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Effect of alkali metal cationization on the collision‐induced decomposition of alkyl per‐ O ‐acetyl‐2‐deoxy‐2‐halo‐α‐ O ‐mannopyranosides
Author(s) -
Madhusudanan K. P.,
Rani A.,
Kumar B.,
Suryawanshi S. N.
Publication year - 1993
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.1210280812
Subject(s) - chemistry , alkali metal , fragmentation (computing) , alkyl , medicinal chemistry , decomposition , substituent , metal , ion , stereochemistry , inorganic chemistry , organic chemistry , computer science , operating system
Abstract The effect of alkali metal cationization on the collision‐induced decomposition of alkyl per‐ O ‐acetyl‐2‐deoxy‐2‐bromo‐and‐iodo‐α‐ O ‐mannopyranosides was studied. The bromo sugars gave fairly abundant MH + , whereas for the iodo sugars the MH + ions were insignificant. However, both the bromo and the iodo derivatives gave abundant M + alkali metal ion complexes. In contrast to the behaviour of the MH + ion, the [M + Li] + , [M + Na] + and [M + K] + ions of these compounds do not decompose by loss of the C(1) substituent. Elimination of AcOH is the preferred fragmentation pathway of [M + Cat] + . Elimination of HX occurs only after loss of AcOH and CH 2 CO from MH + , whereas [M + Cat] + directly loses HX. The elimination of HX is more pronounced from [M + Na] + and [M + K] + than from [M + Li] + . Loss of AcOLi is an additional fragmentation route observed in the case of the decomposition of [M + Li] + ion.