The consequences of freezing the orientation of the oxygen's lone pair orbitals--which determines whether the anomeric effect is operative or not--were studied theoretically and experimentally in two oxobicyclo-[3.1.0]hexane nucleosides (1 and 2). The results showed significant differences in the properties of these molecules, which correlated with the magnitude of the n2 --> sigma * delocalization.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2700545 | PMC |
| http://dx.doi.org/10.1093/nass/nrn275 | DOI Listing |
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