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Reaction of <jats:bold>1<\/jats:bold>\u2013<jats:bold>4<\/jats:bold> with diiodine in a 1:1 molar ratio in dichloromethane results in the formation of [(RSeU)I<jats:sub>2<\/jats:sub>] (R = methyl (<jats:bold>5<\/jats:bold>), ethyl (<jats:bold>6<\/jats:bold>), <jats:italic>n<\/jats:italic>\u2010propyl (<jats:bold>7<\/jats:bold>) and isopropyl (<jats:bold>8<\/jats:bold>)). All compounds have been characterized by elemental analysis, FT\u2010Raman, FT\u2010IR, UV\/Vis, <jats:sup>1<\/jats:sup>H\u2013, <jats:sup>13<\/jats:sup>C\u2013, <jats:sup>77<\/jats:sup>Se\u20131D and \u20102D NMR spectroscopy, and ESI\u2010MS spectrometric techniques. Recrystallization of <jats:bold>4<\/jats:bold> from dichloromethane afforded (<jats:bold>4<\/jats:bold>\u22c5CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>). Crystals of [(<jats:italic>n<\/jats:italic>PrSeU)I<jats:sub>2<\/jats:sub>] (<jats:bold>7<\/jats:bold>), a charge\u2010transfer complex, were obtained from chloroform solutions, while crystallization of <jats:bold>6<\/jats:bold> and <jats:bold>7<\/jats:bold> from acetone afforded the diselenides [<jats:italic>N<\/jats:italic>\u2010(6\u2010Et\u20104\u2010pyrimidone)(6\u2010EtSeU)<jats:sub>2<\/jats:sub>] (<jats:bold>9<\/jats:bold>\u22c52\u2009H<jats:sub>2<\/jats:sub>O) and [<jats:italic>N<\/jats:italic>\u2010(6\u2010<jats:italic>n<\/jats:italic>Pr\u20104\u2010pyrimidone)(6\u2010<jats:italic>n<\/jats:italic>PrSeU)<jats:sub>2<\/jats:sub>] (<jats:bold>10<\/jats:bold>) as oxidation products. Recrystallization of <jats:bold>7<\/jats:bold> from methanol\/acetonitrile solutions led to deselenation with the formation of 6\u2010<jats:italic>n<\/jats:italic>\u2010propyl\u20102\u2010uracil (<jats:italic>n<\/jats:italic>PrU) (<jats:bold>11<\/jats:bold>). [(<jats:italic>n<\/jats:italic>PrSeU)I<jats:sub>2<\/jats:sub>] (<jats:bold>7<\/jats:bold>) was found to be a charge\u2010transfer complex with a Se\uf8ffI bond. These results are discussed in relation to the mechanism of action of antithyroid drugs.<\/jats:p>","DOI":"10.1002\/chem.200501455","type":"journal-article","created":{"date-parts":[[2006,6,14]],"date-time":"2006-06-14T04:32:40Z","timestamp":1150259560000},"page":"6888-6897","source":"Crossref","is-referenced-by-count":34,"title":["Synthesis and Structures of Se Analogues of the Antithyroid Drug 6\u2010<i>n<\/i>\u2010Propyl\u20102\u2010thiouracil and Its Alkyl Derivatives: Formation of Dimeric Se\u2013Se Compounds and Deselenation Reactions of Charge\u2010Transfer Adducts of Diiodine"],"prefix":"10.1002","volume":"12","author":[{"given":"Constantinos D.","family":"Antoniadis","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sotiris K.","family":"Hadjikakou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nick","family":"Hadjiliadis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Athanasios","family":"Papakyriakou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Baril","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ian S.","family":"Butler","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,8,29]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/349438a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)98657-6"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010702)113:13<2547::AID-ANGE2547>3.0.CO;2-R"},{"key":"e_1_2_6_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010702)40:13<2486::AID-ANIE2486>3.0.CO;2-N"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","first-page":"189","volume-title":"Biochemistry of Deiodination in Thyroid Hormone Metabolism","author":"Leonard J. 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