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- Title
Combination of Hydrogen and Halogen Bonds in the Crystal Structures of 5-Halogeno-1 H -isatin-3-oximes: Involvement of the Oxime Functionality in Halogen Bonding.
- Authors
Meier, Eric; Seichter, Wilhelm; Mazik, Monika
- Abstract
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-1H-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-1H-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 Ooxime∙∙∙Br/I halogen bonds.
- Subjects
CRYSTAL structure; HYDROGEN bonding; BROMINE; HALOGENS; HYDROGEN analysis; FUNCTIONAL groups
- Publication
Molecules, 2024, Vol 29, Issue 5, p1174
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules29051174