts 2008(4): 0367-0367  
DOI: 10.1055/s-2008-1042848
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Investigating a New Type of Hydrogen Bond

Contributor(s): Timothy M. Swager, Brett VanVeller
S. S. Zhu, H. Staats, K. Brandhorst, J. Grunenberg, F. Gruppi, E. Dalcanale, A. Lützen, K. Rissanen, C. A. Schalley*
Freie Universität Berlin, Universität Bonn and TU Braunschweig, Germany; Università di Parma, Italy and University of Jyväskylä, Finland
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

A novel complexation of neutral cavitands and anions is discussed. Resorcin­arene-based cavitands 2-11 all have acetal hydrogen atoms oriented into the cavity. Electrospray ionization Fourier-transform ion-cyclotron resonance mass spectrometry (ESI-FTICR-MS) was used to analyze the anion binding because solvent and counter ion effects could be ruled out. Collision-induced decomposition studies along with quantum chemical calculations reveal the nonaromatic C-H···anion coordination to be quite strong.