The mimicking of covalent systems using a variety of weak interactions is a constant challenge in contemporary supramolecular chemistry. Predicting and designing supramolecular architectures based on the utilization of multiple weak interactions is always a challenging task and the final assemblies are in most cases a compromise between the competing weak interactions and the geometrical constraints of the building blocks.1 Hydrogen bonds are by far the most frequently used weak interaction in the design of organic supramolecular architectures.1 Recently, the �long lost brother� the halogen bond which results from the charge transfer interaction between polarized halogen atoms and Lewis bases has been defined.2,3 Anions are general very good Lewis bases and the spherical, symmetry and electronic nature of halides makes them excellent hydrogen and halogen bond acceptors.4Resorcinarene cavitands possess pre-organized cavities suitable for guests' encapsulation.5 The cavity can be extended further through the formation of a second cavitand seam leading to the formation of deep cavity cavitands6 with enhanced binding properties. The rare combination of hydrogen and halogen bond working in tandem is explored herein, to construct container molecules analogous to cavitands6 in shape and cavity size with a huge potential for the complexation of a variety of neutral and ionic guests. A resorcinarene salt and N-methylacetamide complex.References(1) Lehn, J-M. Supramolecular Chemistry: Concepts and Perspectives, 1995 , p. 271.(2) Desiraju, G. R.; Ho, P. S.; Kloo, L.; Legon, A. C.; Marquardt, R.; Metrangolo, P.; Politzer, P.; Resnati, G. and Rissanen, K. Pure Appl. Chem., 2013  , 85, 1711.(3) Bertr�n, J. F. and Rodr�guez, M. Org. Magn. Reson., 1979  , 12, 92.(4) Beer, P. D. and Gale, P. A. Angew. Chem., Int. Ed., 2001  , 40, 486.(5) Cram, D. J. Science, 1983  , 219, 1177.(6) Srinivasan, K. and Gibb, B. C. Org. Lett., 2007  , 9, 745.

Resorcinarene salts: A new family of host compounds for neutral and ionic guests

247th National Meeting (2014)

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