Structural and Electronic Characterization of Hexose Crystals: Insights into Crystal Packing and Hydrogen-Bonding Based on Crystal Density and Molecular Orbital Analysis

Tomoko Takashita (Kagawa University)
Ryunosuke Takata (Kagawa University)
Mizuki Aoe (Kagawa University)
Kei Takeshita (Fushimi Pharmaceutical Co Ltd)
Tomohiko Ishii (Kagawa University)

Advance Sustainable Science, Engineering and Technology (ASSET)
Vol. 8 No. 4 (2026): August-October

Rare sugars are monosaccharides and their derivatives that occur only in trace amounts in nature, with diverse applications anticipated in food, medicine, and agriculture. In recent years, their structural diversity has attracted increasing attention for potential applications in materials science. Although all hexoses share the same chemical formula (C₆H₁₂O₆), differences in OH group orientation can significantly alter density, crystal packing, and hydrogen bonding patterns. In this study, thirteen hexoses were analyzed to evaluate the relationship between OH group orientation and crystal density, and to quantitatively assess hydrogen bond strength using Bond Overlap Populations (BOP) calculated via the DV-Xα method. The crystal densities ranged from 1.55 to 1.68 g cm⁻³, and the BOP values typically fell within the 10⁻²-electron range, indicating moderate hydrogen bond interactions. These findings quantitatively demonstrate how subtle stereochemical variations govern crystal structures and intermolecular interactions, providing fundamental insights for designing sugar based functional materials.