Polymerization of N-carboxy-amino acid anhydrides in the solid state. I. Polymerizability of the various α-amino acid NCAs in the solid state

The solid-state polymerization of various α-amino acid NCAs was investigated and the results were compared with those obtained by heterogeneous polymerization in acetonitrile. Essential differences were found in the polymerizability of the NCAs in these two systems. In the solid state, L-leucine NCA was the most reactive among the NCAs examined, and its reactivity was even higher than in the precipitation polymerization of acetonitrile solutions. On the other hand, glycine NCA was the most inert among the NCAs examined in the solid state. The difference between the reactivities of glycine NCA and L-alanine NCA was interpreted in terms of their crystal structures. Several kinetic features of the solid-state polymerization were studied on γ-benzyl-L -glutamate NCA.