Interactions in flavanone and chalcone derivatives: Hirshfeld surface analysis, energy frameworks and global reactivity descriptors

Abstract

The present study examines a series of flavanone and chalcone derivatives substituted with electron‐withdrawing groups (Cl or Br) and electron‐donating groups (OH, CH3 and OCH3), namely, 7‐methoxy‐2‐phenyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C16H14O3, 2‐(4‐methoxyphenyl)‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C16H14O3, 2‐(4‐methoxyphenyl)‐6‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C17H16O3, 2‐(4‐chlorophenyl)‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C15H11ClO2, 8‐bromo‐6‐methyl‐2‐phenyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C16H13BrO2, (2E)‐1‐(2‐hydroxyphenyl)‐3‐(4‐methoxyphenyl)prop‐2‐en‐1‐one, C16H14O3, and (2E)‐1‐(2‐hydroxyphenyl)‐3‐(4‐hydroxyphenyl)prop‐2‐en‐1‐one, C15H12O3. It compares the two groups of derivatives with regard to their intermolecular interactions in the crystal lattice and lattice energy calculations, together with energy framework visualization and global reactivity descriptors (chemical hardness, chemical potential and electrophilicity index). It also discusses the relationships between different noncovalent interactions derived from Hirshfeld surface analysis, crystal lattice energy and global reactivity descriptors of the compounds.

Insights into Cocrystallization and Coamorphization Engineering Techniques in the Delivery of Traditional Chinese Medicine: Formation Mechanism, Solid-State Characterization, and Improved Pharmaceutical Properties

“…The appearance of peaks lower than 3.5 Å suggests the occurrence of hydrogen bonds. 174 64 Moreover, increasing computational modeling has been employed to simulate and predict physicochemical properties of cocrystals and coamorphous formulations, e.g., density functional theory calculations, 175 Hirshfeld surfaces analysis, 176 elastic constants calculation, 177 and energy framework calculations. 178…”

“…RDF analysis exhibited that the peaks within 1.4–1.7 Å for O 2 –H (FF)···O 6 –N 3 (OMT) and N 1 –H (FF)···O 6 –N 3 (OMT) suggested the generation of hydrogen bonding in the coamorphous system . Moreover, increasing computational modeling has been employed to simulate and predict physicochemical properties of cocrystals and coamorphous formulations, e.g., density functional theory calculations, Hirshfeld surfaces analysis, elastic constants calculation, and energy framework calculations …”