Binding Modes of Nonspherical Anions to N‑Alkylammonium Resorcinarenes in the Solid State

A series of hydrogen bond stabilized N-alkylammonium resorcinarene salts with nitrate, triflate, and picrate as the counteranions were synthesized and characterized with 1H NMR and electrospray ionization (ESI) mass spectrometry. Together with electrostatic interactions, the binding of the anions with several hydrogen bond donor sites proceeds through a complex array of intra- and intermolecular hydrogen bonds, evidenced by single crystal X-ray diffraction analysis. These N-alkyl ammonium resorcinarenes bind the larger nonspherical anions into deformed cavitand-like structures and enforce a transformation of the resorcinarene conformation from almost symmetrical to extremely distorted.