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Mechanism study of SO 2 elimination from sulfonamides by negative electrospray ionization mass spectrometry
Author(s) -
Hu Nan,
Liu Pengyuan,
Jiang Kezhi,
Zhou Yuping,
Pan Yuanjiang
Publication year - 2008
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.3672
Subject(s) - chemistry , fourier transform ion cyclotron resonance , deprotonation , mass spectrometry , dissociation (chemistry) , collision induced dissociation , analytical chemistry (journal) , ion , electrospray ionization , substituent , mass spectrum , fragmentation (computing) , ion cyclotron resonance , computational chemistry , stereochemistry , tandem mass spectrometry , chromatography , organic chemistry , cyclotron , computer science , operating system
The elimination of SO 2 from deprotonated sulfonamides in the negative ion mode was confirmed by Fourier transform ion cyclotron resonance mass spectrometry (FTICR‐MS) experiments. For a set of N ‐arylbenzenesulfonamides substituted at the para position of the arylamine, the ln([MHSO 2 ] − /[MH] − ) values were correlated with the σ p −substituent constants but, instead of a linear relationship, a bent line was obtained. Analyses of the complex curve led to the identification of two competing routes, which were further investigated by Hartree‐Fock theoretical calculations. Furthermore, collision‐induced dissociation (CID) of deprotonated N ‐alkylbenzenesulfonamides containing the CHCHNHSO 2 structure yielded a [MH–66] − product ion This characteristic ion could help to distinguish the side‐chain isomers. Copyright © 2008 John Wiley & Sons, Ltd.