Acid-base equilibria and decomposition of secondary (N-Cl)-α-amino acids

Article abstract of DOI:10.1016/S0040-4020(01)89591-0

The decomposition of (N-Cl)-Sarcosine, (N-Cl),(N-Me)-Alanine, (N-Cl)- Proline, (N-Cl),(N-Me)-Valine, and (N-Cl)-2-piperidine carboxylic acid (Pipecolic acid) was studied under acid conditions. The results suggest the participation of the four possible species of the (N-Cl)-α-amino acid. A reaction mechanism is proposed which allows us to estimate the rate constant for the decomposition of each species, as well as the yet unknown macroscopic, microscopic and tautomeric equilibrium constants. The relation between the different rate and equilibrium constants is also analyzed.