Encouraged by the promising quantum chemical results, we synthesized bidentate catalysts m/p-1 in two simple steps from commercially available bis-alkynes (Scheme 1). Therefore, the alkynes were first transformed into carborane groups, and the remaining acidic hydrogen was iodinated with strong base and elemental iodine (see SI ǂ for further details). With these compounds in hand, isothermal titration calorimetry was performed to determine the binding constants for the corresponding halide complexes in solution. The tetra-n-octylammonium salts of chloride, bromide, and iodide were chosen due to their good solubility in aprotic solvents, it had previously been shown that there is no significant impact of the choice of counter-cations on the association strength. As anticipated by the calculations, strong binding of halides was observed in THF and), albeit with significantly smaller Gibbs free energies than predicted. For p-1, the bromide adduct was indeed the most stable one, as predicted by theory. For m-1, however, the bromide and chloride complexes were similarly favorable. This again demonstrates the challenges associated with the precise modelling of halogen bonding in solution via quantum-chemical methods.