| Sumario: | 1-Mesityl-1,3-dihydro-imidazole-2-selone, (seim)H, may be obtained from 1-mesitylimidazole via (i) deprotonation with BuLi, (ii) treatment with elemental selenium, and (iii) addition of HCl(aq). Structural characterization of (seim)H by X-ray diffraction demonstrates that the compound exists as the selone rather than selenol tautomer, a result that is in accord with DFT calculations. Solutions of (seim)H are oxidized by air to give bis(1-mesitylimidazol-2-yl)diselenide, (seim). A corresponding investigation of (seim)H demonstrates that, in contrast to a previous report, the selenium analogue of methimazole exists in the selone form with a structure analogous to that of methimazole. ¹H and Se NMR studies demonstrate that the (seim) groups of the selone (seim)H and diselenide (seim) undergo facile exchange on the NMR time scale.
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