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Self-Assembly of Gamma-Modified Peptide Nucleic Acids into Complex Nanostructures in Organic Solvent Mixtures

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Published on: June 26, 2020

Neighboring group stabilization by sigma-holes.

Richard A J O'Hair¹, Craig M Williams, Timothy Clark

¹School of Chemistry and ARC Centre for Free Radical Chemistry and Biotechnology, University of Melbourne, Melbourne, Victoria, 3010, Australia.

Journal of Molecular Modeling

|August 18, 2009

Summary

Density-functional theory reveals neighboring-group stabilization in iodine, arsenic, and phosphorus oxyanions. This study analyzes stabilizing effects in compounds like deprotonated 2-iodoxybenzoic acid (IBX).

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Area of Science:

Computational Chemistry
Quantum Chemistry
Materials Science

Background:

Neighboring-group participation is crucial for understanding chemical reactivity and stability.
Oxyanions of iodine, arsenic, and phosphorus exhibit unique electronic properties.
Deprotonated 2-iodoxybenzoic acid (IBX) serves as a model system for studying these phenomena.

Purpose of the Study:

To investigate the neighboring-group stabilization effects in iodine, arsenic, and phosphorus-centered oxyanions.
To analyze the magnitudes of various stabilizing interactions.
To identify potential new systems exhibiting analogous stabilization.

Main Methods:

Application of density-functional theory (DFT) calculations.
Analysis of electronic structure and bonding in selected oxyanion species.
Computational modeling of deprotonated 2-iodoxybenzoic acid (IBX) and its analogs.

Main Results:

Quantification of neighboring-group stabilization in iodine, arsenic, and phosphorus oxyanions.
Detailed analysis of the electronic and steric factors contributing to stabilization.
Identification of specific stabilizing interactions within the studied moieties.

Conclusions:

Neighboring-group effects significantly stabilize iodine, arsenic, and phosphorus oxyanions.
The findings provide insights into the chemical behavior of these important functional groups.
Potential for designing new molecules with enhanced stability based on these principles.