Chloramines
Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds.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. Chloramines are the most widely used members of the halamines.
Inorganic chloramines
Inorganic chloramines comprise three compounds: monochloramine, dichloramine, and nitrogen trichloride. Monochloramine is of broad significance as a disinfectant for water.Inorganic chloramines are produced by the reaction of ammonia and hypochlorous acid or chlorine. An urban legend claims that mixing household bleach with ammonia-based cleaners releases chlorine gas or mustard gas; in reality, the gas produced by the reaction is a mixture of inorganic chloramines.
Organic chloramines
[image:N-chloropiperidine.png|thumb|144px|N-Chloropiperidine is a rare example of an organic chloramine.]image:Chloramine T.svg|thumb|144px|Chloramine-T is often referred to as a chloramine, but it is really a salt derived from a chloramine.
Organic chloramines feature the NCl functional group attached to an organic substituent. The simplest organic chloramine is N-chloromethylamine, ; notable examples include N-chloromorpholine, N-chloropiperidine, and N-chloroquinuclidinium chloride.
Chloramines are commonly produced by the action of sodium hypochlorite on secondary amines:
Tert-butyl hypochlorite can be used instead of bleach:
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 imines.