| 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 |
