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In this work, dispersion\u2010corrected density functional theory (DFT\u2010D) computations and molecular dynamics (MD) simulations were employed to understand the aggregation mechanism of AM in chloroform and water media. Our DFT\u2010D and MD analyses show that the most important interactions are those formed by the amine groups (\u2212NH<jats:sub>2<\/jats:sub>) with both the pyridine\u2010type nitrogen atoms and the carbonyl groups (C=O). In the more polar solvent, the interactions between water molecules and the C=O group prevent the AM from forming more interactions with itself. Nevertheless, four types of dimers involving N\u2212H\u2009\u22c5\u2009\u22c5\u2009\u22c5\u2009O interactions were found to exist in water solutions. The overlooked tetrel bond between endocyclic N and C atoms can also stabilize dimers in solution. Moreover, while most AM dimers are enthalpy\u2010driven, our results indicate that the unique DD\u2010AA dimer (D=donor, A=acceptor) that originates cyclic rosettes is entropy\u2010driven.<\/jats:p>","DOI":"10.1002\/cplu.202400436","type":"journal-article","created":{"date-parts":[[2024,7,25]],"date-time":"2024-07-25T09:58:42Z","timestamp":1721901522000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Probing Self\u2010Assembly of Ammeline in Chloroform and Aqueous Media: Interplay Between Hydrogen Bonding Diversity and Dimerization"],"prefix":"10.1002","volume":"89","author":[{"given":"Silvana Carina","family":"Pamies","sequence":"first","affiliation":[{"name":"Department of Chemical Engineering Centro de Investigaci\u00f3n en Qu\u00edmica e Ingenier\u00eda Te\u00f3rica y Experimental (QUITEX) Facultad Regional Resistencia Universidad Tecnol\u00f3gica Nacional  French 414 (H3500CHJ) Resistencia, Chaco Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"N\u00e9lida Mar\u00eda","family":"Peruchena","sequence":"additional","affiliation":[{"name":"Laboratorio de Estructura Molecular y Propiedades (LEMyP) Instituto de Qu\u00edmica B\u00e1sica y Aplicada del Nordeste Argentino, (IQUIBA-NEA) Consejo Nacional de Investigaciones Cient\u00edficas y T\u00e9cnicas Universidad Nacional del Nordeste (CONICET-UNNE)  Avenida Libertad 5460, 3400 Corrientes Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3807-8578","authenticated-orcid":false,"given":"Andre Nicolai","family":"Petelski","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering Centro de Investigaci\u00f3n en Qu\u00edmica e Ingenier\u00eda Te\u00f3rica y Experimental (QUITEX) Facultad Regional Resistencia Universidad Tecnol\u00f3gica Nacional  French 414 (H3500CHJ) Resistencia, Chaco Argentina"},{"name":"National Scientific and Technical Research Council (CONICET)  Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,9,13]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrneph.2011.24"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00063a030"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1080\/02773819408003114"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3RA44524K"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsanm.3c04092"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr50019a004"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2017.08.043"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.8b00231"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.5066388"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/open.201800210"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102234"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcc.9b09366"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202201010"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2018.05.046"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.200600012"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.201900042"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404927"},{"key":"e_1_2_9_18_1","unstructured":"M.\u2005J. 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