
%0 Journal Article
%A Raftery, MJ 
%A Bowie, JH 
%T The Collision-Induced Dissociations of Deprotonated Amines in the Gas Phase
%J Australian Journal of Chemistry
%D 1988/09/01
%V 41
%N 9
%P 1477-1489
%K 
%R https://doi.org/10.1071/CH9881477
%U https://www.publish.csiro.au/paper/CH9881477 
%X The major collision-induced fragmentations of deprotonated primary and secondary amines are best rationalized as proceeding through the intermediacy of ion complexes. For example, the characteristic fragmentation of deprotonated ethylamine isMeCH2NH- &#8594; [Me-(CH2=NH)] &#8594; CH2N- + CH4 Secondary alkylamines behave in a similar fashion. The occurrence of proton transfer as a prelude to fragmentation is rare: the only example observed in this study is the probable reaction PhNEt &#8594;&#8594; PhNHCHMe &#8594; [(PhNH=CH)Me-] &#8594; C7H6N- + CH4 which is preceded or accompanied by proton transfer between the methylene and phenyl substituents. Deprotonated aniline undergoes specific elimination of CNH from the 1-position to form the cyclopentadienyl anion. Finally, retro reactions are observed for the piperazine anion, e.g. HN(CH2CH2)2N &#8594; -CH2CH2N=CH2+CH2NH 
