Computational evidence that hyperconjugative interactions are not responsible for the anomeric effect
- 4 July 2010
- journal article
- Published by Springer Nature in Nature Chemistry
- Vol. 2 (8) , 666-671
- https://doi.org/10.1038/nchem.721
Abstract
The anomeric effect, which influences the position of polar substituents in the chair conformation of various heterocycles, is commonly rationalized using hyperconjugation. Now, by theoretically studying molecules that display the anomeric effect, strong evidence is provided that hyperconjugation is not responsible and it is better interpreted in terms of electrostatics.Keywords
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