Solution Phase Measurement of Both Weak σ and C−H···X⁻ Hydrogen Bonding Interactions in Synthetic Anion Receptors

A series of tripodal receptors preorganize electron-deficient aromatic rings to bind halides in organic solvents using weak sigma anion-to-arene interactions or C-H...X- hydrogen bonds. 1H NMR spectroscopy proves to be a powerful technique for quantifying binding in solution and determining the interaction motifs, even in cases of weak binding.