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Acceleration of Thiol Ester Hydrolysis by Cyclodextrins: Evidence from Rate and Computational Studies
Author(s) -
Annalakshmi Subramanian,
Pitchumani Kasi
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500770
Subject(s) - chemistry , hydrolysis , thiol , cyclodextrin , covalent bond , molecular dynamics , alkaline hydrolysis , catalysis , acceleration , organic chemistry , computational chemistry , combinatorial chemistry , physics , classical mechanics
Hydrolysis of diaryl thiol esters with different substituents is studied in the presence of cyclodextrins under alkaline conditions. The presence of cyclodextrin enhances the rate of hydrolysis significantly and covalent catalysis by secondary hydroxy groups of cyclodextrin is proposed. The observed results and the proposed model find support in molecular dynamics simulations and free energy calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)