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Substituent Effects on the Nonradical Reactivity of 4-Dehydropyridinium Cation
Recent studies have shown that the reactivity of the
4-dehydropyridinium
cation significantly differs from the reactivities of its isomers
toward tetrahydrofuran. While only hydrogen atom abstraction was observed
for the 2- and 3-dehydropyridinium cations, nonradical reactions were
observed for the 4-isomer. In order to learn more about these reactions,
the gas-phase reactivities of the 4-dehydropyridinium cation and several
of its derivatives toward tetrahydrofuran were investigated in a Fourier
transform ion electron resonance mass spectrometer. Both radical and nonradical
reactions were observed for most of these positively charged radicals.
The major parameter determining whether nonradical reactions occur
was found to be the electron affinity of the radicalsî—¸only
those with relatively high electron affinities underwent nonradical
reactions. The reactivities of the monoradicals are also affected
by hydrogen bonding and steric effects