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Tartaronitriles – the Derivatives of Tartaric Acid with a Bent Conformation

Gawroński J., Gawrońska K., Waścinska N., Plutecka A., Rychlewska U.

Polish Journal of Chemistry

2007

Vol. 81, nr 11

1917-1925

Conformational preferences of dinitrile derivatives of (R,R)-tartaric acid were studied by means of NMR, CD and X-ray diffraction techniques. Where as other derivatives of (R,R)-tartaric acid exist predom i nantly in an extended (T) or bent (G–) conformation, (R,R)-tartarodinitriles show pronounced tendency to ward bent G+ conformation. This is rationalized by the presence of the “gauche effect” in volving maximum number of stabilizing in teractions between the polar groups within the tartarodinitrile molecule.