Mass spectrometry of condensed  N ‐heterocycles: II—A novel  ortho  effect in the electron impact induced fragmentation of some  C ‐(2‐nitrophenyl)‐azoles and ‐azoloazines | Zendy

Könnecke A. | Zendy; Lepom P. | Zendy; Dörre R. | Zendy; Lippmann E. | Zendy; Herzschuh R. | Zendy; Kralj B. | Zendy; Stanovnik B. | Zendy; Tišler M. | Zendy

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Mass spectrometry of condensed N ‐heterocycles: II—A novel ortho effect in the electron impact induced fragmentation of some C ‐(2‐nitrophenyl)‐azoles and ‐azoloazines

Author(s) -

Könnecke A.,

Lepom P.,

Dörre R.,

Lippmann E.,

Herzschuh R.,

Kralj B.,

Stanovnik B.,

Tišler M.

Publication year - 1980

Publication title -

organic mass spectrometry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.475

H-Index - 121

eISSN - 1096-9888

pISSN - 0030-493X

DOI - 10.1002/oms.1210150204

Subject(s) - isomerization , chemistry , moiety , fragmentation (computing) , ion , imine , mass spectrometry , photochemistry , electron transfer , electron ionization , nitro , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , ionization , catalysis , alkyl , chromatography , computer science , operating system

Heterocycles containing an integrated 2‐nitrobenzaldehyde imine moiety produce ions of m/z 134 with high abundance under electron impact. As shown by kinetic energy release measurements these ions have the same structure in all the cases studied, identical to m/z 134 formed from the reference compound 2‐nitrobenzoylpiperidide. The mechanism of formation of m/z 134 most probably involves isomerization of its precursor ion to give a spiro intermediate, from which m/z 134 arises either synchronously or after a second isomerization. Both alternatives formally represent an oxygen transfer from the nitro group to the imino carbon via a 5‐membered transition state.

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