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Neighboring group stabilization by σ-holes

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Abstract

We have used density-functional theory to investigate the neighboring-group stabilization of iodine, arsenic, and phosphorus-centered oxyanion moieties in species such as deprotonated 2-iodoxybenzoic acid (IBX) and its analogs. The magnitudes of different stabilizing effects and further candidates for analogous stabilization are analyzed.

The σ-hole colinear with the in-plane I-O bond in PhIO2

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Acknowledgments

This work was supported by the Deutsche Forschungsgemeinschaft as part of SFB583 “Redox-Active Metal Complexes: Control of Reactivity via Molecular Architecture”. The University of Queensland is gratefully acknowledged for financial support.

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Authors and Affiliations

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

    Richard A. J. O’Hair

  2. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia

    Craig M. Williams

  3. Computer-Chemie-Centrum and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nägelsbachstrasse 25, 91052, Erlangen, Germany

    Timothy Clark

Authors
  1. Richard A. J. O’Hair
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  2. Craig M. Williams
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  3. Timothy Clark
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Corresponding author

Correspondence to Timothy Clark.

Electronic supplementary material

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ESM 1

Gaussian archive entries and basis set definition for the calculations mentioned in the text. (DOC 419 kb)

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O’Hair, R.A.J., Williams, C.M. & Clark, T. Neighboring group stabilization by σ-holes. J Mol Model 16, 559–565 (2010). https://doi.org/10.1007/s00894-009-0567-1

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  • DOI: https://doi.org/10.1007/s00894-009-0567-1

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