Assessing the Potential of Zwitterionic NHC•CS2 Adducts for Probing the Stereoelectronic Parameters of N-Heterocyclic Carbenes

Delaude, Lionel; Demonceau, Albert; Wouters, Johan

doi:10.1002/ejic.200801110

Article (Scientific journals)

Assessing the Potential of Zwitterionic NHC•CS2 Adducts for Probing the Stereoelectronic Parameters of N-Heterocyclic Carbenes

Delaude, Lionel; Demonceau, Albert; Wouters, Johan

2009 • In European Journal of Inorganic Chemistry, (13), p. 1882-1891

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https://hdl.handle.net/2268/15436

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10.1002/ejic.200801110

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Keywords :

Betaines; Carbenes; Ligand effects; Nitrogen heterocycles; Zwitterions

Abstract :

[en] Five imidazol(in)ium-2-dithiocarboxylates bearing cyclohexyl, mesityl, or 2,6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding N-heterocyclic carbenes (NHCs) by reaction with carbon disulfide. They were characterized by IR, UV/Vis, and NMR spectroscopy, and by thermogravimetric analysis. Their molecular structures were determined by X-ray diffraction. For the sake of comparison, tricyclohexylphosphonium dithiocarboxylate was also examined. The data acquired were scrutinized to evaluate their usefulness for assessing the steric and electronic properties of NHC ligands. Because of their outstanding ability to crystallize, the five NHC center dot CS2 betaines were found to be highly suitable for probing the steric influence of nitrogen atom substituents on imidazolylidene-based ligand precursors via XRD analysis, while the corresponding NHC center dot CO2 adducts were deemed more appropriate for evaluating the sigma-donating properties of carbene ligands. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Disciplines :

Chemistry

Author, co-author :

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Wouters, Johan

Language :

English

Title :

Assessing the Potential of Zwitterionic NHC•CS2 Adducts for Probing the Stereoelectronic Parameters of N-Heterocyclic Carbenes

Publication date :

2009

Journal title :

European Journal of Inorganic Chemistry

ISSN :

1434-1948

eISSN :

1099-0682

Publisher :

Wiley-VCH Verlag Gmbh, Weinheim, Germany

Issue :

Pages :

1882-1891

Peer reviewed :

Peer Reviewed verified by ORBi

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since 26 June 2009

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