Chloramines Explained

Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds.[1] [2] Two classes of compounds are considered: inorganic chloramines and organic chloramines.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

thumb|144px|N-Chloropiperidine is a rare example of an organic chloramine.thumb|144px|Chloramine-T is often referred to as a chloramine, but it is really a salt (CH3C6H4SO2NClNa) derived from a chloramine.[5]

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.

Chloramines are commonly produced by the action of sodium hypochlorite on secondary amines:

R2NH + NaOCl → R2NCl + NaOHTert-butyl hypochlorite can be used instead of bleach:[6]

R2NH + t-BuOCl → R2NCl + t-BuOH

Swimming pools

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.[7] Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools, as well as for skin, eye, and respiratory irritation.[8]

Notes and References

  1. Berliner . J. F. T. . The Chemistry of Chloramines . American Water Works Association . 1931 . 23 . 9 . 1320−1333 . 10.1002/j.1551-8833.1931.tb17955.x . 41228138 . 4 October 2023.
  2. Kovacic . Peter . Lowery . Michael K. . Field . Kurt W. . Chemistry of N-bromamines and N-chloramines . Chemical Reviews . 1970 . 70 . 6 . 639−665 . 10.1021/cr60268a002 . 4 October 2023.
  3. 10.1021/acs.chemrev.6b00687 . Chemical Insights into Antibacterial N -Halamines . 2017 . Dong . Alideertu . Wang . Yan-Jie . Gao . Yangyang . Gao . Tianyi . Gao . Ge . Chemical Reviews . 117 . 6 . 4806–4862 . 28252944 .
  4. Book: Lawrence. Stephen A.. Amines: Synthesis, Properties and Applications. 2004. Cambridge University Press. 9780521782845. 172. en.
  5. 10.1021/cr60311a005. Chloramine T and Related N-halogeno-N-metallo Reagents. Chemical Reviews. 78. 65–79. 1978. Campbell. Malcolm M.. Johnson. Graham..
  6. Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate. Eugenio. Herranz. K. Barry. Sharpless. Org. Synth.. 1983. 61. 93. 10.15227/orgsyn.061.0093.
  7. Web site: Controlling Chloramines in Indoor Swimming Pools. NSW Government Health. 20 February 2013. 3 December 2012.
  8. Bessonneau . Vincent . Derbez . Mickaël . Clément . Michel . Thomas . Olivier . Determinants of chlorination by-products in indoor swimming pools . International Journal of Hygiene and Environmental Health . 2011 . 215 . 1 . 76–85 . 1438-4639 . 10.1016/j.ijheh.2011.07.009 . 21862402 .

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