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To elucidate the selectivity of methylene substitution reactions of monosubstituted and disubstituted oxyaromatic compounds in a low pressure quadrupole ion trap environment, the relative abundances of covalently bound and loosely bound adducts formed by ion/molecule reactions with ethylene (ET), ethylene oxide (ETOX), and dimethyl ether (DME) were compared. Adduct ions of all three reagent gases were formed in both a conventional ion source and a quadrupole ion trap and characterized by collisionally activated dissociation. For DME and ET, the covalently bound adducts formed at (M + 45)(+) and (M + 41)(+), respectively, are direct precursors to the methylene substitution product ions at (M + 13)(+). ETOX and ET do not demonstrate the same functional group selectivity for methylene substitution as previously observed for DME. This is attributed to differences in reaction exothermicities and competing reactions.

Methylene substitution reactions in a quadrupole ion trap selectivity of ethylene, ethylene oxide, and dimethyl ether reactive ions