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Separation and identification of enantiomers are critical for a broad range of compounds, and discriminating stereoisomers in solution remains a key analytical challenge. Nuclear Magnetic Resonance (NMR) with Matrix\u2010Assisted Diffusion\u2010Ordered Spectroscopy (MAD), in the presence of chiral resolving agents, has emerged as a tool to explore these chiral mixtures. However, insight into the intermolecular interactions that lead to chiral recognition is still limited. Here, we combine experimental MAD studies with computational approaches to investigate the enantioselective discrimination of Mandelic Acid (MA) enantiomers using (\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010BINOL and (\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010BINOL. Molecular dynamics simulations explain the differences in diffusion coefficients for heterochiral complexes. Furthermore, quantum mechanical calculations confirmed enantioselective binding preferences due to differences in Gibbs free energies, highlighting the fundamental interactions and structural criteria that explain the NMR shielding and the diffusion trends. This integrated approach bridges experimental and theoretical studies, offering a comprehensive understanding of chiral recognition mechanisms and elucidating the observed heterochiral preference of BINOL for MA enantiomers. Our findings advance the field of chiral analysis and lay a foundation for future developments for identifying stereoisomers and recognition modes underlying enantioselective binding.\n                  <\/jats:p>","DOI":"10.1002\/chem.202404694","type":"journal-article","created":{"date-parts":[[2025,3,20]],"date-time":"2025-03-20T04:14:55Z","timestamp":1742444095000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Molecular Recognition and Chiral Discrimination from NMR and Multi\u2010Scale Simulations"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3222-065X","authenticated-orcid":false,"given":"Tadeu Luiz Gomes","family":"Cabral","sequence":"first","affiliation":[{"name":"Physical Organic Chemistry Lab, Chemistry Institute University of Campinas \u2013 UNICAMP  Campinas S\u00e3o Paulo 13083\u2013970 Brazil"},{"name":"Molecular Simulations and Design Group Max Planck Institute for Dynamics of Complex Technical Systems  Magdeburg 39106 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-4303-3148","authenticated-orcid":false,"given":"Jo\u00e3o Pedro","family":"Brussolo da Silva","sequence":"additional","affiliation":[{"name":"Physical Organic Chemistry Lab, Chemistry Institute University of Campinas \u2013 UNICAMP  Campinas S\u00e3o Paulo 13083\u2013970 Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1508-0694","authenticated-orcid":false,"given":"Claudio Francisco","family":"Tormena","sequence":"additional","affiliation":[{"name":"Physical Organic Chemistry Lab, Chemistry Institute University of Campinas \u2013 UNICAMP  Campinas S\u00e3o Paulo 13083\u2013970 Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7793-0052","authenticated-orcid":false,"given":"Matthias","family":"Stein","sequence":"additional","affiliation":[{"name":"Molecular Simulations and Design Group Max Planck Institute for Dynamics of Complex Technical Systems  Magdeburg 39106 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,4,2]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.3c02239"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.4c03728"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trac.2019.115761"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.2c09010"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00661"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00846"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.3390\/ph15020240"},{"key":"e_1_2_9_9_1","unstructured":"U. 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