Nitrogen trichloride

Nitrogen trichloride
Structural formula of nitrogen trichloride	Space-filling model of nitrogen trichloride
Names
	Other names Trichloramine; Agene; Nitrogen(III) chloride; Trichloroazane; Trichlorine nitride
Identifiers
CAS Number	10025-85-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37382 ;
ChemSpider	55361 ;
ECHA InfoCard	100.030.029
EC Number	233-045-1;
PubChem CID	61437;
RTECS number	QW974000;
CompTox Dashboard (EPA)	DTXSID4074938 ;
	InChI InChI=1S/Cl3N/c1-4(2)3 Key: QEHKBHWEUPXBCW-UHFFFAOYSA-N ; InChI=1/Cl3N/c1-4(2)3 Key: QEHKBHWEUPXBCW-UHFFFAOYAZ;
	SMILES ClN(Cl)Cl;
Properties
Chemical formula	Cl3N
Molar mass	120.36 g·mol−1
Appearance	yellow oily liquid
Odor	chlorine-like
Density	1.653 g/mL
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	71 °C (160 °F; 344 K)
Solubility in water	immiscible; slowly decomposes
Solubility	soluble in benzene, chloroform, CCl4, CS2, PCl3
Structure
Crystal structure	orthorhombic (below −40 °C)
Molecular shape	trigonal pyramidal
Dipole moment	0.6 D
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	232 kJ/mol
Hazards
NFPA 704 (fire diamond)	2 0 4 OX
Autoignition; temperature	93 °C (199 °F; 366 K)
Related compounds
Other anions	Nitrogen trifluoride; Nitrogen tribromide; Nitrogen triiodide
Other cations	Phosphorus trichloride; Arsenic trichloride
Related chloramines	Chloramine; Dichloramine
Related compounds	Nitrosyl chloride
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Nitrogen trichloride, also known as trichloramine, is the chemical compound with the formula NCl₃. This yellow, oily, pungent-smelling liquid is most commonly encountered as a byproduct of chemical reactions between ammonia-derivatives and chlorine (for example, in swimming pools).

Preparation and structure

The compound is prepared by treatment of ammonium salts, such as ammonium nitrate with chlorine.

Intermediates in this conversion include chloramine and dichloramine, NH₂Cl and NHCl₂, respectively.

Like ammonia, NCl₃ is a pyramidal molecule. The N-Cl distances are 1.76 Å, and the Cl-N-Cl angles are 107°.^[1]

Nitrogen trichloride can form in small amounts when public water supplies are disinfected with monochloramine, and in swimming pools by disinfecting chlorine reacting with urea in urine from bathers. Nitrogen trichloride, trademarked as Agene, was used to artificially bleach and age flour, but was banned in 1949: In humans Agene was found to cause severe and widespread neurological disorders leading to its banning in 1947. Dogs that ate bread made from treated flour suffered epileptic-like fits; the toxic agent was methionine sulfoximine.^[2]

Reactions

Despite the similarities of the Pauling electronegativities of nitrogen and chlorine, this molecule has moderate polarity with negative charges residing on nitrogen. So the nitrogen in NCl₃ is often considered to have the +3 oxidation state and the chlorine atoms are considered to be in the -1 oxidation state.
It is hydrolyzed by hot water to release ammonia and hypochlorous acid.

NCl₃ + 3 H₂O → NH₃ + 3 HOCl

Safety

Nitrogen trichloride can irritate mucous membranes—it is a lachrymatory agent, but has never been used as such.^[3]^[4] The pure substance (rarely encountered) is a dangerous explosive, being sensitive to light, heat, even moderate shock, and organic compounds. Pierre Louis Dulong first prepared it in 1812, and lost two fingers and an eye in two explosions. In 1813, an NCl₃ explosion blinded Sir Humphry Davy temporarily, inducing him to hire Michael Faraday as a co-worker. They were both injured in another NCl₃ explosion shortly thereafter.^[5]

References

^ Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. ISBN 0-12-352651-5.{{cite book}}: CS1 maint: multiple names: authors list (link)
^ Shaw, CA; Bains, JS (1998). "Did consumption of flour bleached by the agene process contribute to the incidence of neurological disease?". Medical Hypotheses. 51 (6): 477–81. doi:10.1016/S0306-9877(98)90067-6. PMID 10052866.
^ White, G. C. (1999). The Handbook of Chlorination and Alternative Disinfectants (4th ed.). Wiley. p. 322. ISBN 978-0-471-29207-4.
^ "Health Hazard Evaluation Report: Investigation of Employee Symptoms at an Indoor Water Park" (pdf). NIOSH eNews. 6 (4). National Institute for Occupational Safety and Health. August 2008. HETA 2007-0163-3062.
^ Thomas, J.M. (1991). Michael Faraday and The Royal Institution: The Genius of Man and Place (PBK). CRC Press. p. 17. ISBN 978-0-7503-0145-9.

External links

[1] Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. ISBN 0-12-352651-5.{{cite book}}: CS1 maint: multiple names: authors list (link)

[2] Shaw, CA; Bains, JS (1998). "Did consumption of flour bleached by the agene process contribute to the incidence of neurological disease?". Medical Hypotheses. 51 (6): 477–81. doi:10.1016/S0306-9877(98)90067-6. PMID 10052866.

[3] White, G. C. (1999). The Handbook of Chlorination and Alternative Disinfectants (4th ed.). Wiley. p. 322. ISBN 978-0-471-29207-4.

[4] "Health Hazard Evaluation Report: Investigation of Employee Symptoms at an Indoor Water Park" (pdf). NIOSH eNews. 6 (4). National Institute for Occupational Safety and Health. August 2008. HETA 2007-0163-3062.

[Thomas1991-5] Thomas, J.M. (1991). Michael Faraday and The Royal Institution: The Genius of Man and Place (PBK). CRC Press. p. 17. ISBN 978-0-7503-0145-9.

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