Can transacylation reactions occur via S(N)2 pathways in the gas phase? Insights via ion-molecule reactions of N-acylpyridinium ions and ab initio calculations

[reaction: see text]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 follo...

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Bibliographic Details
Published in:Organic letters 2000-08, Vol.2 (17), p.2567-2570
Main Authors: O'Hair, RA, Androutsopoulos, NK
Format: Article
Language:English
Online Access:Get full text
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Summary:[reaction: see text]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.
ISSN:1523-7052