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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 6
BKCSDE 12(6)
June 20, 1991 

 
Title
Theoretical Studies on the Gas-Phase Nucleophilic Aromatic Substitution Reaction
Author
Ikchoon Lee*, Hyoung Yeon Park, Bon-Su Lee
Keywords
Abstract
The gas-phase nucleophilic substitution reaction of pentafluoroanisole with OH- and NH2- nucleophiles have been studied theoretically using the AM1 method. Three reaction channels, SN2, IPSO and SNAr (scheme 1), are all very exothermic so that all are accessible despite the varying central energy barriers which are much lower than the reactants level. In the IPSO and SNAr channels, the reactants form directly a stable σ -anion complex which proceedsto form a proton transfer complex via a transition barrier corresponding to a loose π-type complex with the F-(or OCH3-) leaving group. Due to a greater number of probable reaction sites available for SNAr compared to the other two processes, the SNAr channel is favored as experimentally observed.
Page
658 - 661
Full Text
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