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The double H\u2010bond donor pattern is achieved by the introduction of a sulfonamide group in the C\u20108 position of naphthalene and a carboxamide at the C\u20102 position. This cleft, for which the geometry resembles that of an oxyanion hole, is able to adjust to different guests, as shown by the analysis of the X\u2010ray crystal structures of associates with methanol or acetic acid. Combination of hydrogen bonds and charge\u2010transfer interactions led to further stabilization of the complexes, in which the electron\u2010rich aromatic ring of the receptor was close in space to the electron\u2010deficient dinitroaromatic guests. Modelling studies and bidimensional NMR experiments have been carried out to provide additional information.<\/jats:p>","DOI":"10.1002\/chem.202102137","type":"journal-article","created":{"date-parts":[[2021,8,15]],"date-time":"2021-08-15T22:50:20Z","timestamp":1629067820000},"page":"14605-14609","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["An Adjustable Cleft Based on an 8\u2010Sulfonamide\u20102\u2010Naphthoic Acid with Oxyanion Hole Geometry"],"prefix":"10.1002","volume":"27","author":[{"given":"Jos\u00e9 J.","family":"Garrido\u2010Gonz\u00e1lez","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad de Salamanca  Plaza de los Ca\u00eddos s\/n Salamanca 37008 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Irene","family":"Boya del Teso","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad de Salamanca  Plaza de los Ca\u00eddos s\/n Salamanca 37008 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u00c1ngel L.","family":"Fuentes de Arriba","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad de Salamanca  Plaza de los Ca\u00eddos s\/n Salamanca 37008 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Francisca","family":"Sanz","sequence":"additional","affiliation":[{"name":"Servicio de Difracci\u00f3n de Rayos X University of Salamanca  Plaza de los Ca\u00eddos s\/n Salamanca 37008 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eva M.","family":"Mart\u00edn del Valle","sequence":"additional","affiliation":[{"name":"Departamento de Ingenier\u00eda Qu\u00edmica Universidad de Salamanca  Plaza de los Ca\u00eddos s\/n Salamanca 37008 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joaqu\u00edn R.","family":"Mor\u00e1n","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad de Salamanca  Plaza de los Ca\u00eddos s\/n Salamanca 37008 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Victoria","family":"Alc\u00e1zar","sequence":"additional","affiliation":[{"name":"Departamento de Ingenier\u00eda Qu\u00edmica Industrial y del Medio Ambiente Universidad Polit\u00e9cnica de Madrid  C\/Jos\u00e9 Guti\u00e9rrez Abascal, 2 Madrid 28006 Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,9,27]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00435a001"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.83.11.3743"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50100a004"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(68)80043-9"},{"key":"e_1_2_2_6_1","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.273.40.25529"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.8b00217"},{"key":"e_1_2_2_9_1","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00212a065"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00176a048"},{"key":"e_1_2_2_12_1","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199207921"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19921040627"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/CC9960002529"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39940001277"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202012315"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202012315"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB01435F"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules191220751"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201200251"},{"key":"e_1_2_2_21_2","first-page":"1325","volume-title":"Supramolecular Chemistry: From Molecules to Nanomaterials","author":"Wilson A. 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