Twisted push-pull ethylenes

Naduvile Veedu, Rakesh, Bernhardt, Paul V., Koch, Rainer and Wentrup, Curt (2008) Twisted push-pull ethylenes. Australian Journal of Chemistry, 61 10: 805-812. doi:10.1071/CH08277


Author Naduvile Veedu, Rakesh
Bernhardt, Paul V.
Koch, Rainer
Wentrup, Curt
Title Twisted push-pull ethylenes
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 0004-9425
Publication date 2008
Sub-type Article (original research)
DOI 10.1071/CH08277
Volume 61
Issue 10
Start page 805
End page 812
Total pages 8
Place of publication Collingwood, VIC, Australia
Publisher CSIRO Publishing
Collection year 2009
Language eng
Subject C1
030505 Physical Organic Chemistry
970103 Expanding Knowledge in the Chemical Sciences
Abstract 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).
Keyword Molecular-orbital methods
Polarizable Continuum Model
Gaussian basis sets
X-ray-diffraction
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2009 Higher Education Research Data Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 27 Mar 2009, 15:47:01 EST by Jennifer Falknau on behalf of School of Chemistry & Molecular Biosciences