Geometrically diverse anions in anion–π interactions

Michael Giese Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany

Markus Albrecht Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, GermanyCorrespondence[email protected]

Gergana Ivanova Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany

Arto Valkonen Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, FIN-40014, Jyväskylä, Finland

Kari Rissanen Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, FIN-40014, Jyväskylä, Finland

Abstract

The role of different anion geometries in anion–π interactions is discussed. The chemistry described herein is different to the interaction of spherical cations with aromatics. The influence of different geometries makes selective anion recognition more complicated than respective cation sensing. The present structural study reveals attractive interactions between pentafluorophenyl units and geometrically diverse anions (linear, trigonal planar, tetrahedral and octahedral). Due to the electrostatic nature of anion–π interactions, the anion geometry seems to be irrelevant. The size of the anion controls the relative orientation of the anion and the π system (e.g. in compounds 1–3). The dimeric solid-state structure of ammonium tetrafluorophenolate betaine 4 shows π–π as well as anion–π interactions. In the solid-state structure of 5, the linear BrIBr anion is panelled by three pentafluorophenyl units.

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