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Electron‐impact studies. LXXXVII — ortho effects in the negative ion mass spectra of salicylates and anthranilates
Author(s) -
Bowie J. H.,
Ho A. C.
Publication year - 1974
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.1210091007
Subject(s) - mass spectrum , chemistry , cleavage (geology) , ion , nitro , electron ionization , medicinal chemistry , polyatomic ion , molecular mass , mass spectrometry , organic chemistry , chromatography , ionization , materials science , alkyl , fracture (geology) , composite material , enzyme
Abstract The molecular anions of the methyl and phenyl esters of 4‐nitrosalicylic acid and 5‐nitroanthranilic acid eliminate ROH (R Me or Ph) by an ortho rearrangement. The molecular anions of phenyl 3‐hydroxy‐5‐nitrobenzoate and phenyl 3‐amino‐5‐nitrobenzoate lose PhOH to a lesser extent, and a study of the pressure dependence of these eliminations indicates the operation of simultaneous two‐stage cleavage reactions. The competitive ortho effects observed when the nitro group is adjacent to either the ester or hydroxyl functions are described.