Theoretical study on the ring-opening hydrolysis reactions of N-alkylmaleimide dimers

摘要

On the basis of our previous experimental results, the ring-opening hydrolysis reaction mechanisms of two kinds of N-alkylmaleimide dimers without or with the assistance of one and two water molecules have been theoretically investigated in detail. All possible geometries were optimized using the B3LY P/6-311+G(d, p)//B3LYP/6-31+G(d) method in the gas phase and ethanol solution. Calculated results show that every pathway is a four-step hydrolytic degradation process and every step could occur in a concerted way, instead of previously suggested asynchronous stepwise mechanism. Extra H2O or ethanol could act as carriers of proton. The results are consistent with experimental observations. (C) 2017 Elsevier B.V. All rights reserved.