Basicity of a stable carbene, 1,3-di-tert-butylimidazol-2-ylidene, in THF

The basicity of 1,3-di-tert-butylimidazol-2-ylidene (1) was measured in THF against three hydrocarbon indicators. Both ion pairs and free ions were found and the corresponding equilibrium constants were measured. Homoconjugation was not found in either THF or DMSO. The carbene is effectively more ba...

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Veröffentlicht in:Journal of the American Chemical Society 2002-05, Vol.124 (20), p.5757-5761
Hauptverfasser: KIM, Yeong-Joon, STREITWIESER, Andrew
Format: Artikel
Sprache:eng
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Zusammenfassung:The basicity of 1,3-di-tert-butylimidazol-2-ylidene (1) was measured in THF against three hydrocarbon indicators. Both ion pairs and free ions were found and the corresponding equilibrium constants were measured. Homoconjugation was not found in either THF or DMSO. The carbene is effectively more basic in DMSO by several pK units, probably because of hydrogen bonding of 1-H(+) to DMSO. Model ab initio computations are consistent with these results.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja025628j