Chloramines refer to derivatives of
ammonia and organic
amines wherein one or more N−H bonds have been replaced by N−Cl bonds.[1][2] Two classes of compounds are considered: inorganic chloramines and organic chloramines. Chloramines are the most widely used members of the halamines.[3]
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.[4]
Organic chloramines
Organic chloramines feature the NCl
functional group attached to an organic substituent. Examples include N-chloromorpholine (ClN(CH2CH2)2O), N-chloropiperidine, and N-chloroquinuclidinium chloride.[7]
Chloramines are commonly produced by the action of
sodium hypochlorite on secondary amines:
Chloramines are formed by reaction of chlorine used to disinfect
swimming pools with ammonia and urea introduced into the pools by human perspiration, saliva, mucus, urine, and other biologic substances, and by insects and other pests.[9] Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools, as well as for skin, eye, and respiratory irritation.[10]
^Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo Reagents". Chemical Reviews. 78: 65–79.
doi:
10.1021/cr60311a005.
^Lindsay Smith, J. R.; McKeer, L. C.; Taylor, J. M. "4-Chlorination of Electron-Rich Benzenoid Compounds: 2,4-Dichloromethoxybenzene". Organic Syntheses. 67: 222.
doi:
10.15227/orgsyn.067.0222.
^Herranz, Eugenio; Sharpless, K. Barry (1983). "Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate". Org. Synth. 61: 93.
doi:
10.15227/orgsyn.061.0093.