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DOI: 10.1039/A706086F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 835-840

Collisionally activated dissociation of N-acylpyridinium cations

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Alan R. Katritzky, Richard D. Burton, Petia A. Shipkova, Ming Qi, Clifford H. Watson and John R. Eyler

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.

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