{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T10:57:32Z","timestamp":1769857052770,"version":"3.49.0"},"reference-count":38,"publisher":"Wiley","issue":"41","license":[{"start":{"date-parts":[[2018,10,1]],"date-time":"2018-10-01T00:00:00Z","timestamp":1538352000000},"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":[[2018,11,8]]},"abstract":"<jats:p>Tetraureido\u2010dihomooxacalix[4]arenes (<jats:italic>tert<\/jats:italic>\u2010butyl <jats:bold>4a<\/jats:bold> and phenyl <jats:bold>4b<\/jats:bold>) were synthesised and obtained in a partial cone conformation in solution and in the solid state, as confirmed by NMR and X\u2010ray diffraction studies. Their complexation ability towards halides, pseudo\u2010halides and oxoanions was assessed by <jats:sup>1<\/jats:sup>H NMR and UV\/Vis titrations. Structural and energetic insights of phenylurea <jats:bold>4b<\/jats:bold> complexes were also obtained using molecular dynamics (MD) simulations. The binding data showed that the association constants are strongly dependent on the nature of the substituent (alkyl\/aryl) at the urea unit. <jats:italic>tert<\/jats:italic>\u2010Butyl urea <jats:bold>4a<\/jats:bold> is a much weaker receptor than phenylurea <jats:bold>4b<\/jats:bold>, and showed association constants that decrease with decreasing of anion basicity. Phenylurea <jats:bold>4b<\/jats:bold> is a highly efficient anion receptor, exhibiting a remarkable binding ability towards BzO<jats:sup>\u2013<\/jats:sup> ion (log\u2009<jats:italic>K<\/jats:italic><jats:sub>ass<\/jats:sub> = 4.81). In comparison to the phenylurea analogue bearing a butyl spacer and a cone conformation, receptor <jats:bold>4b<\/jats:bold> containing a shorter spacer (three carbon atoms) and a partial cone conformation is more pre\u2010organized, displaying a strong enhancement of its binding efficiency. MD simulations have shown that the anions are preferentially bound to the urea moieties of the macrocycle lower rim, in agreement with the ROESY spectrum carried out with phenylurea <jats:bold>4b<\/jats:bold> and BzO<jats:sup>\u2013<\/jats:sup> anion.<\/jats:p>","DOI":"10.1002\/ejoc.201800880","type":"journal-article","created":{"date-parts":[[2018,9,16]],"date-time":"2018-09-16T22:00:33Z","timestamp":1537135233000},"page":"5657-5667","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Anion Recognition by Partial Cone Dihomooxacalix[4]arene\u2010Based Receptors Bearing Urea Groups: Remarkable Affinity for Benzoate Ion"],"prefix":"10.1002","volume":"2018","author":[{"given":"Ana S.","family":"Augusto","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":"Alexandre S.","family":"Miranda","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Faculdade de Ci\u00eancias da Universidade de Lisboa  Edif\u00edcio C8 1749\u2010016 Lisboa Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5535-2500","authenticated-orcid":false,"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":"Margarida Q.","family":"Miranda","sequence":"additional","affiliation":[{"name":"Department of Chemistry CICECO \u2010 Aveiro Institute of Materials University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9380-0418","authenticated-orcid":false,"given":"V\u00edtor","family":"F\u00e9lix","sequence":"additional","affiliation":[{"name":"Department of Chemistry CICECO \u2010 Aveiro Institute of Materials University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"Giovanna","family":"Brancatelli","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":"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"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0711-5113","authenticated-orcid":false,"given":"Silvano","family":"Geremia","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"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7297-5139","authenticated-orcid":false,"given":"Paula M.","family":"Marcos","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Faculdade de Ci\u00eancias da Universidade de Lisboa  Edif\u00edcio C8 1749\u2010016 Lisboa Portugal"},{"name":"Faculdade de Farm\u00e1cia da Universidade de Lisboa  Av. 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