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Hyperconjugative and Electrostatic Interactions as Anomeric Triggers in Archetypical 1,4-Dioxane Derivatives

Pilar Gema Rodríguez Ortega1, Manuel Montejo2, Juan Jesús López González2

  • 1Department of Physical and Analytical Chemistry, University of Jaén, 23071, Jaén, Spain. mrortega@ujaen.es.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|December 15, 2015
PubMed
Summary

The anomeric effect in six-membered heterocycles is explained by combined hyperconjugation and electrostatic factors, not a single cause. Polar solvents favor the beta-anomer by reducing electrostatic repulsion.

Keywords:
anomeric effectdensity functional calculationsnatural bond orbitalsvibrational spectroscopyα/β ratios

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