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Two competing ionization processes in ESI-MS analysis of N-(1,3-diphenylallyl)benzenamines: formation of the unusual [M-H] + ion versus the regular [M+H] + ion.
European Journal of Mass Spectrometry 2018 June
A series of N-(1,3-diphenylallyl)benzenamine derivatives (M) were investigated by electrospray ionization mass spectrometry in the positive-ion mode. Both the anomalous [M-H]+ and the regular [M+H]+ were observed in the ESI mass spectra. The occurrence of [M-H]+ has been supported by accurate mass spectrometry, liquid chromatography mass spectrometry, and tandem mass spectrometry analysis. Calculation results indicated that formation of [M-H]+ is attributed to the ion-molecule reaction of M with the protonated ESI solvent molecule (e.g. CH3 OH2 + ) via hydride abstraction from a tertiary Csp3 -H. The competing ionization processes leading to [M-H]+ or [M+H]+ were significantly affected by the concentration of formic acid in the electrospray ionization solvent and the proton affinity of the N atom.
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