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The mass spectra of carboxylic acids–II: Fragmentation mechanisms in the homologous series HOOC(CH 2 ) n COOH
Author(s) -
Holmes J. L.,
St. Jean T.
Publication year - 1970
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.1210031207
Subject(s) - homologous series , fragmentation (computing) , chemistry , mass spectrum , molecule , polyatomic ion , ion , methylene , deuterium , stereochemistry , spectral line , crystallography , computational chemistry , medicinal chemistry , organic chemistry , physics , atomic physics , astronomy , computer science , operating system
The mass spectra of the homologous series of acids HOOC(CH 2 ) n COOH from n = 0 to 12 have been studied together with certain deuterium labeled members. The fragmentation mechanisms of the lower homologues are discussed in some detail. The loss of one or two molecules of water from the molecular ions was shown to proceed most favorably via a 6‐centred intermediate involving the methylene group β‐ to a carboxyl function. It was observed that the ease of carboxyl‐carboxyl interaction promoting CO 2 elimination from the molecular ion could be simply correlated with n and thus serves as a structure‐identifying feature.