Investigation of the gas-phase reactions of 2-methoxypropene with protonated pyridine- and aniline- based compounds

The purpose of this thesis research was to examine the gas-phase reactions of 2- methoxypropene (MOP) with protonated nitrogen-containing compounds, specifically pyridine, and aniline derivatives, in a linear quadrupole ion trap mass spectrometer. In addition, to maintain consistency with past experiments, several previously investigated sulfoxides were included in this study. The analytes were protonated via atmospheric pressure chemical ionization (APCI) in a linear quadrupole ion trap spectrometer, transferred into the ion trap, isolated, and then allowed to react with MOP inside the ion trap. 

All the protonated sulfoxides examined reacted with MOP to generate a stable adduct, as expected. They also transferred a proton to MOP. All protonated anilines reacted in the same manner with MOP. The diagnostic adduct formation reaction is proposed to involve proton transfer from the protonated analyte to MOP followed by addition of the neutral analyte to protonated MOP. In sharp contrast to sulfoxides and anilines, protonated pyridines were unreactive toward MOP. Therefore, the formation of a stable adduct is diagnostic for both sulfoxides and anilines but these compounds can be differentiated from pyridines due to the lack of reactivity of their protonated forms toward MOP.