Electrostatic effects in N-heterocyclic carbene catalysis: Revealing the nature of catalysed decarboxylation

Zhipeng Pei, Qinyu Qiao, Cunxi Gong, Donghui Wei, Michelle L. Coote

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Quantum chemistry is used to investigate the nature of protonated N-heterocyclic carbene (NHC·H+) catalysed decarboxylation recently reported by Zhang et al. (ACS Catal., 2021, 11, 3443-3454). Our results show that there are strong electrostatic effects within the NHC·H+ catalysed decarboxylation, and these dominate hydrogen bonding. At the same time, energy decomposition analyses and comparison between the original NHC·H+ catalyst and a truncated form reveal that stabilizing dispersion interactions are also critical, as is induction. We also show that the electrostatic effects and their associated catalytic effects can be further enhanced using charged functional groups.

Original languageEnglish
Pages (from-to)24627-24633
Number of pages7
JournalPhysical Chemistry Chemical Physics
Volume23
Issue number43
DOIs
Publication statusPublished - 2021
Externally publishedYes

Keywords

  • Electrostatic
  • N-heterocyclic
  • carbene
  • catalysis
  • decarboxylation
  • chemistry

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