title: Neighboring group stabilization by sigma-holes.
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.
authors.affiliation: School of Chemistry and ARC Centre for Free Radical Chemistry and Biotechnology, University of Melbourne, Melbourne, Victoria, 3010, Australia.
authors.forename: Richard A J
authors.initials: RA
authors.lastname: O'Hair
authors.forename: Craig M
authors.initials: CM
authors.lastname: Williams
authors.forename: Timothy
authors.initials: T
authors.lastname: Clark
mesh_terms: D000838:Anions; D001151:Arsenic / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D008958:Models, Molecular; D010758:Phosphorus / Q000737:chemistry*; D011522:Protons; D055672:Static Electricity; D013816:Thermodynamics
chemical_list: D000838:Anions; D007462:Iodobenzenes; D007463:Iodobenzoates; D011522:Protons; D010758:Phosphorus; C476101:o-iodoxybenzoic acid; D007455:Iodine; D001151:Arsenic
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