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A halogen bond is almost collinear with the halogen atom's other, conventional bond, but the geometry of the electron-charge donor may be much more complex.. Multi-electron donors such as ethers and amines prefer halogen bonds collinear with the lone pair and donor nucleus.
Halogen bonding is a type of non-covalent interaction which does not involve the formation nor breaking of actual bonds, but rather is similar to the dipole–dipole interaction known as hydrogen bonding. In halogen bonding, a halogen atom acts as an electrophile, or electron-seeking species, and forms a weak electrostatic interaction with a ...
As a halogen source for transhalogenation, metal halides (such as sodium fluoride or lithium fluoride) are often used, but also the use of onium halides is possible. [2] Transhalogenation has been described as a gentle method for the synthesis of fluoroorganylboranes. [ 4 ]
Phenylic hydrogens have extremely strong bonds and are rarely displaced by halogens. Non-enolizable aldehydes oxidize to the acyl halide, but enolizable aldehydes typically halogenate at the α position instead. Indeed, allylic and benzylic hydrogens have bonds much weaker than alkanes, and are selectively replaced in the Wohl-Ziegler reaction.
This regioselectivity is rationalized by the resonance stabilization of a neighboring carbocation by a lone pair on the initially installed halogen. Depending on relative rates of the two steps, it may be difficult to stop at the first stage, and often, mixtures of the mono and bis hydrohalogenation products are obtained.
The rate of dehalogenation depends on the strength of the bond between the carbon and halogen atom. The bond dissociation energies of carbon-halogen bonds are described as: H 3 C−I (234 kJ/mol), H 3 C−Br (293 kJ/mol), H 3 C−Cl (351 kJ/mol), and H 3 C−F (452 kJ/mol). Thus, for the same structures the bond dissociation rate for ...
The bonding in polyhalogen ions mostly invoke the predominant use of p-orbitals. Significant d-orbital participation in the bonding is improbable as much promotional energy will be required, while scant s-orbital participation is expected in iodine-containing species due to the inert-pair effect, suggested by data from Mössbauer spectroscopy ...
Iodine oxides are the most stable of all the halogen oxides, because of the strong I–O bonds resulting from the large electronegativity difference between iodine and oxygen, and they have been known for the longest time. [11] The stable, white, hygroscopic iodine pentoxide (I 2 O 5) has been known since its formation in 1813 by Gay-Lussac and ...