.Frequency analysis was done to check the structure is stable substance or transition state. In the experimental work, Clayden et al. used the substrates of both configurations of the carbonyl α-position to obtain the product. S1 and S2 (Fig. )may have similar mechanisms due to a shared aromatic nucleophilic substitution reaction. So in order to directly compare with the experimental linear free energy relationship, the conditions used in the calculation of the linear free energy relationship will be consistent when the linear free energy relationship is determined(S2, 5equiv LDA/THF/-20℃), but the reaction of S1 will be calculated to establish the mechanism framework to verify the available of the reaction(the extraction of proton in S1 is more difficult). For the enol lithium intermediate A obtained by deprotonation, the protonated amine in the structure can be substituted with THF to obtain another enol intermediate B. This process is greatly exothermic. After that, the enol lithium moiety in the intermediate B nucleophilic attack on the benzene ring moiety in the molecule, this step is the final step of the aromatic nucleophilic substitution process, and its energy barrier is 10.62 kcal/mol. After many attempts, we found that the corresponding Meisenheimer intermediates and dissociation transition states could not be optimized, which led us to speculate that this aromatic nucleophilic substitution reaction is likely to be a concerted mechanism with a dynamic intermediate. The results of the IRC calculations confirm the existence of dynamic intermediate which is consistent with the experimental facts reported by Clayden et al. that the Meisenheimer intermediates that are unable to intercept this reaction(Fig. ). In the reaction involving KHMDS, the aromatic nucleophilic substitution reaction is carried out stepwise, which is a typical addition-elimination mechanism, and addition as a rate-determining step.