Chloramines refer to derivatives of

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

and organic

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s wherein one or more N−H bonds have been replaced by N−Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines. Chloramines are the most widely used members of the halamines.

Inorganic chloramines

Inorganic chloramines comprise three compounds: monochloramine (NH₂Cl), dichloramine (NHCl₂), and nitrogen trichloride (NCl₃). Monochloramine is of broad significance as a disinfectant for water. Inorganic chloramines are produced by the reaction of

and

hypochlorous acid Hypochlorous acid is an inorganic compound with the chemical formula , also written as HClO, HOCl, or ClHO. Its structure is . It is an acid that forms when chlorine dissolves in water, and itself partially dissociates, forming a hypochlorite an ...

chlorine Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...

. An

urban legend Urban legend (sometimes modern legend, urban myth, or simply legend) is a genre of folklore concerning stories about an unusual (usually scary) or humorous event that many people believe to be true but largely are not. These legends can be e ...

claims that mixing household bleach (aqueous

sodium hypochlorite Sodium hypochlorite is an alkaline inorganic chemical compound with the formula (also written as NaClO). It is commonly known in a dilute aqueous solution as bleach or chlorine bleach. It is the sodium salt of hypochlorous acid, consisting of ...

) with ammonia-based cleaners releases chlorine gas or

mustard gas Mustard gas or sulfur mustard are names commonly used for the organosulfur compound, organosulfur chemical compound bis(2-chloroethyl) sulfide, which has the chemical structure S(CH2CH2Cl)2, as well as other Chemical species, species. In the wi ...

; in reality, the gas produced by the reaction is a mixture of inorganic chloramines.

Organic chloramines

144px, ''N''-Chloropiperidine is a rare example of an organic chloramine. 144px, Chloramine-T is often referred to as a chloramine, but it is really a salt (CH₃C₆H₄SO₂NClNa) derived from a chloramine. Organic chloramines feature the NCl

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

attached to an organic substituent. The simplest organic chloramine is ''N''-chloromethylamine, CH3NHCl; notable examples include ''N''-chloromorpholine (ClN(CH₂CH₂)₂O), ''N''-chloropiperidine, and ''N''-chloroquinuclidinium chloride. Chloramines are commonly produced by the action of

on secondary amines: :R₂NH + NaOCl → R₂NCl + NaOH ''Tert''-butyl hypochlorite can be used instead of bleach: :R₂NH + t-BuOCl → R₂NCl + t-BuOH Very few chloramines are stable, and they easily decompose. In acid, they homolyze in the Hofmann–Löffler reaction; in base, they eliminate to the corresponding

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

Swimming pools

Chloramines are formed by reaction of chlorine used to disinfect

swimming pool A swimming pool, swimming bath, wading pool, paddling pool, or simply pool, is a structure designed to hold water to enable Human swimming, swimming and associated activities. Pools can be built into the ground (in-ground pools) or built abo ...

s with ammonia and urea introduced into the pools by human perspiration, saliva, mucus, urine, and other biologic substances, and by insects and other pests. Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools, as well as for skin, eye, and respiratory irritation.

References

{{Authority control Nitrogen–halogen compounds Swimming pools