{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,8]],"date-time":"2025-12-08T22:27:43Z","timestamp":1765232863704,"version":"build-2065373602"},"reference-count":47,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2020,3,20]],"date-time":"2020-03-20T00:00:00Z","timestamp":1584662400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2020,4,7]]},"abstract":"<jats:p>Hexahomotrioxacalix[3]arene\u2010based receptors (phenylurea <jats:bold>4a<\/jats:bold>, phenylthiourea <jats:bold>4b<\/jats:bold> and <jats:italic>tert<\/jats:italic>\u2010butylurea <jats:bold>4c<\/jats:bold>) were synthesised and obtained in the partial cone conformation in solution. Phenylurea <jats:bold>4a<\/jats:bold> was also obtained in the cone conformation and its X\u2010ray crystal structure is reported. Their binding properties towards several anions of different geometries were studied by <jats:sup>1<\/jats:sup>H NMR titrations. The data showed that phenylurea cone <jats:bold>4a<\/jats:bold> is the best anion receptor, displaying a very high affinity for the carboxylates AcO<jats:sup>\u2013<\/jats:sup> and BzO<jats:sup>\u2013<\/jats:sup> anions (log\u2009<jats:italic>K<\/jats:italic><jats:sub>ass<\/jats:sub> = 4.12 and 4.00, respectively). Phenylurea partial cone <jats:bold>4a<\/jats:bold> and phenylthiourea <jats:bold>4b<\/jats:bold>, although weaker, are still reasonably good receptors, showing the same trend as cone <jats:bold>4a<\/jats:bold>. <jats:italic>tert<\/jats:italic>\u2010Butylurea <jats:bold>4c<\/jats:bold> exhibited very low affinity for all the anions, confirming that the association constants strongly depend on the nature of the substituent (aryl\/alkyl) at the urea moiety. In addition, cone and partial cone <jats:bold>4a<\/jats:bold> derivatives were also tested in the recognition of <jats:italic>n<\/jats:italic>\u2010alkylammonium salts and cone <jats:bold>4a<\/jats:bold> also as a ditopic receptor for biogenic amine hydrochlorides by <jats:sup>1<\/jats:sup>H NMR titrations. Cone <jats:bold>4a<\/jats:bold> showed an outstanding affinity for the guest alkylammonium and amines, even at 298 K and in a more competitive solvent such as CDCl<jats:sub>3<\/jats:sub>\/[D<jats:sub>6<\/jats:sub>]DMSO mixture. DFT calculations corroborated the NMR observations.<\/jats:p>","DOI":"10.1002\/ejoc.201901888","type":"journal-article","created":{"date-parts":[[2020,2,27]],"date-time":"2020-02-27T12:55:16Z","timestamp":1582808116000},"page":"1930-1940","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Recognition of Anions, Monoamine Neurotransmitter and Trace Amine Hydrochlorides by Ureido\u2010Hexahomotrioxacalix[3]arene Ditopic Receptors"],"prefix":"10.1002","volume":"2020","author":[{"given":"Filipa A.","family":"Teixeira","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Faculdade de Ci\u00eancias da Universidade de Lisboa  Edif\u00edcio C8 1749\u2010016 Lisboa Portugal"}]},{"given":"Jos\u00e9 R.","family":"Ascenso","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Instituto Superior T\u00e9cnico  Complexo I, Av. Rovisco Pais 1049\u2010001 Lisboa Portugal"}]},{"given":"Peter J.","family":"Cragg","sequence":"additional","affiliation":[{"name":"School of Pharmacy and Biomolecular Sciences Huxley Building University of Brighton  BN2 4GJ Brighton UK"}]},{"given":"Neal","family":"Hickey","sequence":"additional","affiliation":[{"name":"Centre of Excellence in Biocrystallography Department of Chemical and Pharmaceutical Sciences University of Trieste  via L. Giorgieri 1 34127 Trieste Italy"}]},{"given":"Silvano","family":"Geremia","sequence":"additional","affiliation":[{"name":"Centre of Excellence in Biocrystallography Department of Chemical and Pharmaceutical Sciences University of Trieste  via L. 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