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Stereospecific decompositions induced by low‐energy collision‐induced dissociation of MH + ions of epimeric alkaloids
Author(s) -
Grégoire S.,
Dugat D.,
Fournier F.,
Gramain J.C.,
Tabet J.C.
Publication year - 1995
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/rcm.1290090104
Subject(s) - chemistry , dissociation (chemistry) , ion , stereospecificity , protonation , stereochemistry , ring (chemistry) , electron ionization , mass spectrum , computational chemistry , ionization energy , yield (engineering) , ionization , photochemistry , organic chemistry , materials science , metallurgy , catalysis
Several studies have investigated stereochemical effects observed in the electron ionization and low‐energy collision‐induced dissociation (CID) mass spectra of molecular ions from synthetic and natural alkaloids. More recently, it has been shown that low‐collision‐energy CID spectra of protonated epimeric alkaloids can yield additional information. For instance, three epimeric tetracyclic alkaloids studied in the present work are characterized by different cis/trans ring junction geometries and by different configurations of the ethyl group linked to the C‐ring. Low‐energy collisional spectra of the epimeric MH + ions show large differences depending both on the ring junction geometry and the stereochemistry of the side chain. Interpretation of certain specific processes invokes ion‐dipole formation, allowing internal electron transfer. Consecutive decompositions have also been scrutinized.