Kinetics and mechanisms of the diels-alder reaction of 9-bromomethyl anthracene with citraconic anhydride: A DFT study

Abstract

In this work, the kinetics and mechanism of the Diels-Alder cycloaddition reaction between the 9-bromomethyl antracene and Citraconic anhydride dienophile have been investigated theoretically in the toluene solution. All of the calculations have been performed by using the valuable DFT methods and PCM model.The reaction can be progressed via two different pathways, I and II. In the structure of the reactants of the pathways I and II, the 9-bromomethyl antracene and Citraconic anhydride species have different orientations. Both of the pathways have been investigated in details. The obtained DFT-resultssuch as prediction of the major product of the reaction are in agreement with the experimental results, confirming validity of the DFT-proposed mechanism.