Synthesis and Structural Characterization of 1-Mesityl-1,3-dihydro-imidazole-2-selone and Bis(1-mesitylimidazol-2-yl)diselenide:  Experimental Evidence That the Selone Is More Stable Than the Selenol Tautomer

• Published in: Journal of the American Chemical Society 2006-09, Vol.128 (38), p.12490-12497
• Main Authors: Landry, Victoria K, Minoura, Mao, Pang, Keliang, Buccella, Daniela, Kelly, Bryte V, Parkin, Gerard
• Format: Article
• Language: English
• Subjects: Chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Preparations and properties
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja063168e

1-Mesityl-1,3-dihydro-imidazole-2-selone, (seimMes)H, may be obtained from 1-mesitylimidazole via (i) deprotonation with BunLi, (ii) treatment with elemental selenium, and (iii) addition of HCl(aq). Structural characterization of (seimMes)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 (seimMes)H are oxidized by air to give bis(1-mesitylimidazol-2-yl)diselenide, (seimMes)2. A corresponding investigation of (seimMe)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 77Se NMR studies demonstrate that the (seimR) groups of the selone (seimR)H and diselenide (seimR)2 undergo facile exchange on the NMR time scale.