Halocarbon compounds are chemical compounds in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms (fluorine, chlorine, bromine, iodine, or astatine – group 17) resulting in the formation of organofluorine compounds, organochlorine compounds, organobromine compounds, organoiodine compounds, and organoastatine compounds. Chlorine halocarbons are the most common and are called organochlorides. Many synthetic organic compounds such as plastic polymers, and a few natural ones, contain halogen atoms; they are known as halogenated compounds or organohalogens. Organochlorides are the most common industrially used organohalides, although the other organohalides are used commonly in organic synthesis. Except for extremely rare cases, organohalides are not produced biologically, but many pharmaceuticals are organohalides. Notably, many pharmaceuticals such as Prozac have trifluoromethyl groups. For information on inorganic halide chemistry, see halide.
Chemical families
Halocarbons are typically classified in the same ways as the similarly structured organic compounds that have hydrogen atoms occupying the molecular sites of the halogen atoms in halocarbons. Among the chemical families are:
haloalkanes—compounds with carbon atoms linked by single bonds haloalkenes—compounds with one or more double bonds between carbon atoms haloaromatics—compounds with carbons linked in one or more aromatic rings with a delocalised donut shaped pi cloud. The halogen atoms in halocarbon molecules are often called "substituents," as though those atoms had been substituted for hydrogen atoms. However halocarbons are prepared in many ways that do not involve direct substitution of halogens for hydrogens.
History and context A few halocarbons are produced in massive amounts by microorganisms. For example, several million tons of methyl bromide are estimated to be produced by marine organisms annually. Most of the halocarbons encountered in everyday life – solvents, medicines, plastics – are man-made. The first synthesis of halocarbons was achieved in the early 1800s. Production began accelerating when their useful properties as solvents and anesthetics were discovered. Development of plastics and synthetic elastomers has led to greatly expanded scale of production. A substantial percentage of drugs are halocarbons.
Natural halocarbons A large amount of the naturally occurring halocarbons, such as dioxins, are created by wood fire and volcanic activity. A third major source is marine algae, which produce several chlorinated methane and ethane containing compounds. Several thousand complex halocarbons are known to be produced mainly by marine species. Although chlorine compounds are the majority of the discovered compounds, bromides, iodides and fluorides have also been found in nature. Tyrian purple is a bromide and is produced by certain sea snails. Thyroxine is secreted by the thyroid gland and is an iodide. The highly toxic fluoroacetate is one of the rare natural organofluorides and is produced by certain plants.
Organoiodine compounds, including biological derivatives
Organoiodine compounds, called organic iodides, are similar in structure to organochlorine and organobromine compounds, but the C-I bond is weaker. Many organic iodides are known, but few are of major industrial importance. Iodide compounds are mainly produced as nutritional supplements. The thyroxin hormones are essential for human health, hence the usefulness of iodized salt. Six mg of iodide a day can be used to treat patients with hyperthyroidism due to its ability to inhibit the organification process in thyroid hormone synthesis, the so-called Wolff–Chaikoff effect. Prior to 1940, iodides were the predominant antithyroid agents. In large doses, iodides inhibit proteolysis of thyroglobulin, which permits TH to be synthesized and stored in colloid, but not released into the bloodstream. This mechanism is referred to as Plummer effect. This treatment is seldom used today as a stand-alone therapy despite the rapid improvement of patients immediately following administration. The major disadvantage of iodide treatment lies in the fact that excessive stores of TH accumulate, slowing the onset of action of thioamides (TH synthesis blockers). In addition, the functionality of iodides fades after the initial treatment period. An "escape from block" is also a concern, as extra stored TH may spike following discontinuation of treatment.
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