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.
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...
| Publicado en: | Journal of the American Chemical Society Vol. 128; no. 38; pp. 12490 - 12498 |
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| Autores principales: | , , , , , |
| Formato: | Artículo |
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American Chemical Society
9/27/2006
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=22696500&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 22696500 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 9/27/2006 vid: 128 iid: 38 pid: 997 pub: American Chemical Society artinfo: ui: 22696500 10.1021/ja063168e ppf: 12490 ppct: 8 formats: tig: atl: 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. aug: au: Landry, Victoria K. Minoura, Mao Keliang Pang Buccella, Daniela Kelly, Bryte V. Parkin, Gerard affil: Department of Chemistry, Columbia University, New York, New York 10027 su: Native element minerals Nonmetals Selenium Imidazoles Optical diffraction Chemistry sug: subj: Native element minerals Nonmetals Selenium Imidazoles Optical diffraction Chemistry ab: 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. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2006 holdings: @attributes: islocal: N |
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