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Gas‐phase deprotonation of arylalkylamines. A collision‐induced dissociation study
Author(s) -
Cardoso Ana M.,
Alexandre Sílvia M. G.,
Barros Cristina M. F.,
Correia A. J. Ferrer,
Nibbering Nico M. M.
Publication year - 1999
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19991015)13:19<1885::aid-rcm716>3.0.co;2-k
Subject(s) - chemistry , deprotonation , dissociation (chemistry) , collision induced dissociation , mass spectrum , molecule , ionization , fragmentation (computing) , ion , ring (chemistry) , mass spectrometry , chemical ionization , reagent , medicinal chemistry , stereochemistry , photochemistry , tandem mass spectrometry , organic chemistry , chromatography , computer science , operating system
The collision‐induced dissociation (CID) of deprotonated arylalkylamines of general formula R 1 C 6 H 4 CHR 2 CH 2 NR 3 2 (where R 1 = H, OH, F or NO 2 ; R 2 = H or OH; R 3 = H or CH 3 ) generated by negative chemical ionization with H 2 O and D 2 O as ionizing reagents, is discussed. The negative chemical ionization mass spectra show that, in the absence of a hydroxy group in the aromatic ring, deprotonation takes place at the benzylic position whereas the proton is lost from the OH group when present. The nitro compound forms only M −· ions. The CID spectra of the deprotonated molecules show that fragmentations are strongly dependent on the structural features of the molecules, namely the presence or absence of substituents in the aromatic ring or aliphatic chain. Copyright © 1999 John Wiley & Sons, Ltd.