NDLI: Structure and Reactivity of the Cysteine Methyl Ester Radical Cation

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Structure and Reactivity of the Cysteine Methyl Ester Radical Cation

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Van Stipdonk, Michael Ryzhov, Victor Steill, Jeffrey D. Osburn, Sandra O'hair, Richard A. J. Oomens, Jos
Description	Author Affiliation: Osburn S ( Department of Chemistry and Biochemistry, Northern Illinois University, Dekalb, USA.)
Abstract	The structure and reactivity of the cysteine methyl ester radical cation, $CysOMe^{.+},$ have been examined in the gas phase using a combination of experiment and density functional theory (DFT) calculations. $CysOMe^{.+}$ undergoes rapid ion–molecule reactions with dimethyl disulfide, allyl bromide, and allyl iodide, but is unreactive towards allyl chloride. These reactions proceed by radical atom or group transfer and are consistent with $CysOMe^{.+}$ possessing structure 1, in which the radical site is located on the sulfur atom and the amino group is protonated. This contrasts with DFT calculations that predict a captodative structure 2, in which the radical site is positioned on the α carbon and the carbonyl group is protonated, and that is more stable than 1 by $13.0 kJ mol^{−1}.$ To resolve this apparent discrepancy the gas-phase IR spectrum of $CysOMe^{.+}$ was experimentally determined and compared with the theoretically predicted IR spectra of a range of isomers. An excellent match was obtained for 1. DFT calculations highlight that although 1 is thermodynamically less stable than 2, it is kinetically stable with respect to rearrangement.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	3
Volume Number	17
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2011-01-17
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Cations Chemistry Cysteine Analogs & Derivatives Computer Simulation Gases Isomerism Kinetics Molecular Structure Spectrophotometry, Infrared Tandem Mass Spectrometry Thermodynamics Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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