Chloramines refer to derivatives of
ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...
and organic amines wherein one or more N-H bonds have been replaced by N-Cl bonds.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.
Inorganic chloramines
Inorganic chloramines comprise three compounds:
monochloramine (NH
2Cl),
dichloramine
Dichloramine is a reactive inorganic compound. It has the formula . The yellow gas is unstable and reacts with many materials. It is formed by a reaction between ammonia and chlorine or sodium hypochlorite. It is a byproduct formed during the synth ...
(NHCl
2), and
nitrogen trichloride (NCl
3). Monochloramine is of broad significance as a disinfectant for water.
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 (CH
3C
6H
4SO
2NClNa) derived from a chloramine.
Organic chloramines feature the NCl
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...
attached to an organic substituent. Examples include ''N''-chloromorpholine (ClN(CH
2CH
2)
2O), ''N''-chloropiperidine, and ''N''-chloroquinuclidinium chloride.
Chloramines are commonly produced by the action of
bleach on secondary amines:
:R
2NH + NaOCl → R
2NCl + NaOH
''Tert''-butyl hypochlorite can be used instead of bleach:
:R
2NH + t-BuOCl → R
2NCl + t-BuOH
Swimming pools
Chloramines also refers to any chloramine formed by chlorine reacting with ammonia introduced into
swimming pools by human perspiration, saliva, mucus, urine, and other biologic substances, and by insects and other pests.
Chloramines are responsible for the "chlorine smell" of pools, as well as skin and eye irritation. These problems are the result of insufficient levels of free available chlorine.
References
{{Reflist, 2
Nitrogen halides
Swimming pools
