Assessing the potential of zwitterionic NHOCS2 adducts for probing the stereoelectronic parameters of N-heterocyclic carbenes

Lionel Delaude, Albert Demonceau, Johan Wouters

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Résumé

Five imidazol(in)ium-2-dithiocarboxylates bearing cyclo-hexyl, mesityl, or 2,6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding N-heterocyclic carbenes (NHCs) by reaction with carbon disul-fide. They were characterized by IR, UV/Vis, and NMR spec- troscopy, 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 NHOCS2 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 NHOCO2 adducts were deemed more appropriate for evaluating the a-donating properties of carbene ligands.

langue originaleAnglais
Pages (de - à)1882-1891
Nombre de pages10
journalEuropean Journal of Inorganic Chemistry
Numéro de publication13 SPEC. ISS.
Les DOIs
Etat de la publicationPublié - 1 mai 2009

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  • Ensembles de données

    CCDC 645146: Experimental Crystal Structure Determination

    Delaude, L. (Contributeur), Demonceau, A. (Contributeur) & WOUTERS, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2009

    Ensemble de données

    CCDC 645145: Experimental Crystal Structure Determination

    Delaude, L. (Contributeur), Demonceau, A. (Contributeur) & WOUTERS, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2009

    Ensemble de données

    CCDC 645148: Experimental Crystal Structure Determination

    Delaude, L. (Contributeur), Demonceau, A. (Contributeur) & WOUTERS, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2009

    Ensemble de données

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