Can electrostatic catalysis of Diels-Alder reactions be harnessed with pH-switchable charged functional groups?
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]
|Collections||ANU Research Publications|
|Source:||Physical Chemistry Chemical Physics|
|Access Rights:||Open Access|
|PCCP-DielsAlder_unformatted.pdf||381.63 kB||Adobe PDF|
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