Study of Radical Merostabilization by Electrospray FTICR/MS

The threshold fragmentation energies (E o ) of three different 4-(1‘-substituted-2‘-phenethyl)-1-methylpyridinium salts containing a neutral, an electron-donor, or an electron-acceptor group as α-substituent, respectively, were measured by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1996-11, Vol.118 (47), p.11905-11911
Main Authors: Katritzky, Alan R, Shipkova, Petia A, Qi, Ming, Nichols, Daniel A, Burton, Richard D, Watson, Clifford H, Eyler, John R, Tamm, Toomas, Karelson, Mati, Zerner, Michael C
Format: Article
Language:English
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Summary:The threshold fragmentation energies (E o ) of three different 4-(1‘-substituted-2‘-phenethyl)-1-methylpyridinium salts containing a neutral, an electron-donor, or an electron-acceptor group as α-substituent, respectively, were measured by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FTICR/MS) collisionally activated dissociation (CAD). N-Methyl-4-(1-ethoxy-2-phenylethyl)pyridinium iodide (10), containing both electron-donor and electron-acceptor substituent groups, has a significantly lower E o than the analogs containing a benzyl (6) or benzoyl (7) substituent. This was ascribed to merostabilization of the corresponding radical 19, and this conclusion was further supported by theoretical calculations.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja962027h