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Review | Regular issue | Vol 32, No. 4, 1991, pp.795-807
Published online, 1st January, 1970
DOI: 10.3987/REV-91-425
The Role of Lone Pair Interactions in the Chemistry of the Monosaccharides. Stereo-electronic Effects in Unsaturated Monosaccharides

Vernon G. S. Box*

*Department of Chemistry, City College of The City University of New York, New York, NY 10031 U.S.A.


The X-ray crystallographic structural data for simple unsaturated monosaccharides do not support the participation of the electron density of a C2-C3 π bond in the modification of the geometry at the anomeric center, or the existence of a vinylogous anomeric effect in glycals. The delocalization phenomena (n-σ*, n-π* and π-σ*) are insignificant in the ground states of the simple sugars, and n-n repulsions are the dominant stereo-electronic effects in these molecules.