Abstract
Heterocyclic chalcones are a recently explored subgroup of chalcones that have sparked interest due to their significant antibacterial and antifungal capabilities. Herein, we assess the structure and solubility of two such compounds, (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one and (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one. Single crystals of (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one were grown, allowing structural comparisons between the heterocyclic chalcones and (2E)-1,3-diphenylprop-2-en-1-one, trivially known as trans-chalcone. The two heterocyclic chalcones were found to be less soluble in all solvents tested and have higher melting points than trans-chalcone, likely due to their stronger intermolecular interactions arising from their heterocyclic nature. Interestingly, however, it was found that the addition of the thiophene ring in (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one increased both the melting point and solubility of the sample compared to (E)-3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one. This observation may be key for the future crystal engineering of heterocyclic chalcones for pharmaceutical applications.
Original language | English |
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Pages (from-to) | 13-17 |
Number of pages | 4 |
Journal | Acta Crystallographica Section B |
Volume | B76 |
Issue number | 1 |
DOIs | |
Publication status | Published - 1 Feb 2020 |
Keywords
- crystal structure
- heterocyclic chalcones
- solubility
- thermal stability
- intermolecular interactions
- chalcones
- crystals