Hydrolytic degradation of N,N′-ethylenedimaleimide: Crystal structures of key intermediates and proposed mechanisms

• Five single-crystal structures have been investigated; molecular conformations and weak interactions have been analyzed.
• In compound 3, interesting 1D bowl-like zigzag chains were formed through intermolecular H-bonds.
• The hydrolytic degradation mechanisms of N,N′-ethylenedimaleimide without or with water catalysis have been proposed.

Maleimide groups are used extensively in bioconjugation reactions, but limited mechanistic studies are available regarding their hydrolysis reactions. In this paper, five single-crystal structures related with the reaction of four-step hydrolytic degradation of N,N′-ethylenedimaleimide have been investigated. On the basis of experimental results, the reaction mechanisms without or with water catalysis are proposed, which could provide some enlightenment into the study of similar hydrolytic degradations.

Five single-crystal structures related with the hydrolytic degradation of N,N′-ethylenedimaleimide have been investigated and the mechanisms without or with water catalysis have been proposed.Figure optionsDownload as PowerPoint slide