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Differentiation of N– from C–Protonated Aniline by Neutralization–Reionization
Author(s) -
Nold Michael J.,
Wesdemiotis Chrys
Publication year - 1996
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199610)31:10<1169::aid-jms405>3.0.co;2-p
Subject(s) - protonation , chemistry , aniline , tautomer , ring (chemistry) , reagent , yield (engineering) , chemical ionization , photochemistry , medicinal chemistry , ionization , organic chemistry , ion , materials science , metallurgy
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.