The basicity of 1,3-di-tert-butylimidazol-2-ylidene (1) was measured in THF against threehydrocarbon indicators. Both ion pairs and free ions were found and the corresponding equilibrium constantswere measured. Homoconjugation was not found in either THF or DMSO. The carbene is effectively morebasic in DMSO by several pK units, probably because of hydrogen bonding of 1-H+ to DMSO. Model abinitio computations are consistent with these results.