Abstract
In this work, a MEDT study is carried out on the dehydration of 2-(hydroxy(phenyl)methyl)phenol HPMP to the corresponding ortho-quinone methide OQM experimentally reported by Tang and coworkers. Both catalyzed and uncatalyzed reactions were studied and it was found that Sc(OTf)3 reduces considerably the activation barriers. The catalyzed reaction takes place initially by the formation of a stable molecular complex between the Sc(OTf)3 Lewis acid and HPMP. The structure of this complex was studied by using MEP map, IGMH and QTAIM analyses and it was found an ionic interaction between the Sc atom and the oxygen atom of HPMP. The electron transfer calculations indicated that the catalyzed reaction is highly polar which is probably responsible for the significant reduction of the activation barriers and consequently performing of the reaction at room temperature under experimental conditions. Finally, the molecular mechanism of the reaction was investigated by ELF analysis and it was concluded that the cleavage of the C4-O5 bond is taken place by polarization of the bonding electron toward the O5 oxygen atom in the first half of the reaction.
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