Anomeric effect

{
  "id": "MLC-T-CHM-000637",
  "term": "Anomeric effect",
  "field": "Chemistry",
  "definition": "The stereoelectronic preference for an electronegative substituent at the anomeric carbon of a pyranose or furanose ring to adopt an axial orientation. This effect stabilizes the axial conformer over the equatorial one, contrary to steric expectations. It is particularly pronounced in carbohydrate chemistry and related heterocyclic systems.",
  "subject": "Organic and Biomolecular Chemistry",
  "see_also": [
    "axial",
    "conformation",
    "endo, exo, syn, anti",
    "gauche",
    "torsion angle"
  ],
  "references": [
    "PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2198 (https://doi.org/10.1351/pac199668122193)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/anomeric-effect/"
}