{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T06:45:45Z","timestamp":1791096345660,"version":"4.1.0"},"reference-count":59,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2009,6,3]],"date-time":"2009-06-03T00:00:00Z","timestamp":1243987200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2010,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>N\u2010alkylated <jats:italic>trans<\/jats:italic>\u2010diaziridines are an intriguing class of compounds with two stereogenic nitrogen atoms which easily interconvert. In the course of our investigations of the nature of the interconversion process via nitrogen inversion or electrocyclic ring opening ring closure, we synthesized and characterized the three constitutionally isomeric diaziridines 1,2\u2010di\u2010<jats:italic>n<\/jats:italic>\u2010propyldiaziridine <jats:bold>1<\/jats:bold>, 1\u2010isopropyl\u20102\u2010<jats:italic>n<\/jats:italic>\u2010propyldiaziridine <jats:bold>2<\/jats:bold>, and 1,2\u2010diisopropyldiaziridine <jats:bold>3<\/jats:bold> to study the influence of the substituents on the interconversion barriers. Enantiomer separation was achieved by enantioselective gas chromatography on the chiral stationary phase Chirasil\u2010\u03b2\u2010Dex with high separation factors \u03b1 (1\u2010isopropyl\u20102\u2010<jats:italic>n<\/jats:italic>\u2010propyldiaziridine: 1.18; 1, 2\u2010diisopropyldiaziridine: 1.24; 100\u00b0C 50 kPa He) for the isopropyl substituted diaziridines. These compounds showed pronounced plateau formation between 100 and 150\u00b0C, and peak coalescence at elevated temperatures. The enantiomerization barriers \u0394<jats:italic>G<\/jats:italic>\u2021 and activation parameters \u0394<jats:italic>H<\/jats:italic>\u2021 and \u0394<jats:italic>S<\/jats:italic>\u2021 were determined by enantioselective dynamic gas chromatography (DGC) and direct evaluation of the elution profiles using the unified equation implemented in the software DCXplorer. Interestingly, 1\u2010isopropyl\u20102\u2010<jats:italic>n<\/jats:italic>\u2010propyldiaziridine and 1,2\u2010diisopropyldiaziridine exhibit similar high interconversion barriers \u0394<jats:italic>G<\/jats:italic>\u2021 (100\u00b0C) of 128.3 \u00b1 0.4 kJ mol<jats:sup>\u22121<\/jats:sup> and 129.8 \u00b1 0.4 kJ mol<jats:sup>\u22121<\/jats:sup>, respectively, which indicates that two sterically demanding substituents do not substantially increase the barrier as expected for a distinct nitrogen inversion process. Chirality, 2010. \u00a9 2009 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20742","type":"journal-article","created":{"date-parts":[[2009,6,3]],"date-time":"2009-06-03T20:43:56Z","timestamp":1244061836000},"page":"284-291","source":"Crossref","is-referenced-by-count":22,"title":["The stereodynamics of 1,2\u2010dipropyldiaziridines"],"prefix":"10.1002","volume":"22","author":[{"given":"Oliver","family":"Trapp","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laila","family":"Sahraoui","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Werner","family":"Hofstadt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Werner","family":"K\u00f6nen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,6,3]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300595"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac060194m"},{"key":"e_1_2_1_4_2","first-page":"147","article-title":"The racemization of enantiopure drugs: helping medicinal chemists to approach the problem","volume":"2","author":"Reist M","year":"1997","journal-title":"Enantiomer"},{"key":"e_1_2_1_5_2","unstructured":"WernerA.\u00dcber die r\u00e4umliche anordnung der atome in stickstoffhaltigen molek\u00fclen Doctoral Thesis. 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