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Electron Ionization Mass Spectra of Alkylated Sulfabenzamides



Nino G. Todua, Kirill V. Tretyakov, Roman S. Borisov, Dmitry I. Zhilyaev, Vladimir G. Zaikin, Stephen E. Stein, Anzor I. Mikaia


Mono-, di- and trialkyl derivatives of "sulfabenzamide" (N-4-aminophenylsulfonyl-benzamide) are prepared and their EI mass spectra are examined. It is found that the fragmentation of N- alkylsulfabenzamides (Alkyl = CH3 to n-C5H11) proceeds via a very specific rearrangement process involving migration of carbonyl O-atom to sulfur. The proposed mechanism involves an intermediate formation of distonic molecular ions, and the driving force for this process is the formation of stable N-alkylcyanobenzene cations [R-N+≡CC6H5]. The findings are confirmed by exact mass measurement, MS/MS experiments and deuterium labeling.
Rapid Communications in Mass Spectrometry


Mass Spectrometry, Reaction Mechanisms, Derivatization, Alkylation, Sulfabenzamide


Todua, N. , Tretyakov, K. , Borisov, R. , Zhilyaev, D. , Zaikin, V. , Stein, S. and Mikaia, A. (2011), Electron Ionization Mass Spectra of Alkylated Sulfabenzamides, Rapid Communications in Mass Spectrometry (Accessed April 18, 2024)
Created March 30, 2011, Updated February 19, 2017