Can Transacylation Reactions Occur via SN2 Pathways in the Gas Phase? Insights via Ion−Molecule Reactions of N-Acylpyridinium Ions and ab Initio Calculations
- 1 August 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (17) , 2567-2570
- https://doi.org/10.1021/ol006060r
Abstract
The gas-phase identity exchange reactions of N-acylpyridinium ions with pyridine have been examined experimentally in an ion trap mass spectrometer through the use of isotope labeling experiments. The nature of the acyl group plays a crucial role, with the bimolecular rates following the order acetyl > benzoyl > N,N-dimethylaminocarbamyl. The experimental results correlate with ab initio calculations on the simple model system RC(O)NH3+ + NH3, which also demonstrates that these are “SN2 like” processes.This publication has 14 references indexed in Scilit:
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