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.