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Negative charge induced dissociation: fragmentation of deprotonated N‐benzylidene‐2‐hydroxylanilines in electrospray ionization mass spectrometry
Author(s) -
Yue Lei,
Wei Wanghui,
Dang Qiankun,
Ding Chuanfan,
Pan Yuanjiang
Publication year - 2014
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/jms.3376
Subject(s) - chemistry , fragmentation (computing) , collision induced dissociation , tandem mass spectrometry , dissociation (chemistry) , mass spectrometry , electrospray ionization , benzoxazole , ion , photochemistry , mass spectrum , benzonitrile , deprotonation , medicinal chemistry , organic chemistry , chromatography , computer science , operating system
Unimolecular reactivities of different N‐benzylidene‐2‐hydroxylaniline anions were investigated in gas phase by electrospray ionization tandem mass spectrometry. All the collision‐induced dissociation spectra of N‐benzylidene‐2‐hydroxylaniline anions show similar ions at phenyl anions, neutral loss of benzonitrile and benzoxazole anions, respectively. The possible fragmentation pathway was probed through deuterium labeling and various group substituents experiments. Computational results were applied to shed light on the mechanism of fragmentation patterns. The proton in the CH=N is reactive in the formation of the concerned ions. Its direct transfer to the oxygen results in 2‐hydroxyphenyl anion. Proton abstraction between benzoxazole and phenyl anion leads to the formation of benzene and benzoxazole anion. Copyright © 2014 John Wiley & Sons, Ltd.

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