Abstract
The distonic radical cation C 5H 5 N + ĊH 2 can be generated by the reactions of neutral pyridine with the radical cations of cyclopropane, ethylene oxide, and ketene, as well as with the [C 3H 6] +· ion from fragmentation of tetrahydrofuran. The distonic product ion can be distinguished from isomeric methylpyridine radical cations because the former gives characteristic [M − CH 2] +, [M − CH 2NCH] +, and a doubly charged ion, all of which are produced on collisional activation. Furthermore, the distonic species completely transfers CH + 2 to mroe 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 [·CH 2NH 3 +], making available a distonic species whose bimolecular reactivity can be readily investigated.
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