Hybrids of Salicylalkylamides and Mannich Bases: Control of the Amide Conformation by Hydrogen Bonding in Solution and in the Solid State
- Dank, Christian (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna)
- Kirchknopf, Barbara (University of Applied Sciences Wiener Neustadt)
- Mastalir, Matthias (Institute of Medical Chemistry, Center of Pathobiochemistry and Genetics, Medical University of Vienna)
- Kählig, Hanspeter (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna)
- Felsinger, Susanne (Department of Organic Chemistry, Faculty of Chemistry, University of Vienna)
- Roller, Alexander (X-ray Structure Analysis Centre, Faculty of Chemistry, University of Vienna)
- Arion, Vladimir (X-ray Structure Analysis Centre, Faculty of Chemistry, University of Vienna)
- Gstach, Hubert (Institute of Medical Chemistry, Center of Pathobiochemistry and Genetics, Medical University of Vienna)
Publication date
January 2015
DOI Publisher
MDPI AG ISSN
1420-3049 Journal
1420-3049 Citation count (estimate)
2Abstract
3-Aminomethylation of salicylalkylamides afforded hybrids with a Mannich base. In addition, it triggered the rotation of the amide bond. The observed conformational switch is driven by strong intramolecular hydrogen bonding between the Mannich base and phenolic group. Crystal structure analysis reveals the stabilization of the hybrid molecules by double hydrogen bonding of the phenolic OH, which acts as an acceptor and donor simultaneously. The molecules contain an amide site and a Mannich base site in an orthogonal spatial arrangement. The intramolecular hydrogen bonds are persistent in a nonpolar solvent (e.g., chloroform). The conformational change can be reversed upon protection or protonation of the Mannich base nitrogen
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