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Identification of hydroxylated chlorodibenzo‐ p ‐dioxins, chlorodibenzofurans, chlorodiphenyl ethers and chloronaphthalenes as their methyl ethers by gas chromatography mass spectrometry
Author(s) -
Tulp Martin Th. M.,
Hutzinger Otto
Publication year - 1978
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200050311
Subject(s) - oxonium ion , chemistry , fragmentation (computing) , mass spectrometry , molecule , mass spectrum , methyl group , structural isomer , delocalized electron , gas chromatography , stereochemistry , ion , organic chemistry , medicinal chemistry , chromatography , group (periodic table) , computer science , operating system
The methyl ethers of a number of hydroxylated (poly)chlorodibenzo‐ p ‐dioxins, chlorodibenzofurans, chlorodiphenyl ethers and chloronaphthalenes, representing all different hydroxy substitutions, were synthesized and their mass spectra investigated. With the exception of the methoxy derivatives of the chlorodibenzofurans, it appeared that the mass fragmentation patters of the structural isomers of each class of compounds were very specifica and allowed unambiguous assignment of the position of the methoxy group in the molecule. The different fragmentation patterns can be explained in terms of plausible mechanisms resulting in stable charge delocalized (oxonium) ions. Because of its diagnostic value, this method is useful in the structure elucidation of hydroxylated metabolites of pure isomers of chlorodibenzo‐ p ‐dioxins, chlorodiphenyl ethers and chloronaphthalenes.