Absolute configuration of chirally deuterated neopentane

J. Haesler (), I. Schindelholz, E. Riguet, C. G. Bochet and W. Hug ()
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J. Haesler: University of Fribourg, ch. du Musée 9, CH-1700 Fribourg, Switzerland
I. Schindelholz: University of Fribourg, ch. du Musée 9, CH-1700 Fribourg, Switzerland
E. Riguet: University of Fribourg, ch. du Musée 9, CH-1700 Fribourg, Switzerland
C. G. Bochet: University of Fribourg, ch. du Musée 9, CH-1700 Fribourg, Switzerland
W. Hug: University of Fribourg, ch. du Musée 9, CH-1700 Fribourg, Switzerland

Nature, 2007, vol. 446, issue 7135, 526-529

Abstract: Reflections on neopentane A molecule is 'chiral' when it cannot be superimposed on its mirror image; this property is of decisive importance throughout nature, as DNA, proteins, and many small molecules are chiral. Anomalous X-ray scattering has become the definitive method for determining the absolute configuration of a molecule, but this approach cannot be used unless the molecule contains a 'heavy' atom (for example, bromine). Haesler et al. now show that instrumental advances in Raman optical activity, combined with quantum chemical computations, have made it possible to determine the absolute configuration of molecules that do not contain a heavy atom — in this case, a specially synthesized chirally deuterated version of neopentane that represents the archetype of all molecules that are chiral as a result of a dissymmetric mass distribution. The unequivocal spectroscopic determination of the absolute configuration of this molecule presented a major challenge, one that was at the very limit of what is possible.

Date: 2007
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DOI: 10.1038/nature05653

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