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Investigations of this idea using titrations in low polarity solvents are impaired by interferences from ion pairing that prevent a clear picture of binding. To address this limitation and test the impact of ion\u2010ion interactions across multiple solvents, we quantified chloride binding to a cationic receptor after accounting for ion pairing. In these studies, we created a chelate receptor using aryl\u2010triazole CH donors and a quinolinium unit that directs its cationic methyl inside the binding pocket. In low\u2010polarity dichloromethane, the 1\u2009:\u20091 complex (log <jats:italic>K<\/jats:italic><jats:sub>1\u2009:\u20091<\/jats:sub> ~ 7.3) is more stable than neutral chelates, but fortuitously comparable to a preorganized macrocycle (log <jats:italic>K<\/jats:italic><jats:sub>1\u2009:\u20091<\/jats:sub> ~ 6.9). Polar acetonitrile and DMSO diminish stabilities of the charged receptor (log <jats:italic>K<\/jats:italic><jats:sub>1\u2009:\u20091<\/jats:sub> ~ 3.7 and 1.9) but surprisingly 100\u2010fold more than the macrocycle. While both receptors lose stability by dielectric screening of electrostatic stability, the cationic receptor also pays additional costs of organization. Thus even though the charged receptor has stronger binding in apolar solvents, the uncharged receptor has more anion affinity in polar solvents.<\/jats:p>","DOI":"10.1002\/chem.202302339","type":"journal-article","created":{"date-parts":[[2023,8,24]],"date-time":"2023-08-24T11:01:05Z","timestamp":1692874865000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Solvent Acts as the Referee in a Match\u2010Up Between Charged and Preorganized Receptors"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4759-135X","authenticated-orcid":false,"given":"Nabarupa","family":"Bhattacharjee","sequence":"first","affiliation":[{"name":"Department of Chemistry Indiana University Bloomington  800 E. 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