Conformational structure and energetics of 2-methylphenyl(2'-methoxyphenyl)iodonium chloride: evidence for solution clusters.

Chemistry : a European Journal
Yong-Sok LeeVictor W Pike

Abstract

Diaryliodonium salts allow the efficient incorporation of cyclotron-produced [(18)F]fluoride ions into electron-rich and electron-deficient arenes to provide potential radiotracers for molecular imaging in vivo with positron emission tomography (PET). This process (ArI(+)Ar'+(18)F(-)→Ar(18)F+Ar'I) is still not well understood mechanistically. To better understand this and similar reactions, it would be valuable to understand the structures of diaryliodonium salts in organic media, where the reactions are typically conducted. In this endeavor, the X-ray structure of a representative iodonium salt, 2-methylphenyl(2'-methoxyphenyl)iodonium chloride (1), was determined. Our X-ray structure analysis showed 1 to have the conformational M-P dimer as the unit cell with hypervalent iodine as a stereogenic center in each conformer. With the ab initio replica path method we constructed the inversion path between the two enantiomers of 1, thereby revealing two additional pairs of enantiomers that are likely to undergo fast interconversion in solution. Also LC-MS of 1 showed the presence of dimeric and tetrameric anion-bridged clusters in weak organic solution. This observation is consistent with the energetics of 1, both as monomeric and d...Continue Reading

References

May 9, 1996·Chemical Reviews·Peter J. Stang, Viktor V. Zhdankin
Jul 11, 2002·Chemical Reviews·Viktor V Zhdankin, Peter J Stang
Jun 1, 2007·Journal of the American Chemical Society·Tobias L RossHeinz H Coenen
Nov 7, 2008·Chemical Reviews·Viktor V Zhdankin, Peter J Stang
Oct 31, 2009·Angewandte Chemie·Eleanor A Merritt, Berit Olofsson

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Citations

Aug 17, 2011·Organic & Biomolecular Chemistry·Sanjay TeluVictor W Pike
Feb 2, 2017·Chemistry : a European Journal·Yong-Sok LeeVictor W Pike
Oct 6, 2017·Journal of Labelled Compounds & Radiopharmaceuticals·Victor W Pike
Oct 23, 2012·Angewandte Chemie·Matthew Tredwell, Véronique Gouverneur
Jun 16, 2016·Chemistry : a European Journal·François GuérardMartin W Brechbiel
Mar 4, 2020·Journal of the American Chemical Society·Robert J MayerClaude Y Legault

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