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Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy |
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| Authors: | Jona Merx Kas J. Houthuijs Dr. Hidde Elferink Eva Witlox Dr. Jasmin Mecinović Prof. Jos Oomens Dr. Jonathan Martens Dr. Thomas J. Boltje Prof. Floris P. J. T. Rutjes |
| Affiliation: | 1. Institute for Molecules and Materials, Synthetic Organic Chemistry, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands;2. Institute for Molecules and Materials, FELIX Laboratory, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands;3. Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, 5230 Odense, Denmark |
| Abstract: | N-Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N-acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N-acyliminium ions. |
| Keywords: | DFT calculations heterocycles ion spectroscopy N-acyliminium ion stereoselectivity |