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Über die Bildung cyclischer Ionen und bicylischer Übergangszustände beim Zerfall substituierter α,ω‐Alkandiamine im Massenspektrometer. 23. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen
Author(s) -
Schöpp Emanuel,
Hesse Manfred
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590515
Subject(s) - chemistry , ketene , bicyclic molecule , fragmentation (computing) , toluene , medicinal chemistry , mass spectrum , sulfonic acid , ion , decomposition , stereochemistry , polymer chemistry , organic chemistry , computer science , operating system
Formation of cyclic ions and bicyclic transition states in the mass spectral decomposition of substituted α,ω‐alkanediamines. N‐Phenethyl‐N(4‐acetamidobutyl)‐ p ‐toluene‐sulfonamide ( 4 ) and its homologues were synthesized and the mass spectral behaviour investigated. After loss of a benzyl radical from the molecular ion two different fragmentation reactions are observed. The lower homologous members – namely compounds 1 , 2 and 3 – lose ketene by formation of cyclic ions ( Scheme 1 ). The higher homologues of this series of compounds ( 4 , 5 , 6 ) show a pronounced (to 18% ∑ 50 ) loss of p ‐toluene sulfonic acid. This decomposition reaction proceeds presumably through a bicyclic transition state ( Scheme 3 ).