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  • Title: Mechanism study of SO2 elimination from sulfonamides by negative electrospray ionization mass spectrometry.
    Author: Hu N, Liu P, Jiang K, Zhou Y, Pan Y.
    Journal: Rapid Commun Mass Spectrom; 2008 Sep; 22(17):2715-22. PubMed ID: 18668633.
    Abstract:
    The elimination of SO2 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([M-H-SO2](-)/[M-H]-) values were correlated with the sigmap(-) 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 -CHCHNHSO2- structure yielded a [M-H-66](-) product ion This characteristic ion could help to distinguish the side-chain isomers.
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