Volume 7 Issue 4
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Cheng Cai, Weiqiang Tang, Chongzhi Qiao, Bo Bao, Peng Xie, Shuangliang Zhao, Honglai Liu. A reaction density functional theory study of solvent effect in the nucleophilic addition reactions in aqueous solution. Green Energy&Environment, 2022, 7(4): 782-791. doi: 10.1016/j.gee.2020.11.028
Citation: Cheng Cai, Weiqiang Tang, Chongzhi Qiao, Bo Bao, Peng Xie, Shuangliang Zhao, Honglai Liu. A reaction density functional theory study of solvent effect in the nucleophilic addition reactions in aqueous solution. Green Energy&Environment, 2022, 7(4): 782-791. doi: 10.1016/j.gee.2020.11.028
shu

A reaction density functional theory study of solvent effect in the nucleophilic addition reactions in aqueous solution

doi: 10.1016/j.gee.2020.11.028

  • a State Key Laboratory of Chemical Engineering and School of Chemical Engineering, East China University of Science and Technology, Shanghai, 200237, China;

  • b School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China;

  • c Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004, China

Funds:

This work is supported by National Natural Science Foundation of China (Nos. 91934302, 21878078 and 21808056).

  • Received date 26 June 2020, Accepted date 26 November 2020, RevRecd date 22 September 2020, Publish date 03 December 2020,
    Abstract
  • Whereas the proper choice of reaction solvent constitutes the cornerstone of the green solvent concept, solvent effects on chemical reactions are not mechanistically well understood due to the lack of feasible molecular models. Herein, by taking the case study of nucleophilic addition reaction in aqueous solution, we extend the proposed multiscale reaction density functional theory (RxDFT) method to investigate the intrinsic free energy profile and total free energy profile, and study the solvent effect on the activation and reaction free energy for the nucleophilic addition reactions of hydroxide anion with methanal and carbon dioxide in aqueous solution. The predictions of the free energy profile in aqueous solution for these two nucleophilic addition reactions from RxDFT have a satisfactory agreement with the results from the RISM and MD-FEP simulation. Meanwhile, the solvent effect is successfully addressed by examining the difference of the free energy profile between the gas phase and aqueous phase. In addition, we investigate the solvent effect on the reactions occurred near solid-liquid interfaces. It is shown that the activation free energy is significantly depressed when reaction takes place in the region within 10 Å distance to the substrate surface owing to the decrease of hydration free energy at the solid-liquid interface.

     

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