Differentiation of N-from C-protonated aniline by neutralization-reionization.
Amino- and ring-protonated aniline are distinguished in the gas phase by neutralization-reionization mass spectrometry. This method takes advantage of the dramatically different stabilities and reactivities of the neutralized forms of N- and C-protonated aniline, to ascertain thereby the specific protonation site(s). Fast atom bombardment ionization of aniline is found to yield primarily the anilinium cation (N-protonated tautomer). In contrast, chemical ionization with a variety of reagent gases is shown to generate mixtures in which the ring-protonated species predominates.
Nold
M J
MJ
Department of Chemistry, University of Akron, OH 44325-3601, USA.
Wesdemiotis
C
C
D000814:Aniline Compounds / Q000737:chemistry*; D005609:Free Radicals; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D011522:Protons; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000814:Aniline Compounds; D005609:Free Radicals; D007202:Indicators and Reagents; D011522:Protons; D000644:Quaternary Ammonium Compounds