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Chloronitramide anion

From Wikipedia, the free encyclopedia
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).

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 in the United States of America.[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]

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 a combination of ion chromatography and high-resolution mass spectrometry, creating a candidate structure for the molecule, and verifying the correctness of the structure through nuclear magnetic resonance spectroscopy.[1][7]

Ion chromatography, a method of separating ions and ionizable polar molecules, was used to separate the chloronitramide anion from the many salts present in samples containing it, which otherwise made if very difficult to apply mass spectrometry to the problem.[1] For scale, the samples were higher in salinity than salt water.[1][why?]

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 c d e 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.