A1 Journal article (refereed)
Fluoro and Trifluoromethyl Benzoyl Hypoiodite Complexes with Substituted Pyridines (2024)

Kolařík, V., Rissanen, K., & Ward, J. S. (2024). Fluoro and Trifluoromethyl Benzoyl Hypoiodite Complexes with Substituted Pyridines. Chemistry : An Asian Journal, Early online. https://doi.org/10.1002/asia.202400349

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Publication details

All authors or editors: Kolařík, Václav; Rissanen, Kari; Ward, Jas S.

Journal or series: Chemistry : An Asian Journal

ISSN: 1861-4728

eISSN: 1861-471X

Publication year: 2024

Publication date: 05/04/2024

Volume: Early online

Publisher: Wiley-VCH Verlag

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/asia.202400349

Publication open access: Openly available

Publication channel open access: Partially open access channel

Abstract

Based on the prior observation of the trifluoroacetate hypoiodite, CF3C(O)OI, demonstrating the largest σ-hole of a neutral halogen bond donor, a series of mono- and bis-carbonyl hypoiodites utilising trifluoromethyl or fluorine substituents at various positions of a parent benzoyl skeleton have been synthesised. The carbonyl hypoiodite complexes were prepared via cation exchange of the silver(I) cations with iodine(I) from the respective silver(I) carboxylates and dicarboxylates as the synthetic precursors. A range of pyridinic Lewis bases of varying nucleophilicities were used to stabilise the carbonyl hypoiodites to further probe their properties. The silver(I) intermediates with these Lewis bases were also isolated for silver(I) pentafluorobenzoate, providing additional insight into the cation exchange reaction. All complexes were characterised both in solution (1H, 1H-15N HMBC, 19F) and in the solid state (SCXRD), permitting insights into the formation of the elusive pyridine-iodine(I) cation.

Keywords: coordination complexes; halogens; chemical bonds; chemical synthesis

Free keywords: halogen bonding; hypoiodite; iodine(I); silver; X-ray diffraction

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Preliminary JUFO rating: 1