{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T23:01:26Z","timestamp":1791414086484,"version":"4.3.3"},"reference-count":9,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2003,2,10]],"date-time":"2003-02-10T00:00:00Z","timestamp":1044835200000},"content-version":"vor","delay-in-days":40,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2003,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The thermally interconvertible diastereomers of the (5S)\u2010methyl\u20103\u2010(<jats:italic>o<\/jats:italic>\u2010aryl)\u20102,4\u2010oxazolidinediones were synthesized and their conformers studied by <jats:sup>1<\/jats:sup>H NMR and HPLC. The barriers to rotation about the N\u2010C<jats:sub>aryl<\/jats:sub> bond were found to be very much solvent dependent. For the <jats:italic>o<\/jats:italic>\u2010fluoro oxazolidinedione, difference in barriers to rotation in deuterated methanol and deuterated chloroform amounted to 34 kJ\/mol. <jats:italic>ortho<\/jats:italic>\u2010Bromo substitution increased the barrier to rotation up to 100 kJ\/mol in ethanol, which enabled the analytical separation of the diastereomers and observation of the thermodynamic enrichment of the <jats:bold>S\u2010P<\/jats:bold> conformer by HPLC. In CDCl<jats:sub>3<\/jats:sub> by <jats:sup>1<\/jats:sup>H NMR, on the other hand, a barrier of only 89 kJ\/mol was determined. The <jats:bold>S\u2010M<\/jats:bold> and <jats:bold>S\u2010P<\/jats:bold> conformers of the diastereomers of <jats:italic>o<\/jats:italic>\u2010methyl, \u03b1\u2010naphthyl and <jats:italic>o<\/jats:italic>\u2010iodo derivatives have been assigned by NOESY experiments and the kinetic and thermodynamic constants for the interconversion between the <jats:bold>S\u2010M<\/jats:bold> and <jats:bold>S\u2010P<\/jats:bold> conformers were determined. Chirality 15:242\u2013250, 2003. \u00a9 2003 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.10189","type":"journal-article","created":{"date-parts":[[2003,2,11]],"date-time":"2003-02-11T23:36:42Z","timestamp":1045006602000},"page":"242-250","source":"Crossref","is-referenced-by-count":21,"title":["Conformational preferences in diastereomeric(5S)\u2010methyl\u20103\u2010(<i>o<\/i>\u2010aryl)\u20102,4\u2010oxazolidinediones"],"prefix":"10.1002","volume":"15","author":[{"given":"\u00d6znur","family":"Demir","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0130lknur","family":"Do\u011fan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2003,2,10]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"crossref","first-page":"1557","DOI":"10.1039\/p29930001557","article-title":"The enantiomers of N\u2010aryl\u20102\u2010thioxo\u20104\u2010oxazolidinones and N\u2010arylrhodanines. Investigation by liquid chromatography, circular dichroism and thermal racemization","author":"Do\u011fan \u0130","year":"1993","journal-title":"J Chem Soc Perkin Trans 2"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)88256-9"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01533a042"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1270120311"},{"key":"e_1_2_1_6_2","first-page":"337","volume-title":"Organic reactions","author":"Smith PAS","year":"1946"},{"key":"e_1_2_1_7_2","volume-title":"Nuclear magnetic resonance spectroscopy","author":"Sohar P","year":"1984"},{"key":"e_1_2_1_8_2","volume-title":"Physical chemistry","author":"Alberty RA","year":"1992"},{"key":"e_1_2_1_9_2","volume-title":"Stereochemistry of organic compounds","author":"Eliel EL","year":"1994"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570330412"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.10189","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.10189","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,6]],"date-time":"2023-10-06T20:01:13Z","timestamp":1696622473000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.10189"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2003,1]]},"references-count":9,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2003,1]]}},"alternative-id":["10.1002\/chir.10189"],"URL":"https:\/\/doi.org\/10.1002\/chir.10189","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2003,1]]}}}