Functional Group Interactions During the Decarboxylation of Aliphatic Carboxylic Anions: a Study by MS/MS and DFT Computations

摘要

1. Decarboxylation is the primary fragmentation of N-benzoylamino acid anions. 2. DFT calculations indicate that decarboxylation is accompanied by proton migration, yielding the lowest energy product anion. 3. The mechanism of decarboxylation varies with the spacing between the amide and carboxyl functional groups. 4. For N-benzoyl-α-amino acids, the amide oxygen participates in proton transfer. 5. For longer-chain N-benzoyl-ω-amino acids, the amide nitrogen participates in proton transfer.