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Twisted push–pull ethylenes

Veedu, R.N., Bernhardt, P.V., Koch, R. and Wentrup, C. (2008) Twisted push–pull ethylenes. Australian Journal of Chemistry, 61 (10). pp. 805-812.

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As determined by X-ray crystallography, Meldrum’s acid derivatives 5, 6, and 8 feature dihedral angles around the central C5=C7 double bond of 14–35°, whereas for the anion 9 this angle is 90°. Density functional theory and MP2 calculations are in agreement with the experimental X-ray data for compounds 5–8, but for anion 9 an angle of only ~65° is predicted. It is concluded that a part of the torsion is due to packing forces in the crystal. It is further concluded that these molecules undergo rapid rotation about the central CC bonds at room temperature (calculated activation barriers 5–14 kcal mol–1).

Item Type: Journal Article
Publisher: Commonwealth Scientific and Industrial Research Organization Publishing
Copyright: © 2008 CSIRO
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