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

Maocai Yan,Zhen Zhang,Jinhui Zhou,Wei Li,Chunyan Zhang,Shuai Fan,Zhaoyong Yang

doi:10.1016/j.dib.2019.104110

Abstract

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. 1H and 13C 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.

Highlights

density functional theory (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
Chemistry Theoretical chemistry, organic chemistry, reaction mechanism Coordinate, Figure DFT calculation (Gaussian 09, Gaussian Inc.), NMR (Bruker Avance III-400 and AscendTM 600 spectrometers) Raw, analyzed Synthesized samples were dissolved in CDCl3 or DMSO-d6 before NMR determination DFT calculations at M06-2X/6-31þG** level; NMR spectra detected on Bruker Avance III-400 or AscendTM 600 spectrometers School of Pharmacy, Jining Medical University, Rizhao, Shandong, 276800, China Data is with this article Yan, M.; Zhang, Z.; Zhou, J.; Li, W.; Zhang, C.; Zhang, J.; Wang, H.; Yang, X.; Fan, S.; Yang, Z

Summary

Data Article

Maocai Yan a, *, Zhen Zhang a, Jinhui Zhou a, Wei Li a, Chunyan Zhang a, Shuai Fan b, Zhaoyong Yang b, **. Maleimide ring is an important scaffold in organic chemistry, and tosyloxy group is a functional group widely used in organic synthesis. 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 6-31þG** 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.

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