期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 19, 页码 8633-8640出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b13309
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资金
- European Research Council under the European Union's Horizon 2020 research and innovation programme [638337]
- Deutsche Forschungsgemeinschaft (German Research Foundation) under Germany's Excellence Strategy [EXC 2033-390677874-RESOLV]
- European Research Council (ERC) [638337] Funding Source: European Research Council (ERC)
Hypervalent iodine(III) derivatives have been established as powerful reagents in organic transformations, but so far only a handful of studies have addressed their potential use as halogen-bonding noncovalent Lewis acids. In contrast to classical halogen-bond donors based on iodine(I) compounds, iodine(III) salts feature two directional electrophilic axes perpendicular to each other. Herein we present the first systematic investigation on biaxial binding to such Lewis acids in solution. To this end, hindered and unhindered iodolium species were titrated with various substrates, including diesters and diamides, via H-1-NMR spectroscopy and isothermal titration calorimetry. Clear evidence for biaxial binding was obtained in two model systems, and the association strengths increased by 2 orders of magnitude. These findings were corroborated by density functional theory calculations (which reproduced the trend well but underestimated the absolute binding constants) and a cocrystal featuring biaxial coordination of a diamide to the unhindered iodolium compound.
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