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Interactions in flavanone and chalcone derivatives: Hirshfeld surface analysis, energy frameworks and global reactivity descriptors
Author(s) -
Małecka Magdalena,
Chęcińska Lilianna,
Kusz Joachim,
Biernacka Marta,
Kupcewicz Bogumiła
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620001503
Subject(s) - chemistry , chalcone , flavanone , reactivity (psychology) , crystal structure , benzopyran , intermolecular force , stereochemistry , electrophile , lattice energy , computational chemistry , crystallography , medicinal chemistry , molecule , flavonoid , organic chemistry , catalysis , medicine , alternative medicine , pathology , antioxidant
The present study examines a series of flavanone and chalcone derivatives substituted with electron‐withdrawing groups (Cl or Br) and electron‐donating groups (OH, CH 3 and OCH 3 ), namely, 7‐methoxy‐2‐phenyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐one, C 16 H 14 O 3 , 2‐(4‐methoxyphenyl)‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐one, C 16 H 14 O 3 , 2‐(4‐methoxyphenyl)‐6‐methyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐one, C 17 H 16 O 3 , 2‐(4‐chlorophenyl)‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐one, C 15 H 11 ClO 2 , 8‐bromo‐6‐methyl‐2‐phenyl‐3,4‐dihydro‐2 H ‐1‐benzopyran‐4‐one, C 16 H 13 BrO 2 , (2 E )‐1‐(2‐hydroxyphenyl)‐3‐(4‐methoxyphenyl)prop‐2‐en‐1‐one, C 16 H 14 O 3 , and (2 E )‐1‐(2‐hydroxyphenyl)‐3‐(4‐hydroxyphenyl)prop‐2‐en‐1‐one, C 15 H 12 O 3 . 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.