Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Collision-Induced Dissociations of Deprotonated Amines in the Gas Phase

MJ Raftery and JH Bowie

Australian Journal of Chemistry 41(9) 1477 - 1489
Published: 1988

Abstract

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 is

MeCH2NH- → [Me-(CH2=NH)] → 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 →→ PhNHCHMe → [(PhNH=CH)Me-] → 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 → -CH2CH2N=CH2+CH2NH

https://doi.org/10.1071/CH9881477

© CSIRO 1988

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions