The role of distonic ions in the formation of CH3NH 3 (+) and (CH 3) 2NH 2 (+) from the molecular ions of octopamine and synephrine.

ABSTRACT

It is shown by mass-analyzed ion kinetic energy spectrometry that the metastably decomposing molecular ions of octopamine (p-HOC6H4CH(OH)CH2NH2) and synephrine (p-HOC6H4CH(OH)CH2NHCH3) yield only protonated methylamine and dimethylamine, respectively, as product ions. From deuterium labeling and variation of the internal energy of the molecular ions, experimental support has been obtained that these product ions are generated via the occurrence of a distonic ion-neutral complex. In the case of octopamine, this complex would consist of a nitrogen-protonated aminomethyl radical and p-hydroxylbenzaldehyde in which the former species abstracts the aldehydic or phenolic hydrogen atom from the latter to give protonated dimethylamine.