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Gas‐phase fragmentation of protonated benzodiazepines
Author(s) -
Risoli Antonella,
Cheng Joey B. Y.,
Verkerk Udo H.,
Zhao Junfang,
Ragno Gaetano,
Hopkinson Alan C.,
Siu K. W. Michael
Publication year - 2007
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/rcm.3084
Subject(s) - chemistry , benzonitrile , protonation , benzene , fragmentation (computing) , ionic bonding , ammonia , photochemistry , gas phase , ion , medicinal chemistry , organic chemistry , computer science , operating system
Abstract Protonated 1,4‐benzodiazepines dissociate in the gas phase by the common pathway of CO elimination and by unique pathways dictated by the substituents; the latter typically differentiate one benzodiazepine from another. Protonated 3‐dihydro‐5‐phenyl‐1,4‐benzodiazepin‐2‐one, the base diazepam devoid of substituents, dissociates by eliminating CO, HNCO, benzene, and benzonitrile. Mechanisms of these reactions are proposed with ionic products being resonance stabilized. The abundant [MH−CO] + ion dissociates to secondary products via elimination of benzene, benzonitrile, the NH 2 radical, and ammonia, yielding again ionic products that are stabilized by resonance. Copyright © 2007 John Wiley & Sons, Ltd.