2025-04-292024-07-25ChemPlusChem, Volume 89, Issue 12, e202400436 (2024)2192-6506https://hdl.handle.net/20.500.12272/12821Ammeline (AM) is a molecule with a very low reputation in the field of supramolecular community, but with a recently proven potential both experimentally and theoretically. In this work, dispersion-corrected density functional theory (DFT-D) computations and molecular dynamics (MD) simulations were employed to understand the aggregation mechanism of AM in chloroform and water media. Our DFT-D and MD analyses show that the most important interactions are those formed by the amine groups (−NH2) with both the pyridine-type 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−H∙∙∙O 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-driven, our results indicate that the unique DD-AA dimer (D=donor, A=acceptor) that originates cyclic rosettes is entropy- driven.pdfenAttribution-NonCommercial-ShareAlike 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-sa/4.0/dimerizationhydrogen bondsmolecular dynamicsnoncovalent interactionssupramolecular chemistryinfo:eu-repo/semantics/articleAcceso abiertohttps://doi.org/10.1002/cplu.2024004362025-07-25