
%0 Journal Article
%A Bowie, JH 
%A Stringer, MB 
%A Duus, F 
%A Lawesson, S 
%A Larsson, FCV 
%A Madsen, J+ 
%T Fragmentations of organic negative ions. Mercapto acids and esters. A reinvestigation
%J Australian Journal of Chemistry
%D 1984/08/01
%V 37
%N 8
%P 1619-1624
%K 
%R https://doi.org/10.1071/CH9841619
%U https://www.publish.csiro.au/paper/CH9841619 
%X Thioglycollates and &#946;-thiopropionates with SH and/or CO2H groups yield pronounced (M-H)- ions in their negative ion spectra, not molecular negative ions as we previously reported. Compounds containing R1-S-CH2- functionality (R1 = alkyl or aryl) undergo &#945; cleavage to S to yield R1S- and -S-CH2-ions. Hydrogen rearrangements are rare but thioglycollates R1SCH2CO2H characteristically eliminate R1SH to yield CH2CO2-. Fragment negative ions generally do not contain enough excess energy to allow decomposition, so we have studied their collision induced dissociations. Simple cleavage reactions are usual: for example BuSCH2CO2- decomposes to yield both BuS- and BuSCH2-. Group migration to sulfur is also observed; for example, ions -SCH2CO2R2 (R2 = alkyl or aryl) eliminate carbon dioxide to produce R2SCH2- as the major product. 
