Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds.[1][2] Two classes of compounds are considered: inorganic chloramines and organic chloramines.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]
N-Chloropiperidine is a rare example of an organic chloramine.[5]Chloramine-T is often referred to as a chloramine, but it is really a salt (CH3C6H4SO2NClNa) derived from a chloramine.[6]
Organic chloramines feature the NCl functional group attached to an organic substituent. The simplest organic chloramine is N-chloromethylamine, CH3NHCl;[7] notable examples include N-chloromorpholine (ClN(CH2CH2)2O), N-chloropiperidine, and N-chloroquinuclidinium chloride.[8]
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.[10] Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools, as well as for skin, eye, and respiratory irritation.[11]
^Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo Reagents". Chemical Reviews. 78: 65–79. doi:10.1021/cr60311a005.
^Heeb, Michèle B.; Kristiana, Ina; Trogolo, Daniela; Arey, J. Samuel; von Gunten, Urs (2017). "Formation and reactivity of inorganic and organic chloramines and bromamines during oxidative water treatment". Water Research. 110: 91–101. doi:10.1016/j.watres.2016.11.065. PMID27998787.
^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.
