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The structures and forces involved in ethanol aggregation have been investigated using microwave spectroscopy and extensive quantum chemical calculations. Four isomers of the ethanol trimer have been observed and identified based on comparisons between experimental and predicted spectroscopic parameters, and considering collisional relaxation in the supersonic expansion. All observed isomers exhibit O\u2212H\nO hydrogen bonds between the hydroxyl groups forming a six\u2010membered ring. Additionally, secondary C\u2212H\nO hydrogen bonds and H\nH dispersion contacts participate in the stabilization of the complexes with remarkably similar energy contributions. Structures where there is a mixture of\n                    <jats:italic>gauche<\/jats:italic>\n                    and\n                    <jats:italic>trans<\/jats:italic>\n                    conformations of ethanol are favored, with\n                    <jats:italic>gauche<\/jats:italic>\n                    conformations being predominant and no evidence of homochirality synchronization. Our results underscore the critical changes involved in aggregation as the size of the system increases and shed light on the unique properties and behavior of ethanol in chemical and biological systems.\n                  <\/jats:p>","DOI":"10.1002\/anie.202415229","type":"journal-article","created":{"date-parts":[[2024,11,29]],"date-time":"2024-11-29T14:29:04Z","timestamp":1732890544000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Alcohol Self\u2010Aggregation: the Preferred Configurations of the Ethanol Trimer"],"prefix":"10.1002","volume":"64","author":[{"given":"S.","family":"Indira Murugachandran","sequence":"first","affiliation":[{"name":"Department of Chemistry King's College London  London SE1 1DB United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isabel","family":"Pe\u00f1a","sequence":"additional","affiliation":[{"name":"Department of Chemistry King's College London  London SE1 1DB United Kingdom"},{"name":"Present address: Departamento de Qu\u00edmica F\u00edsica y Qu\u00edmica Inorg\u00e1nica Facultad de Ciencias-I.U. CINQUIMA Universidad de Valladolid  Paseo de Bel\u00e9n 7 Valladolid 47011 Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Al","family":"Mokhtar Lamsabhi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica &amp; Institute for Advanced Research in Chemical Sciences (IAdChem) Universidad Aut\u00f3noma de Madrid  Cantoblanco 28049 Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manuel","family":"Y\u00e1\u00f1ez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica &amp; Institute for Advanced Research in Chemical Sciences (IAdChem) Universidad Aut\u00f3noma de Madrid  Cantoblanco 28049 Madrid Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7531-0140","authenticated-orcid":false,"given":"M.","family":"Eugenia Sanz","sequence":"additional","affiliation":[{"name":"Department of Chemistry King's College London  London SE1 1DB United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,12,9]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010518)40:10<1808::AID-ANIE1808>3.0.CO;2-1"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1080\/00268979909482847"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.191266498"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00512"},{"key":"e_1_2_8_5_1","first-page":"1","volume":"142","author":"Suhm M. 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