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, [online], https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=907083 (Accessed May 26, 2026)
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Electron Ionization Mass Spectra of Alkylated Sulfabenzamides
Published
Author(s)
, , Roman S. Borisov, Dmitry I. Zhilyaev, Vladimir G. Zaikin, ,
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
Pub Type
Journals
Download Paper
Keywords
Mass Spectrometry, Reaction Mechanisms, Derivatization, Alkylation, Sulfabenzamide
Citation
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Created March 30, 2011, Updated May 7, 2026