On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition-Metal Complexes

Rate versus selectivity determining: The measurement of a kinetic isotope effect (KIE) can provide valuable information about the mechanism of a reaction, but care must be taken in the design and interpretation of KIE experiments. Depending on the experiment that is conducted, the observation of a p...

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Published inAngewandte Chemie International Edition Vol. 51; no. 13; pp. 3066 - 3072
Main Authors Simmons, Eric M., Hartwig, John F.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 26.03.2012
WILEY‐VCH Verlag
Subjects
Bonding
Carbon - chemistry
Cleavage
Coordination Complexes - chemistry
CH functionalization
Deuterium
Deuterium - chemistry
energy diagrams
Hydrogen - chemistry
Isotope effect
isotope effects
Kinetics
rate-determining step
Reaction kinetics
Selectivity
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Summary:Rate versus selectivity determining: The measurement of a kinetic isotope effect (KIE) can provide valuable information about the mechanism of a reaction, but care must be taken in the design and interpretation of KIE experiments. Depending on the experiment that is conducted, the observation of a primary KIE resulting from H/D substitution does not necessarily imply that CH bond cleavage occurs during the rate‐determining step of a reaction. FG=functional group.
Bibliography:ark:/67375/WNG-6FS54NBW-X
NIH - No. GM087901
We thank the NSF (CHE-0910641 to J.F.H.) and NIH (GM087901 to E.M.S.) for funding of this work. We are grateful to Prof. Robert G. Bergman for providing a critical reading of an early draft of this essay, and to two referees for their valuable comments and suggestions.
istex:494B77ED6BFFF473C4D6377EAFA9F9AC438F9A58
NSF - No. CHE-0910641
ArticleID:ANIE201107334
We thank the NSF (CHE‐0910641 to J.F.H.) and NIH (GM087901 to E.M.S.) for funding of this work. We are grateful to Prof. Robert G. Bergman for providing a critical reading of an early draft of this essay, and to two referees for their valuable comments and suggestions.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201107334