Stereoelectronic Effects

The Anomeric Effect - Methoxy


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By looking at the molecular orbitals of this molecule and the chlorine substituted tetrahydropyran, it is clear that the anomeric effect in this molecule is not as strong in comparison.
In this example the molecular orbitals in the axial and equatorial anomers showing the lone pair donation into the sigma anti-bonding orbital are very similar.


Substituted Tetrahydropyran

Comparison of the anomeric effect in substituted tetrahydropyrans