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Electronic delocalization contribution to the anomeric effect evaluated by computational methods.

F Cortés1, J Tenorio, O Collera

  • 1Instituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, Coyoacán 04510, México, D.F., México.

The Journal of Organic Chemistry
|April 28, 2001
PubMed
Summary

This study introduces a computational method to quantify the electronic delocalization contribution to the Anomeric Effect (EDCAE). This approach helps differentiate stereoelectronic anomeric effects from other influences on molecular conformation.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Quantum Chemistry

Background:

  • The Anomeric Effect (AE) describes the conformational preference of substituents at the anomeric position in heterocyclic compounds.
  • Existing methods for evaluating AE can be complex, necessitating a more direct computational approach.

Purpose of the Study:

  • To develop and validate a computational method, the electronic delocalization contribution to the Anomeric Effect (EDCAE), for assessing the axial preference in heterocyclic compounds.
  • To distinguish between stereoelectronic and non-stereoelectronic origins of the AE.

Main Methods:

  • Utilized Natural Bond Orbital (NBO) analysis to calculate EDCAE.
  • Compared fully delocalized molecules with hypothetical Lewis molecules (lacking delocalization) while maintaining identical geometry.

Related Experiment Videos

  • Employed B3LYP/6-31G(d,p) and HF/6-31G(d,p)//B3LYP/6-31G(d,p) levels of theory for calculations on cyclic and acyclic systems.

    • Main Results:

    • Identified stereoelectronic origins for the AE of Cl in 1,3-dioxane and F, Cl, SMe, PH(3), CO(2)Me in 1,3-dithiane.
    • Found non-stereoelectronic origins for the preference of F, OMe, NH(2) in 1,3-dioxane and P(O)Me(2) in 1,3-dithiane.
    • Demonstrated that non-stereoelectronic anomeric effects can influence molecular geometry, aligning with the double-bond no-bond model.

    Conclusions:

    • The EDCAE method provides a reliable computational alternative for evaluating the stereoelectronic component of the Anomeric Effect.
    • This methodology successfully differentiates between various substituent preferences at the anomeric position based on their electronic origins.
    • The study confirms the applicability of the EDCAE approach across different molecular systems and theoretical levels.