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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546

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Volume 85, Issue 10


The structure of halonium ions in superacidic solutions

Brian K. Ohta
Published Online: 2013-09-12 | DOI: https://doi.org/10.1351/pac-con-13-04-06

Isotopic perturbation of equilibrium was applied to 1,2-bridged halonium ions to determine whether they exist as single symmetric structures or as a rapid equilibrium of asymmetric structures. The observed deuterium isotope shifts are qualitatively and quantitatively consistent with the presence of intrinsic and equilibrium isotope shifts. The presence of equilibrium shifts suggests that these ions exist as a rapid equilibrium of asymmetric structures. Though the asymmetric structures were initially ascribed to β-halocarbenium ions, subsequent computational data suggest that 1,2-bridged halonium ions react with sulfur dioxide (SO2), the experimental solvent. Our current hypothesis is that the equilibrium isotope shifts result from rapid labile addition of SO2 to the halonium ions. Other hypotheses have been invoked to explain the results and are considered in the context of the available data.

: carbocations; chemical equilibrium; isotopes; NMR; reaction mechanisms


, 2012-09-09 - 2012-09-13, International Conference on Physical Organic Chemistry (ICPOC-21), 21st, Durham, UK

About the article

Published Online: 2013-09-12

Published in Print: 2013-10-01

Citation Information: Pure and Applied Chemistry, Volume 85, Issue 10, Pages 1959–1965, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac-con-13-04-06.

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