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Can electrostatic catalysis of Diels-Alder reactions be harnessed with pH-switchable charged functional groups?

Aitken, Heather; Coote, Michelle

Description

Quantum-chemical calculations at the M06-2X/6-31+G(d,p) and G3(MP2)CC levels of theory are used to assess the feasibility of harnessing charged functional groups to electrostatically catalyse Diels–Alder reactions and alter their regio selectivity. For the reaction of the polar diene 2-pyrone with substituted cyclopentene, pH switches of nearly 60 kJ mol−1 are observed in the gas-phase. To switch regioselectivity however it is necessary to toggle between negatively and positively charged...[Show more]

CollectionsANU Research Publications
Date published: 2018
Type: Journal article
URI: http://hdl.handle.net/1885/160871
Source: Physical Chemistry Chemical Physics
DOI: 10.1039/c7cp07562f
Access Rights: Open Access

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