Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding
Various functional groups have been considered as acceptors for halogen bonds, but the oxime functionality has received very little attention in this context. In this study, we focus on the analysis of the hydrogen and halogen bond preferences observed in the crystal structures of 5-halogeno-1<i&...
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| Format: | Article |
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MDPI AG
2024-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/5/1174 |
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| author | Eric Meier Wilhelm Seichter Monika Mazik |
| author_facet | Eric Meier Wilhelm Seichter Monika Mazik |
| author_sort | Eric Meier |
| collection | DOAJ |
| description | Various functional groups have been considered as acceptors for halogen bonds, but the oxime functionality has received very little attention in this context. In this study, we focus on the analysis of the hydrogen and halogen bond preferences observed in the crystal structures of 5-halogeno-1<i>H</i>-isatin-3-oximes. These molecules can be involved in various non-covalent interactions, and the competition between these interactions has a decisive influence on their self-organization. In particular, we were interested to see whether the crystal structures of 5-halogeno-1<i>H</i>-isatin-3-oximes, especially bromine- and iodine-substituted ones, are characterized by the presence of halogen bonds formed with the oxime functionality. The oxime group proved its ability to compete with the other strong donor and acceptor sites by participating in the formation of cyclic hydrogen-bonded heterosynthons oxime∙∙∙amide and O<sub>oxime</sub>∙∙∙Br/I halogen bonds. |
| first_indexed | 2024-04-25T00:23:01Z |
| format | Article |
| id | doaj.art-23df39730e264fb0bc1106e4505a789f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-25T00:23:01Z |
| publishDate | 2024-03-01 |
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| series | Molecules |
| spelling | doaj.art-23df39730e264fb0bc1106e4505a789f2024-03-12T16:51:23ZengMDPI AGMolecules1420-30492024-03-01295117410.3390/molecules29051174Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen BondingEric Meier0Wilhelm Seichter1Monika Mazik2Institut Für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Straße 29, 09596 Freiberg, GermanyInstitut Für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Straße 29, 09596 Freiberg, GermanyInstitut Für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Straße 29, 09596 Freiberg, GermanyVarious functional groups have been considered as acceptors for halogen bonds, but the oxime functionality has received very little attention in this context. In this study, we focus on the analysis of the hydrogen and halogen bond preferences observed in the crystal structures of 5-halogeno-1<i>H</i>-isatin-3-oximes. These molecules can be involved in various non-covalent interactions, and the competition between these interactions has a decisive influence on their self-organization. In particular, we were interested to see whether the crystal structures of 5-halogeno-1<i>H</i>-isatin-3-oximes, especially bromine- and iodine-substituted ones, are characterized by the presence of halogen bonds formed with the oxime functionality. The oxime group proved its ability to compete with the other strong donor and acceptor sites by participating in the formation of cyclic hydrogen-bonded heterosynthons oxime∙∙∙amide and O<sub>oxime</sub>∙∙∙Br/I halogen bonds.https://www.mdpi.com/1420-3049/29/5/1174molecular recognitionhalogen bondssupramolecular motifsoxime group |
| spellingShingle | Eric Meier Wilhelm Seichter Monika Mazik Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding Molecules molecular recognition halogen bonds supramolecular motifs oxime group |
| title | Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding |
| title_full | Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding |
| title_fullStr | Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding |
| title_full_unstemmed | Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding |
| title_short | Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1<i>H</i>-isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding |
| title_sort | combination of hydrogen and halogen bonds in the crystal structures of 5 halogeno 1 i h i isatin 3 oximes involvement of the oxime functionality in halogen bonding |
| topic | molecular recognition halogen bonds supramolecular motifs oxime group |
| url | https://www.mdpi.com/1420-3049/29/5/1174 |
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