Collect. Czech. Chem. Commun. 1980, 45, 1928-1936

The Ritter reaction of the acrylonitrile oligomer

Václav Janout and Pavel Čefelín

Institute of Macromolecular Chemistry, Czechoslovak Academy of Sciences, 162 06 Prague 6


The Ritter reaction of oligomeric models of poly(acrylonitrile) with tert-butyl alcohol in tetramethylene sulphone leads to the respective N-tert-butylamides and proceeds via the second-order kinetics. The rate constants increase only little on passing from the monomeric to the trimeric model. The decrease in the activation enthalpy ΔH is almost compensated for by the decrease in the activation entropy parameter. No effect of the neighbouring functional group on the reaction kinetics could be observed. A new conformational equilibrium is established during the reaction.