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Issue 28, 2012
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Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles

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Abstract

The relative ligand donor strengths of 10 pyrazole-derived ligands has been determined with great accuracy, making use of the interdependence between the donor strength of the co-ligand and the 13C NMR chemical shift of the iPr2-bimy carbene signal in trans-[PdBr2(iPr2-bimy)L] complexes (iPr2-bimy = 1,3-diisopropylbenzimidazolin-2-ylidene; L = pyrazole-derived ligand). Even subtle variations in the substitution pattern of the pyrazole backbone up to three bonds away from the coordinating nitrogen could be detected reliably using this methodology. Alkylation experiments conducted on the pyrazoles using electrophiles of varied reactivity (ethyl bromide, ethyl iodide, and trimethyloxonium tetrafluoroborate) served as a benchmark to rank the pyrazoles in three groups of gradually increasing nucleophilicity, which correlated well with their determined donor strength.

Graphical abstract: Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles

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Supplementary files

Article information


Submitted
05 Mar 2012
Accepted
04 May 2012
First published
04 May 2012

Dalton Trans., 2012,41, 8600-8608
Article type
Paper

Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles

J. C. Bernhammer and H. V. Huynh, Dalton Trans., 2012, 41, 8600
DOI: 10.1039/C2DT30526G

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