NDLI: Synthetic modeling of zinc thiolates: Quantitative assessment of hydrogen bonding in modulating sulfur alkylation rates

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Synthetic modeling of zinc thiolates: Quantitative assessment of hydrogen bonding in modulating sulfur alkylation rates

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Chiou, Show-jen Rheingold, Arnold L. Riordan, Charles G.
Description	Author Affiliation: Chiou SJ ( Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA.);
Abstract	A series of mononuclear zinc thiolate complexes have been prepared and fully characterized. The reactions of the complexes with alkyl halides, leading to zinc halides and the corresponding thioethers, have been examined by kinetic methods. In toluene, the reactions obey a second-order rate law displaying activation parameters consistent with a S(N)2 attack of the zinc-bound thiolate on the carbon electrophile. Intramolecular hydrogen bonding of an amide NH to the thiolate sulfur reduces the nucleophilicity and consequently, the rate of alkylation more than 30-fold at 25 degrees C. The H-bonding shows an inverse HD isotope effect of 0.33 (60 degrees C) ascribed to differential H-bonding for the two isotopomers due to zero point energy differences. These model studies provide quantitative evaluation of H-bonding on reaction rates relevant to zinc thiol-activating proteins.
ISSN	00278424
e-ISSN	10916490
Journal	Proceedings of the National Academy of Sciences of the United States of America
Issue Number	7
Volume Number	100
Language	English
Publisher	National Academy of Sciences
Publisher Date	2003-04-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Chemistry Sulfhydryl Compounds Zinc Alkylation Hydrogen Bonding Kinetics Models, Molecular Research Support, U.S. Gov't, Non-P.H.S. Multidisciplinary
Content Type	Text
Resource Type	Article
Subject	Multidisciplinary

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