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

Literature Information

Publication Date 2021-10-26
DOI 10.1039/D1CP04444C
Impact Factor 3.676
Authors

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


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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.

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Physical Chemistry Chemical Physics
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