Anion-π interactions are genuine noncovalent interactions despite the initial ambiguity surrounding their existence. This ambiguity originated because having anions interact with π-rings seems electrostatically counterintuitive. However, numerous theoretical studies have established that placing an anion in proximity to a polarizable/electron-deficient π-ring lead to different anion-π motifs, including forming an anion-π bond. Yet, there is no experimental evidence of energetic anion-π interaction in the solution that parallels gas-phase estimations. For instance, the interactions between fluorine and π-acidic rings range between 7.8 - 28 kcal/mol in the gas phase based on MP2/6-31++G** level calculations. Yet equivalent measurements in organic solvents are typically less than 1 kcal/mol. In this study, we report an energetic anion-π interaction in DMSO using a synthetic model system

Evidence of strong anion-π interactions in DMSO

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