Collisionally activated dissociation of N-acylpyridinium cations
- 1 January 1998
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 835-840
- https://doi.org/10.1039/a706086f
Abstract
Relative fragmentation energies of a variety of N-acylpyridinium cations have been measured in the gas phase by electrospray ionization (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FTICRMS). N-Aroyl- and N-heteroaroyl-pyridinium cations dissociated to give free ArCO+ ions with activation energies which are strongly decreased/increased by stabilizing/destabilizing electron-donor/acceptor substituents in the aroyl group. N-Alkylcarbonyl- and N-phenoxycarbonyl-pyridinium cations fragment via ion molecule complexes which dissociate to pyridinium cation and ketene or CO2 + aryne. N-Alkoxycarbonylpyridinium cations form pyridinium cations via detectable N-carboxypyridinium cations. The propensity of those cations to undergo SN1 or SN2 reactions is discussed.Keywords
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