Rapid Communications in Mass Spectrometry 2011-03-30

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

Index: Rapid Commun. Mass Spectrom. 25(6) , 750-4, (2011)

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Abstract

Mono-, di- and trialkyl derivatives of 'sulfabenzamide' (N-4-aminophenylsulfonylbenzamide) have been prepared and their electron ionization (EI) mass spectra examined. It is found that the fragmentation of N-alkylsulfabenzamides (alkyl = CH(3) to n-C(5)H(11)) proceeds via a very specific rearrangement process. The proposed mechanism involves an intermediate formation of distonic molecular ions, and the driving force for this process is the formation of stable N-alkylphenylcyanide cations [R-N(+)≡CC(6)H(5)]. The findings are confirmed by exact mass measurements, tandem mass spectrometry (MS/MS) experiments and deuterium labeling.This article is a U.S. Government work and is in the public domain in the U.S.A. Published in 2011 by John Wiley & Sons, Ltd.