Electrostatic effects in N-heterocyclic carbene catalysis: revealing the nature of catalysed decarboxylation†
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.
- This article is part of the themed collections: New Perspectives on Molecular Simulation of Chemistry and Physics in External Electric Fields and 2021 PCCP HOT Articles