Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 124, Issue 20, Pages 5757-5761Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja025628j
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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.
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