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In this work, we were able to identify four structural features of barbiturates that are responsible for a certain anion affinity. The set of coordination interactions can be finely tuned with covalent decorations at the methylene group. DFT\u2010D computations at the BLYP\u2010D3(BJ)\/aug\u2010cc\u2010pVDZ level of theory show that the C\u2212H bond is as effective as the N\u2212H bond to coordinate chloride. An analysis of the electron charge density at the C\u2212H\u22c5\u22c5\u22c5Cl<jats:sup>\u2212<\/jats:sup> and N\u2212H\u22c5\u22c5\u22c5Cl<jats:sup>\u2212<\/jats:sup> bond critical points elucidates their similarities in covalent character. Our results reveal that the special acidity of the C\u2212H bond shows up when the methylene group moves out of the ring plane and it is mainly governed by the orbital interaction energy. The amide and carboxyl groups are the best choices to coordinate the ion when they act together with the C\u2212H bond. We finally show how can we use this information to rationally improve the recognition capability of a small cage\u2010like complex that is able to coordinate NaCl.<\/jats:p>","DOI":"10.1002\/cphc.202100008","type":"journal-article","created":{"date-parts":[[2021,2,5]],"date-time":"2021-02-05T21:31:19Z","timestamp":1612560679000},"page":"665-674","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Understanding the Chloride Affinity of Barbiturates for Anion Receptor Design"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3807-8578","authenticated-orcid":false,"given":"Andre Nicolai","family":"Petelski","sequence":"first","affiliation":[{"name":"Departamento de Ingenier\u00eda Qu\u00edmica Grupo de Investigaci\u00f3n en Qu\u00edmica Te\u00f3rica y Experimental (QUITEX) Universidad Tecnol\u00f3gica Nacional, Facultad Regional Resistencia  French 414 H3500CHJ) Resistencia, Chaco Argentina"},{"name":"Instituto de Qu\u00edmica B\u00e1sica y Aplicada del Nordeste Argentino IQUIBA-NEA, UNNE-CONICET  Avenida Libertad 5460 3400 Corrientes Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Josefina","family":"Marquez","sequence":"additional","affiliation":[{"name":"Departamento de Ingenier\u00eda Qu\u00edmica Grupo de Investigaci\u00f3n en Qu\u00edmica Te\u00f3rica y Experimental (QUITEX) Universidad Tecnol\u00f3gica Nacional, Facultad Regional Resistencia  French 414 H3500CHJ) Resistencia, Chaco Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Silvana Carina","family":"Pamies","sequence":"additional","affiliation":[{"name":"Departamento de Ingenier\u00eda Qu\u00edmica Grupo de Investigaci\u00f3n en Qu\u00edmica Te\u00f3rica y Experimental (QUITEX) Universidad Tecnol\u00f3gica Nacional, Facultad Regional Resistencia  French 414 H3500CHJ) Resistencia, Chaco Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gladis Laura","family":"Sosa","sequence":"additional","affiliation":[{"name":"Departamento de Ingenier\u00eda Qu\u00edmica Grupo de Investigaci\u00f3n en Qu\u00edmica Te\u00f3rica y Experimental (QUITEX) Universidad Tecnol\u00f3gica Nacional, Facultad Regional Resistencia  French 414 H3500CHJ) Resistencia, Chaco Argentina"},{"name":"Instituto de Qu\u00edmica B\u00e1sica y Aplicada del Nordeste Argentino IQUIBA-NEA, UNNE-CONICET  Avenida Libertad 5460 3400 Corrientes Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"N\u00e9lida Mar\u00eda","family":"Peruchena","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica B\u00e1sica y Aplicada del Nordeste Argentino IQUIBA-NEA, UNNE-CONICET  Avenida Libertad 5460 3400 Corrientes Argentina"},{"name":"\u00c1rea de Qu\u00edmica F\u00edsica - 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