The fluorinated XB donor 4 is conformationally locked as synisomer, does not suffer from an unfavorable entropic contribution, and thus binds halides similarly strong as the carborane variant 3. From a topological point of view, a three-point recognition motif should be possible between the latter (3) and nitrate or phosphate, and thus they were also investigated as guests. The association to nitrate in THF and to dihydrogen phosphate in DCM (necessitated by solubility) was observed with reasonable binding strengths of approximately 3 and 4 kcal/mol, respectively (Table , entries 20/21). While this is markedly lower than the one to halides, it should be noted that halogen bond donors often perform worse for oxygen-based substrates.