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A mass spectrometric investigation on some 4,7‐dioxo‐4,5,6,7‐tetrahydroindole derivatives
Author(s) -
Bertazzo A.,
Ferlin M. G.,
Chiarelotto G.,
Catinella S.,
Traldi P.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300615
Subject(s) - chemistry , electron ionization , mass spectrum , ion , ionization , tautomer , metastability , fast atom bombardment , chemical ionization , spectral line , ionization energy , kinetic energy , mass spectrometry , polyatomic ion , analytical chemistry (journal) , computational chemistry , photochemistry , medicinal chemistry , organic chemistry , chromatography , quantum mechanics , astronomy , physics
The mass spectrometric behaviour of a series of 2‐aryl substituted 4,7‐dioxo‐4,5,6,7‐tetrahydroindoles has been studied in different ionization conditions (Electron Ionization and Fast Atom Bombardment), with the aid of the metastable ion studies. In electron ionization conditions all the compounds exhibit a highly favoured, primary H 2 loss giving rise to the corresponding indole‐4,7‐diones; in the usual spectra no evidence for the molecular ions in the enolic form was found, while the OH* loss observed in the MIKE (mass analyzed ion kinetic energy) spectra of molecular ions suggests that species at low internal energy content isomerize to the corresponding tautomeric enolic form. FAB mass spectra show easy formation of an unusual [M + 2H] + species, together with abundant [M + H] + and M + cations.