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Nitrogen trichloride

From Wikipedia, the free encyclopedia
Chemical compound
Nitrogen trichloride
Structural formula of nitrogen trichloride
Structural formula of nitrogen trichloride
Space-filling model of nitrogen trichloride
Space-filling model of nitrogen trichloride
  Nitrogen, N
  Chlorine, Cl
Nitrogen trichloride
Nitrogen trichloride
Names
Other names
Trichloramine
Agene
Nitrogen(III) chloride
Trichloroazane
Trichlorine nitride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.030.029Edit this at Wikidata
EC Number
  • 233-045-1
1840
RTECS number
  • QW974000
UNII
  • InChI=1S/Cl3N/c1-4(2)3 checkY
    Key: QEHKBHWEUPXBCW-UHFFFAOYSA-N checkY
  • InChI=1/Cl3N/c1-4(2)3
    Key: QEHKBHWEUPXBCW-UHFFFAOYAZ
  • ClN(Cl)Cl
Properties
NCl3
Molar mass120.36 g·mol−1
Appearanceyellow oily liquid
Odorchlorine-like
Density1.653 g/mL
Melting point−40 °C (−40 °F; 233 K)
Boiling point71 °C (160 °F; 344 K)
immiscible
slowly decomposes
Solubilitysoluble inbenzene,chloroform,CCl4,CS2,PCl3
Structure
orthorhombic (below −40 °C)
trigonal pyramidal
0.6D
Thermochemistry
232 kJ/mol
Hazards
NFPA 704 (fire diamond)
93 °C (199 °F; 366 K)
Related compounds
Otheranions
Nitrogen trifluoride
Nitrogen tribromide
Nitrogen triiodide
Othercations
Phosphorus trichloride
Arsenic trichloride
Monochloramine
Dichloramine
Related compounds
Nitrosyl chloride
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Nitrogen trichloride, also known astrichloramine, is thechemical compound with theformulaNCl3. This yellow, oily, and explosive liquid is most commonly encountered as a product ofchemical reactions betweenammonia-derivatives andchlorine (for example, inswimming pools). Alongsidemonochloramine anddichloramine, trichloramine is responsible for the distinctive 'chlorine smell' associated with swimming pools, where the compound is readily formed as a product fromhypochlorous acid reacting withammonia and other nitrogenous substances in the water, such asurea fromurine.[1]

Preparation and occurrence

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The compound is generated by treatment ofammonium chloride withcalcium hypochlorite. When prepared in an aqueous-dichloromethane mixture, the trichloramine is extracted into the nonaqueous phase.[2] Intermediates in this conversion includemonochloramine anddichloramine,NH2Cl andNHCl2, respectively.

Nitrogen trichloride, trademarked asAgene, was at one time used to bleachflour,[3] but this practice was banned in the United States in 1949 due to safety concerns.

Structure and properties

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Like ammonia,NCl3 is apyramidal molecule. The N-Cl distances are 1.42 Å, and the Cl-N-Cl angles are 107°.[4]

Nitrogen trichloride can form in small amounts when public water supplies are disinfected withmonochloramine, and in swimming pools by disinfecting chlorine reacting withurea in urine and sweat from bathers.

Reactions and uses

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The chemistry ofNCl3 has been well explored.[5] It is moderatelypolar with adipole moment of 0.6 D. The nitrogen center is basic but much less so than ammonia. It ishydrolyzed by hot water to releaseammonia andhypochlorous acid.

NCl3+3H2ONH3+3HCl+32O2{\displaystyle {\ce {NCl3 + 3H2O -> NH3 + 3HCl + 3/2O2}}}

Concentrated samples of NCl3 can explode to giveN2 andchlorine gas.[citation needed]

2NCl3N2+3Cl2{\displaystyle {\ce {2NCl3 -> N2 + 3Cl2}}}

In the presence ofaluminium trichloride, NCl3 reacts with some branched hydrocarbons to produce, after a hydrolysis step,amines.[2][6]

Safety

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Nitrogen trichloride can irritate mucousmembranes — it is alachrymatory agent, but has never been used as such.[7][8] The compound (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 several fingers and an eye in two explosions.[9] In 1813, anNCl3 explosion blinded SirHumphry Davy temporarily, inducing him to hireMichael Faraday as a co-worker. They were both injured in anotherNCl3 explosion shortly thereafter.[10]

