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Unusual cross‐ring S N 2 reactions of [MH] − ions of methoxyacetanilides
Author(s) -
Blanksby Stephen J.,
Dua Suresh,
Bowie John H.
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.1290090214
Subject(s) - chemistry , ion , ring (chemistry) , mass spectrum , deprotonation , tandem , analytical chemistry (journal) , medicinal chemistry , organic chemistry , materials science , composite material
Deprotonated o, m ‐, and p ‐methoxyacetanilide show pronounced peaks in their collision‐induced tandem mass spectra (MS/MS) produced by losses of the elements of C 2 H 6 . It is proposed that this reaction is a ‘cross‐ring’ internal S N 2 reaction involving an incipient methyl anion. For example, p ‐CH 3 OC 6 H 4 − COCH 3 → [( p ‐CH 3 OC 6 H 4 NCO)CH 3 − ]→ − OC 6 H 4 NCO+C 2 H 6 .