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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/223965
Crystallographic and Computational Analysis of Oxyma B Cocrystals with Nitrogen-Containing Coformers: The Relevant Role of <em>n</em> → π* Interactions in Their Diverse Supramolecular Architectures
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Three new cocrystals of Oxyma-B, an important racemization suppressor for peptide synthesis, with 6-methylquinoline (I), 2,3,5,6-tetramethylpyrazine (II), and 1,10-phenanthroline (III) were synthesized and their single crystal structures analyzed. They show a rich network of noncovalent interactions, including classical and nonclassical hydrogen bonds (CH···O, OH···N, CH···N), CH···π, π-stacking, and, notably, lone pair···π (n → π*) interactions. Distinctive supramolecular synthons were identified, including the R22(7) motif found in both 6-methylquinoline/Oxyma-B and 2,3,5,6-tetramethylpyrazine/Oxyma-B cocrystals. In 1,10-phenanthroline/Oxyma-B, larger ring motifs such as R44(20) and R55(24) were observed, further supported by additional synthons of types R12(5) and R12(6). Hirshfeld surface analysis and density functional theory (DFT) calculations, including MEP surface, QTAIM, and NCIplot analyses, were carried out to quantify the intermolecular contributions and rationalize the experimental findings with a focus on the cooperative role of hydrogen bonding, π-stacking, and lone pair···π (n → π*) interactions in stabilizing and shaping the architectures of these new multicomponent crystalline materials.
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JEMAI, Mahdi, et al. Crystallographic and Computational Analysis of Oxyma B Cocrystals with Nitrogen-Containing Coformers: The Relevant Role of n → π* Interactions in Their Diverse Supramolecular Architectures. Crystal Growth & Design. 2025. Vol. 25, num. 20, pags. 8503-8515. ISSN 1528-7483. [consulted: 9 of June of 2026]. Available at: https://hdl.handle.net/2445/223965