DFT calculation and NMR data of novel aryloxymaleimides and the intermediates and transition states in the reaction

Maleimide ring is an important scaffold in organic chemistry, and tosyloxy group is a functional group widely used in organic synthesis. Nevertheless, tosyloxymaleimide compounds have been rarely reported, and the reactivity properties and potential applications of tosyloxymaleimide in organic synthesis remain to be explored. This article presents the density functional theory (DFT) calculation data of the reaction mechanism of nucleophilic substitutions of tosyloxymaleimide with phenol, including the coordinate of all the stationary points (the reactant, transition states, intermediates, and product). All the structures had been geometrically optimized using M06-2X functional and 6-31+G** basis set; the reactant, intermediates and product had no imaginary frequencies, and each transition state has only one imaginary frequency in the vibration analysis at the same computation level. The intrinsic reaction coordinates (IRCs) of two steps of the reaction were calculated. (1)H and (13)C NMR spectra of the novel aryloxymaleimide compounds synthesized using this nucleophilic substitution reaction (doi: 10.1016/j.molstruc.2019.04.020 Yan et al.,) were also presented in this article.