Chloronitramide anion, also known as chloro(nitro)azanide, is a recently identified chemical byproduct of the disinfectant chloramine.[1][2][3] It is present in the tap water of about 113 million people.[1] Its toxicity has not been determined.[2] First observed and determined to be a degradation byproduct of chloramine in the early 1980s,[4] its molecular formula and structure were finally identified in a paper published November 2024.[5]

Chloronitramide anion

Structural diagram

Spacefill diagram
Names
IUPAC name
Chloro(nitro)azanide
Other names
Chloronitramide anion
Identifiers
3D model (JSmol)
  • InChI=1S/ClN2O2/c1-2-3(4)5/q-1
    Key: BPBMHZVBNAGSRE-UHFFFAOYSA-N
  • [N-]([N+](=O)[O-])Cl
Properties
ClN2O2-
Molar mass 95.46 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Research

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Chloronitramide anion was first detected as a UV absorbance interference during monitoring of chloramine and dichloramine in 1981.[4] It was then shown to form during the decomposition of both chemicals.[4] It was shown to likely be an anion in 1990.[6]

The structure of the molecule was identified by first determining its molecular formula to be ClN2O2-1 through high-resolution mass spectrometry, creating a candidate structure for the molecule, and verifying the correctness of the structure through nuclear magnetic resonance spectroscopy.[7]

Formation

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The identifying paper proposes chloronitramide to be formed through the reaction of chloramine (or dichloramine, which forms in chloramine solution) with NO2+, one of its degradation products. The formation of NO2+ begins when dichloramine (NH2Cl) hydrolyzes to form nitroxyl (HNO), which then reacts with dissolved oxygen (O2) to form the unstable peroxynitrite (ONOOH). NO2+ is one of the several reactive nitrogen species peroxynitrite then degrades to. The chloronitramide formed in this way then dissociates, losing the hydrogen, to form the anion.[4][8]

References

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  1. ^ a b Christensen, Jen (2024-11-21). "Solving a 40-year mystery, scientists ID chemical found in millions of Americans' tap water". CNN. Retrieved 2024-11-21.
  2. ^ a b Achenbach, Joel; Johnson, Carolyn Y. (2024-11-21). "Mysterious chemical byproduct in U.S. tap water finally identified". Washington Post. Retrieved 2024-11-22.
  3. ^ "Newly identified chemical in drinking water is likely in many homes and could be toxic, study finds". NBC News. 2024-11-21. Retrieved 2024-11-21.
  4. ^ a b c d Fairey, Julian L.; Laszakovits, Juliana R.; Pham, Huong T.; Do, Thien D.; Hodges, Samuel D.; McNeill, Kristopher; Wahman, David G. (2024-11-22). "Chloronitramide anion is a decomposition product of inorganic chloramines". Science. 386 (6724): 882–887. doi:10.1126/science.adk6749. ISSN 0036-8075. PMID 39571006.
  5. ^ "Mystery chemical in drinking water identified". Chemical & Engineering News. 2024-11-21. Retrieved 2024-11-21.
  6. ^ Leung, Solomon W.; Valentine, Richard L. (June 1994). "An unidentified chloramine decomposition product—I. Chemistry and characteristics". Water Research. 28 (6): 1475–1483. doi:10.1016/0043-1354(94)90316-6.
  7. ^ McCurry, Daniel L. (2024-11-22). "The chloramine dilemma". Science. 386 (6724): 851–852. doi:10.1126/science.adt8921. ISSN 0036-8075. PMID 39571038.
  8. ^ Wogan, Tim. "First detected 40 years ago, a byproduct in chloraminated drinking water has finally been identified". Chemistry World. Retrieved 2024-11-22.