Silicon anomeric effects

This illustrates the great affinity of silicon for binding to oxygen donors. Organic chemists usually explain the anomeric effect by double-bond-no-bond... 

In conclusion, the anomeric effect at silicon, although smaller than for carbon, is significant especially for oxygen and it probably plays an important role in determining the preferred conformations of relevant silicon compounds such as disilaoxiranes. 

It would be very interesting to obtain AEl and AEd values for, for example, O—C—O, S—C—S, and Se—C—Se anomeric interactions as a function of appropriate torsion angles so as to establish the relative importance of stabilizing and destabilizing interactions as a source of the observed anomeric effects. So far, NBO analysis has been applied to the elucidation of anomeric effects involving silicon centers (145) (see ref. 144 for a PMO approach), to Se—C—Se anomeric interactions (148), and to the study of fluorinated amines (146) F AH NH2. The amine study showed that due to the two... 

Graczyk PP, Mikolajczyk M (1993) Anomeric effect origin and consequences. Phosphorus Sulfur Silicon Relat Elem 78 313-316... 

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