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- W2129232877 abstract "1-(Tri-O-acetyl-α-D-xylopyranosyl)imidazol (1) liegt im Kristall auch ohne wesentlichen Beitrag eines inversen anomeren Effektes in der 1C4-Konformation 1b mit drei axialen Acetyl- und äquatorialer Imidazolgruppe vor. Sterische Gründe sollten hierfür bestimmend sein. In Lösung liegt der Anteil an 1C4-Konformation 1b zwischen 35 und 85%. Die dreidimensionale Röntgenstrukturanalyse von 1 (Raumgruppe rhombisch P 21212) zeigt, daß infolge 1,3-syn-diaxialer Wechselwirkung der 2-OAc-und-4OAc-Gruppe das C4 des Pyranosesessels von 1b abgeflacht ist. Der Imidazolring steht senkrecht zum Pyranosering und senkrecht auf der abgedrehten 2-OAc-Gruppe. Die Methylgruppe der 2-OAc-Gruppe weist eine, die der 3-OAc- und 4-OAc-Gruppe zwei statistisch verteilte Wasserstofflagen auf. Conformation Analysis, VIII. Tria-axial Conformation of 1-(Tri-O-acetyl-α-D-xylopyranosyl)imidazol in Crystal In the crystalline state 1-(tri-O-acetyl-α-D-xylopyranosyl)imidazole (1) adopts the 1C4 conformation 1b with three axial acetoxy groups and one equatorial imidazol group without considerable contribution of an inverse anomeric effect. This is a consequence of predominating steric effects. In solution the amount of 1C4 conformation 1b varies from 35–85%. The three dimensional X-ray structure analysis of 1 (space group rhombic P 21212) shows that owing to a 1,3-syn-diaxial interaction of the 2-OAc and the 4-OAc groups the pyranose chair of 1b is flattened at C4. The plane of the imidazol ring is perpendicular to the pyranose chair and also perpendicular to the turned 2-OAc group. The methyl group of the 2-OAc group exhibits one, those of the 3-OAc and 4-OAc groups exhibit two statistically distributed hydrogen positions." @default.
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- W2129232877 title "Konformationsanalyse, VIII. Tri‐axiale Konformation des 1‐(Tri‐ <i>O</i> ‐acetyl‐α‐ <scp>D</scp> ‐xylopyranosyl)‐imidazols im Kristall" @default.
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- W2129232877 doi "https://doi.org/10.1002/cber.19741070823" @default.
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