Journal of Organic Chemistry p. 7602 - 7608 (1994)
Update date:2022-08-28
Topics:
Tee, Oswald S.
Mazza, Charles
Lozano-Hemmer, Rafael
Giorgi, Javier B.
The effects of DMSO on the kinetics of cleavage of m- and p-nitrophenyl alkanoates (mNPAlk and pNPAlk) by α- and β-cyclodextrin (α-CD and β-CD) in basic aqueous solution have been studied.For the two acetates addition of up to 60percent (v/v) of DMSO increases rates but overall it has little effect on substrate binding, transition state binding, or the acceleration due to complexation.By contrast, in 50percent (v/v) aqueous DMF these characteristics are greatly affected such that the normal difference in reactivity of the isomers is almost removed.The cleavage of mNPAlk and pNPAlk (C2 to C10) by the CDs in 60percent (v/v) aqueous DMSO have very different chain length dependences for substrate binding and transition state binding, and there are significant changes from their behavior in water.Even though hydrophobic effects seem to be largely removed in 60percent aqueous DMSO, and the difference between the reactivities of the isomers is reduced, reaction of mNPAlk proceeds through aryl group inclusion and that of pNPAlk through acyl group inclusion, as in water.The cleavage of m-tert-butylphenyl acetate is accelerated more in 60percent (v/v) aqueous DMSO than in water because the solvent change weakens substrate binding more than transition state binding.
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