Cyclodextrin catalysis of the smiles rearrangement of 4-nitrophenyl salicylate |
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Authors: | Katherine Yu Bezsoudnova and Anatoly K Yatsimirsky |
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Institution: | (1) Department of Chemistry, Moscow State University, 119899 Moscow, Russia;(2) Facultad de Química, Universidad Nacional Autonoma de México, 04510 México, D.F., México |
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Abstract: | α- and β-Cyclodextrins accelerate the Smiles rearrangement of 4-nitrophenyl salicylate which proceeds through the mechanism
of intramolecular aromatic nucleophilic substitution. The binding and catalytic rate constants were calculated from the dependences
of the observed pseudo-first-order rate constants of the rearrangement reaction on cyclodextrin concentration obtained at
various pH values. The catalysis was interpreted in terms of a tighter binding of the anionic, highly delocalized δ-complex
intermediate than that of the substrate to cyclodextrins. |
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Keywords: | Cyclodextrins catalysis Smiles rearrangement |
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