Iodine compounds

Chemical compounds containing iodine
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|+ style="margin bottom: 5px;" | Halogen bond energies (kJ/mol) By the same token, however, since iodine has the lowest ionisation energy among the halogens and is the most easily oxidised of them, it has a more significant cationic chemistry and its higher oxidation states are rather more stable than those of bromine and chlorine, for example in iodine heptafluoride.

The iodine molecule, I2, dissolves in CCl4 and aliphatic hydrocarbons to give bright violet solutions. In these solvents the absorption band maximum occurs in the 520 – 540 nm region and is assigned to a * to σ* transition. When I2 reacts with Lewis bases in these solvents a blue shift in I2 peak is seen and the new peak (230 – 330 nm) arises that is due to the formation of adducts, which are referred to as charge transfer complexes.

Organoiodine compounds have been fundamental in the development of organic synthesis, such as in the Hofmann elimination of amines, the Williamson ether synthesis, the Wurtz coupling reaction, and in Grignard reagents. The carbon–iodine bond is a common functional group that forms part of core organic chemistry; formally, these compounds may be thought of as organic derivatives of the iodide anion. The simplest organoiodine compounds, alkyl iodides, may be synthesised by the reaction of alcohols with phosphorus triiodide; these may then be used in nucleophilic substitution reactions, or for preparing Grignard reagents. The C–I bond is the weakest of all the carbon–halogen bonds due to the minuscule difference in electronegativity between carbon (2.55) and iodine (2.66). As such, iodide is the best leaving group among the halogens, to such an extent that many organoiodine compounds turn yellow when stored over time due to decomposition into elemental iodine; as such, they are commonly used in organic synthesis, because of the easy formation and cleavage of the C–I bond. They are also significantly denser than the other organohalogen compounds thanks to the high atomic weight of iodine. A few organic oxidising agents like the iodanes contain iodine in a higher oxidation state than −1, such as 2 iodoxybenzoic acid, a common reagent for the oxidation of alcohols to aldehydes, and iodobenzene dichloride (PhICl2), used for the selective chlorination of alkenes and alkynes. One of the more well known uses of organoiodine compounds is the so called iodoform test, where iodoform (CHI3) is produced by the exhaustive iodination of a methyl ketone (or another compound capable of being oxidised to a methyl ketone), as follows:

Some drawbacks of using organoiodine compounds as compared to organochlorine or organobromine compounds is the greater expense and toxicity of the iodine derivatives, since iodine is expensive and organoiodine compounds are stronger alkylating agents. For example, iodoacetamide and iodoacetic acid denature proteins by irreversibly alkylating cysteine residues and preventing the reformation of disulfide linkages. Halogen exchange to produce iodoalkanes by the Finkelstein reaction is slightly complicated by the fact that iodide is a better leaving group than chloride or bromide. The difference is nevertheless small enough that the reaction can be driven to completion by exploiting the differential solubility of halide salts, or by using a large excess of the halide salt. The reaction is driven toward products by mass action due to the precipitation of the insoluble salt.