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    STUDIA CHEMIA - Issue no. 4 / 2014  
         
  Article:   A TWIST IN THE ANOMERIC EFFECT.

Authors:  RADU SILAGHI-DUMITRESCU. 		 
       
         
  Abstract:  Several explanations have been proposed for the anomeric effect – based mainly on sterical interactions, charge separation, and hyperconjugation. Revisiting this topic with computational methods, we find that the pyranoid oxygen is not sp3-hybridized, and as a result of this situation one of the oxygen lone pairs is found in an eclipsed conformation with respect to an equatorial substituent at a neighboring carbon atom. This sterical conflict by itself appears as an important cause of the anomeric effect. The non-sp3-hybridized nature of the oxygen atom is in fact found not to be limited to carbohydrates, but rather be encountered in basic structural motifs (e.g., water, methanol, formaldehyde). Differences between this situation and those encountered with other heteroatoms (nitrogen, sulfur) are also discussed.

Keywords: Anomeric effect; sugar, pyranoid oxygen.
 
         
     
         
         
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