Electron Ionization Mass Spectra of Alkylated Sulfabenzamides

Published

March 30, 2011

Author(s)

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

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

Keywords

Mass Spectrometry, Reaction Mechanisms, Derivatization, Alkylation, Sulfabenzamide

Citation

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 October 8, 2025)