Abstract
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.
Original language | English |
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Pages (from-to) | 1882-1891 |
Number of pages | 10 |
Journal | European Journal of Inorganic Chemistry |
Issue number | 13 SPEC. ISS. |
DOIs | |
Publication status | Published - 1 May 2009 |
Keywords
- Betaines
- Carbenes
- Ligand effects
- Nitrogen heterocycles
- Zwitterions
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CCDC 645147: Experimental Crystal Structure Determination
Delaude, L. (Contributor), Demonceau, A. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccpnb6v, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpnb6v&sid=DataCite
Dataset
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CCDC 645146: Experimental Crystal Structure Determination
Delaude, L. (Contributor), Demonceau, A. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccpnb5t, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpnb5t&sid=DataCite
Dataset
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CCDC 645144: Experimental Crystal Structure Determination
Delaude, L. (Contributor), Demonceau, A. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2009
DOI: 10.5517/ccpnb3r, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpnb3r&sid=DataCite
Dataset