Chloramines

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description Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds.[1][2] Two classes of compounds are considered: inorganic chloramines and organic chloramines.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

Inorganic chloramines are produced by the reaction of ammonia and hypochlorous acid or chlorine. An urban legend claims that mixing household bleach (aqueous sodium hypochlorite) 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

File:N-chloropiperidine.png
N-Chloropiperidine is a rare example of an organic chloramine.[5]
File:Chloramine T.svg
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, Page Module:Chem2/styles.css has no content.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:

R2NH + NaOCl → R2NCl + NaOH

Tert-butyl hypochlorite can be used instead of bleach:[9]

R2NH + t-BuOCl → R2NCl + t-BuOH

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.

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.[10] Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools,[11] as well as for skin, eye, and respiratory irritation.[12]

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Berliner, J. F. T. (1931). "The Chemistry of Chloramines" (PDF). American Water Works Association. 23 (9): 1320−1333. doi:10.1002/j.1551-8833.1931.tb17955.x. JSTOR 41228138. Archived from the original on 2 October 2025. Retrieved 4 October 2023.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Kovacic, Peter; Lowery, Michael K.; Field, Kurt W. (1970). "Chemistry of N-bromamines and N-chloramines". Chemical Reviews. 70 (6): 639−665. doi:10.1021/cr60268a002. Retrieved 4 October 2023.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Dong, Alideertu; Wang, Yan-Jie; Gao, Yangyang; Gao, Tianyi; Gao, Ge (2017). "Chemical Insights into Antibacterial N -Halamines". Chemical Reviews. 117 (6): 4806–4862. doi:10.1021/acs.chemrev.6b00687. PMID 28252944.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Lawrence, Stephen A. (2004). Amines: Synthesis, Properties and Applications. Cambridge University Press. p. 172. ISBN 9780521782845.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Claxton, George P.; Allen, Lloyd; Grisar, J. Martin (1977). "2,3,4,5-Tetrahydropyridine Trimer". Organic Syntheses. 56: 118. doi:10.15227/orgsyn.056.0118.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo Reagents". Chemical Reviews. 78: 65–79. doi:10.1021/cr60311a005.
  7. ^ Page Module:Citation/CS1/styles.css has no content.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. PMID 27998787.
  8. ^ Page Module:Citation/CS1/styles.css has no content.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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content."Controlling Chloramines in Indoor Swimming Pools". NSW Government Health. 3 December 2012. Retrieved 20 February 2013.
  11. ^ Page Module:Citation/CS1/styles.css has no content."Chloramines: Understanding "Pool Smell"". American Chemistry Council. July 2006. Archived from the original on 17 December 2019. Retrieved 17 December 2019.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Bessonneau, Vincent; Derbez, Mickaël; Clément, Michel; Thomas, Olivier (2011). "Determinants of chlorination by-products in indoor swimming pools". International Journal of Hygiene and Environmental Health. 215 (1): 76–85. doi:10.1016/j.ijheh.2011.07.009. ISSN 1438-4639. PMID 21862402.

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