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Our results elucidate a synergistic interplay between hydrogen bonding and \u03c0\u2013\u03c0 stacking, where London dispersion accounts for over 50% of the total attractive forces. The wide HOMO\u2013LUMO gaps (7.2\u20139.4 eV) obtained with M06\u20132X and \u03c9B97X correlate with minimal induction contributions (Eind &amp;lt; 9.5%) and negligible charge transfer, confirming the noncovalent nature of the assembly. A detailed thermochemical analysis confirms the spontaneity of dimerization through calculated Gibbs free energies, revealing a strong dependence on the chosen density functional. Furthermore, color-coded NCI-RDG plots provide an unambiguous mapping of attractive and steric forces, demonstrating that while dimerization preserves monomeric reactivity, it drives a stable supramolecular assembly. These insights provide a fundamental starting point for understanding the intrinsic driving forces of methylxanthines, potentially aiding in the future rational design of methylxanthine-based cocrystals and supramolecular materials.<\/jats:p>","DOI":"10.1021\/acsomega.6c02053","type":"journal-article","created":{"date-parts":[[2026,8,10]],"date-time":"2026-08-10T18:02:12Z","timestamp":1786384932000},"page":"49268-49279","source":"Crossref","is-referenced-by-count":0,"title":["Theoretical Analysis\nof Electronic, Vibrational Properties,\nand Noncovalent Interactions in Methylxanthines: Monomers to Antiparallel\nDimers"],"prefix":"10.1021","volume":"11","author":[{"given":"Rau\u0301l","family":"Mendoza-Ba\u0301ez","sequence":"first","affiliation":[{"name":"Centro de Investigacio\u0301n y de Estudios Avanzados del IPN (Cinvestav) , , Avenida IPN 2508, Col. 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