Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 39, Pages 12785-12789Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807642
Keywords
haloalkanes; halogen bonding; organometallic species; solubility; solvation
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Funding
- Russian Foundation for Basic Research [16-33-60123 mol_a_dk, 18-29-04006, 16-03-00441]
- University of Liverpool
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In the current study, we evaluated the solubility of a number of organometallic species and showed that it is noticeably improved in diiodomethane when compared to other haloalkane solvents. The better solvation properties of CH2I2 were associated with the substantially better sigma-hole-donating ability of this solvent, which results in the formation of uniquely strong solvent-(metal complex) halogen bonding. The strength of the halogen bonding is attenuated by the introduction of additional halogen atoms in the organometallic species owing to the competitive formation of more favourable intermolecular complex-complex halogen bonding. The exceptional solvation properties of diiodomethane and its inertness towards organometallic species make this solvent a good candidate for NMR studies, in particular, for the acquisition of spectra of insensitive spins.
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