title: Electron ionization mass spectra of alkylated sulfabenzamides.
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.
authors.affiliation: National Institute of Standards and Technology, Gaithersburg, MD 20899-8320, USA. nino.todua@nist.gov
authors.forename: Nino G
authors.initials: NG
authors.lastname: Todua
authors.forename: Kirill V
authors.initials: KV
authors.lastname: Tretyakov
authors.forename: Roman S
authors.initials: RS
authors.lastname: Borisov
authors.forename: Dmitry I
authors.initials: DI
authors.lastname: Zhilyaev
authors.forename: Vladimir G
authors.initials: VG
authors.lastname: Zaikin
authors.forename: Stephen E
authors.initials: SE
authors.lastname: Stein
authors.forename: Anzor I
authors.initials: AI
authors.lastname: Mikaia
mesh_terms: D000478:Alkylation; D008970:Molecular Weight; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013449:Sulfonamides / Q000737:chemistry; D053719:Tandem Mass Spectrometry
chemical_list: D013449:Sulfonamides; C034094:sulfabenzamide