Carbonyl Hypoiodites as Extremely Strong Halogen Bond Donors
Yu, S., Ward, J. S., Truong, K.-N., & Rissanen, K. (2021). Carbonyl Hypoiodites as Extremely Strong Halogen Bond Donors. Angewandte Chemie, 60(38), 20739-20743. https://doi.org/10.1002/anie.202108126
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Angewandte ChemieDate
2021Copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH
Neutral halogen-bonded O−I−N complexes were prepared from in situ formed carbonyl hypoiodites and aromatic organic bases. The carbonyl hypoiodites have a strongly polarized iodine atom with larger σ-holes than any known uncharged halogen bond donor. Modulating the Lewis basicity of the selected pyridine derivatives and carboxylates leads to halogen-bonded complexes where the classical O−I⋅⋅⋅N halogen bond transforms more into a halogen-bonded COO−⋅⋅⋅I−N+ ion-pair (salt) with an asymmetric O−I−N moiety. X-ray analyses, NMR studies, and calculations reveal the halogen bonding geometries of the carbonyl hypoiodite-based O−I−N complexes, confirming that in the solid-state the iodine atom is much closer to the N-atom of the pyridine derivatives than its original position at the carboxylate O-atom.
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https://converis.jyu.fi/converis/portal/detail/Publication/99048332
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Academy of FinlandFunding program(s)
Academy Project, AoF
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We are grateful for financial support from the Academy of Finland (K.R.: grant no. 317259), the Finnish Cultural Foundation Central Fund (J.S.W.: grant no. 00201148), the Magnus Ehrnrooth Foundation (J.S.W.), and the University of Jyväskylä.License
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