Ortho,Effects in organic molecules on electron impact: X—unusual ortho effects of the methyl group in o-picolinotoluidide

The mass spectrum of o-picolinotoluidide gives rise to three major fragments at m/z 184, m/z 169 and m/z 168, corresponding to the loss of CO from the molecular ion followed by the loss of ?H₂ and ?H₃ by independent pathways. It has been shown that the ortho methyl group and the nitrogen of the pyridine ring in the 2-position are involved in the formation of these three major fragments observed in the mass spectrum of o-picolinotoluidide. The mass spectrum of 2-(o-toluidino) pyridine, the molecular ion of which can resemble the M? CO]⁺ ion in o-picolinotoluidide, also shows loss of CH₃ and NH₂ radicals from the molecular ions. Based on these observations coupled with the high resolution data, the mass analysed ion kinetic energy spectrometry and high voltage scans of these fragments in both the compounds, two mechanistic pathways have been proposed for the formation of these ions in o-picolinotoluidide.