CH2+ transfer to pyridine nucleophiles: a means of producing α-distonic ions

Sophia J. Yu, Michael L. Gross, Kenneth R. Fountain

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20 Scopus citations


The distonic radical cation C5H5N+-·CH2 can be generated by the reactions of neutral pyridine with the radical cations of cyclopropane, ethylene oxide, and ketene, as well as with the [C3H6]+ ion from fragmentation of tetrahydrofuran. The distonic product ion can be distinguished from isomeric methylpyridine radical cations because the former gives characteristic [M-CH2]+, [M - CH2NCH]+, and a doubly charged ion, all of which are produced on collisional activation. Furthermore, the distonic species completely transfers CH2+ to more nucleophilic, substituted pyridines. These properties are all consistent with the assigned distonic structure. Another distonic isomer, the (3-methylene) pyridinium ion, can be distinguished from the (1-methylene)pyridinium ion on the basis of their different fragmentation behaviors. The latter ion exhibits higher stability (lower reactivity) than the prototypal [·CH2NH3+], making available a distonic species whose bimolecular reactivity can be readily investigated.

Original languageEnglish
Pages (from-to)117-124
Number of pages8
JournalJournal of the American Society for Mass Spectrometry
Issue number2
StatePublished - Feb 1993


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