Chloramines

Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds.[1][2] Two classes of compounds are considered: inorganic chloramines and organic chloramines.

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.[3]

Organic chloramines
N-Chloropiperidine is a rare example of an organic chloramine.[4]
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.[6]

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:[7]

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.[8] Chloramines, especially trichloramine, are responsible for most of the "chlorine smell" of pools, as well as for skin, eye, and respiratory irritation.[9]

References
  1. Berliner, J. F. T. (1931). "The Chemistry of Chloramines". American Water Works Association. 23 (9): 1320−1333. Retrieved 4 October 2023.
  2. Kovacic, Peter; Lowery, Michael K.; Field, Kurt W. (1970). "Chemistry of N-bromamines and N-chloramines". Chemical Reviews. 70 (6): 639−665. Retrieved 4 October 2023.
  3. Lawrence, Stephen A. (2004). Amines: Synthesis, Properties and Applications. Cambridge University Press. p. 172. ISBN 9780521782845.
  4. 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.
  5. Campbell, Malcolm M.; Johnson, Graham. (1978). "Chloramine T and Related N-halogeno-N-metallo Reagents". Chemical Reviews. 78: 65–79. doi:10.1021/cr60311a005.
  6. 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.; Collective Volume, vol. 8, p. 167
  7. 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.
  8. "Controlling Chloramines in Indoor Swimming Pools". NSW Government Health. 3 December 2012. Retrieved 20 February 2013.
  9. 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: 76-85. doi:10.1016/j.ijheh.2011.07.009. ISSN 1438-4639.
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