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Dramatically Enhanced Solubility of Halide‐Containing Organometallic Species in Diiodomethane: The Role of Solvent⋅⋅⋅Complex Halogen Bonding
Author(s) -
Kinzhalov Mikhail A.,
Kashina Mariya V.,
Mikherdov Alexander S.,
Mozheeva Ekaterina A.,
Novikov Alexander S.,
Smirnov Andrey S.,
Ivanov Daniil M.,
Kryukova Mariya A.,
Ivanov Aleksandr Yu.,
Smirnov Sergej N.,
Kukushkin Vadim Yu.,
Luzyanin Konstantin V.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807642
Subject(s) - diiodomethane , chemistry , solvation , halogen , halogen bond , halide , solubility , solvent , intermolecular force , solvent effects , photochemistry , inorganic chemistry , solvophobic , organic chemistry , polymer chemistry , molecule , alkyl , surface energy
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 CH 2 I 2 were associated with the substantially better σ‐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.