Cocrystallization of antifungal compounds mediated by halogen bonding
- The application of halogen bonding in pharmaceutical chemistry remains a challenge. In this work, novel halogen-bonded cocrystals based on azole antifungal active pharmaceutical ingredients (APIs) and the ditopic molecule 1,4-diiodotetrafluorobenzene are reported. Their crystal structural features, spectroscopic properties, and thermal stability were studied. The components are bound through I···N from the triazole moieties present in all of the compounds. The molecular electrostatic potential (MEP) surfaces and quantum theory of atoms in molecules (QTAIM) calculations are used to rationalize the presence of hydrogen and halogen bonds in the resulting structures and their energetic analysis. The relative halogen bond ability of the different groups of voriconazole, fluconazole, and itraconazole was analyzed using MEP surfaces, demonstrating this approach to be an interesting tool to predict halogen-bonding preferences.
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| Author: | Mónica BenitoORCiDGND, Antonio Frontera, Elies Molins |
|---|---|
| URN: | urn:nbn:de:bvb:384-opus4-1044437 |
| Frontdoor URL | https://opus.bibliothek.uni-augsburg.de/opus4/104443 |
| ISSN: | 1528-7483OPAC |
| ISSN: | 1528-7505OPAC |
| Parent Title (English): | Crystal Growth & Design |
| Publisher: | American Chemical Society (ACS) |
| Type: | Article |
| Language: | English |
| Year of first Publication: | 2023 |
| Publishing Institution: | Universität Augsburg |
| Release Date: | 2023/05/19 |
| Tag: | Condensed Matter Physics; General Materials Science; General Chemistry |
| Volume: | 23 |
| Issue: | 4 |
| First Page: | 2932 |
| Last Page: | 2940 |
| DOI: | https://doi.org/10.1021/acs.cgd.3c00067 |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Licence (German): |  CC-BY 4.0: Creative Commons: Namensnennung (mit Print on Demand) |
