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Publication Citation: Electron Ionization Mass Spectra of Alkylated Sulfabenzamides

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Author(s): Nino G. Todua; Kirill V. Tretyakov; Roman S. Borisov; Dmitry I. Zhilyaev; Vladimir G. Zaikin; Stephen E. Stein; Anzor I. Mikaia;
Title: Electron Ionization Mass Spectra of Alkylated Sulfabenzamides
Published: March 30, 2011
Abstract: 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.
Citation: Rapid Communications in Mass Spectrometry
Volume: 25
Issue: 6
Pages: pp. 750 - 754
Keywords: Mass Spectrometry; Reaction Mechanisms; Derivatization; Alkylation; Sulfabenzamide
Research Areas: Mass Spectrometry