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
2009In European Journal of Inorganic Chemistry, (13), p. 1882-1891
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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 :
13
Pages :
1882-1891
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 26 June 2009

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