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Formation of benzimidazole derivatives during electron ionization induced fragmentation and pyrolysis of N ‐benzyl‐ o ‐nitroaniline
Author(s) -
Danikiewicz Witold
Publication year - 1998
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19980615)12:11<689::aid-rcm219>3.0.co;2-2
Subject(s) - chemistry , fragmentation (computing) , pyrolysis , ionization , decomposition , pyrolytic carbon , electron ionization , benzimidazole , nitroaniline , medicinal chemistry , photochemistry , organic chemistry , ion , computer science , operating system
Decomposition of N ‐benzyl‐ o ‐nitroaniline during pyrolysis and upon electron ionization has been studied. Pyrolysis of N ‐benzyl‐ o ‐nitroaniline starts above 450 °C and yields 2‐phenylbenzimidazole and 1‐phenyl‐1,3‐dihydrobenzimidazol‐2‐one as the main products. Upon electron ionization N ‐benzyl‐ o ‐nitroaniline undergoes several fragmentations, the most important being eliminations of H 2 O, OH · and HO 2 · . All of these processes are the examples of different ortho ‐effects. Elimination of H 2 O leads mainly to the formation of 1‐phenyl‐1,3‐dihydrobenzimidazol‐2‐one, similar to the pyrolytic decomposition. Reaction mechanisms for the main fragmentation processes are discussed. © 1998 John Wiley & Sons, Ltd.