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Anionic Migration Reactions in Aromatic Systems Effected by Collisional Activation. Deprotonated Anilides Containing Methoxycarbonyl Substituents
Author(s) -
Blanksby Stephen J.,
Dua Suresh,
Christie Hamish,
Bowie John H.
Publication year - 1996
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/(sici)1097-0231(19960315)10:4<478::aid-rcm514>3.0.co;2-a
Subject(s) - chemistry , deprotonation , moiety , radical , ring (chemistry) , amide , hydrogen atom , medicinal chemistry , mass spectrum , molecule , ion , stereochemistry , computational chemistry , organic chemistry , group (periodic table)
Long‐range cross‐ring reactions are of minor importance in the collision‐induced mass spectra (MS/MS) of [M−H] − ions of CH 3 OCO‐C 6 H 4 ‐NHCOR systems: e.g. the loss of "CD 3 CO 2 CH 3 ' from CH 3 OCO–C 6 H 4 –ÑCOCD 3 . Major processes involve (i) losses of radicals to form stable radical anions, e.g. loss of a ring hydrogen atom and losses from the ester (CH 3 ·, CH 3 O · and · CO 2 CH 3 ), (ii) losses of neutral molecules from the amide moiety [e.g. CO (R=H) and CH 2 CO (R=CH 3 )], and proximity effects when the two substituents are ortho [e.g. loss of (CH 3 OD+CO 2 ) from o ‐CH 3 OCO‐C 6 H 4 ÑCOCD 3 ].