See also

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References

[edit]
  1. ^"Chloramines: Understanding "Pool Smell"".American Chemistry Council. July 2006. Archived fromthe original on 17 December 2019. Retrieved17 December 2019.
  2. ^abKovacic, Peter; Chaudhary, Sohan S. (1968). "1-Amino-1-Methylcyclohexane".Organic Syntheses.48: 4.doi:10.15227/orgsyn.048.0004.
  3. ^Hawthorn, J.; Todd, J. P. (1955). "Some effects of oxygen on the mixing of bread doughs".Journal of the Science of Food and Agriculture.6 (9):501–511.Bibcode:1955JSFA....6..501H.doi:10.1002/jsfa.2740060906.
  4. ^Holleman, A. F.; Wiberg, E. (2001).Inorganic Chemistry. San Diego: Academic Press.ISBN 978-0-12-352651-9.
  5. ^Greenwood, Norman N.; Earnshaw, Alan (1997).Chemistry of the Elements (2nd ed.).Butterworth-Heinemann.doi:10.1016/C2009-0-30414-6.ISBN 978-0-08-037941-8.
  6. ^Kovacic, Peter; Goralski, Christian T.; Hiller, John J.; Levisky, Joseph A.; Lange, Richard M. (March 20, 1965)."Amination of Toluene with Trichloramine-Lewis Acid Catalyst".Journal of the American Chemical Society.87 (6):1262–1266.doi:10.1021/ja01084a021.ISSN 0002-7863.
  7. ^White, G. C. (1999).The Handbook of Chlorination and Alternative Disinfectants (4th ed.). Wiley. p. 322.ISBN 978-0-471-29207-4.
  8. ^"Health Hazard Evaluation Report: Investigation of Employee Symptoms at an Indoor Water Park"(PDF).NIOSH ENews.6 (4). August 2008. HETA 2007-0163-3062.
  9. ^Thénard J. L.;Berthollet C. L. (1813). "Report on the work of Pierre Louis Dulong".Annales de Chimie et de Physique.86 (6):37–43.
  10. ^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.

Further reading

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  • Jander, J. (1976). "Recent Chemistry and Structure Investigation of Nitrogen Triiodide, Tribromide, Trichloride, and Related Compounds".Advances in Inorganic Chemistry. Advances in Inorganic Chemistry and Radiochemistry.19:1–63.doi:10.1016/S0065-2792(08)60070-9.ISBN 9780120236190.
  • Kovacic, P.; Lowery, M. K.; Field, K. W. (1970). "Chemistry of N-Bromamines and N-Chloramines".Chemical Reviews.70 (6):639–665.doi:10.1021/cr60268a002.
  • Hartl, H.; Schöner, J.; Jander, J.; Schulz, H. (1975). "Die Struktur des Festen Stickstofftrichlorids (−125 °C)".Zeitschrift für Anorganische und Allgemeine Chemie.413 (1):61–71.doi:10.1002/zaac.19754130108.
  • Cazzoli, G.; Favero, P. G.; Dal Borgo, A. (1974). "Molecular Structure, Nuclear Quadrupole Coupling Constant and Dipole Moment of Nitrogen Trichloride from Microwave Spectroscopy".Journal of Molecular Spectroscopy.50 (1–3):82–89.Bibcode:1974JMoSp..50...82C.doi:10.1016/0022-2852(74)90219-7.
  • Bayersdorfer, L.; Engelhardt, U.; Fischer, J.; Höhne, K.; Jander, J. (1969). "Untersuchungen an Stickstoff–Chlor-Verbindungen. V. Infrarot- und RAMAN-Spektren von Stickstofftrichlorid".Zeitschrift für Anorganische und Allgemeine Chemie.366 (3–4):169–179.doi:10.1002/zaac.19693660308.

External links

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Nitrogen species
Hydrides
Organic
Oxides
Halides
Oxidation states
−3,−2,−1, 0,+1,+2,+3,+4,+5 (a stronglyacidic oxide)
Chlorides andacids
Chlorine fluorides
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Chlorineoxyfluorides
Chlorine(I) derivatives
Salts and covalent derivatives of thenitride ion
Salts and covalent derivatives of thechloride ion
HClHe
LiClBeCl2B4Cl4
B12Cl12
BCl3
B2Cl4
+BO3
C2Cl2
C2Cl4
C2Cl6
CCl4
+C
+CO3
NCl3
ClN3
+N
+NO3
ClxOy
Cl2O
Cl2O2
ClO
ClO2
Cl2O4
Cl2O6
Cl2O7
ClO4
+O
ClF
ClF3
ClF5
Ne
NaClMgCl2AlCl
AlCl3
Si5Cl12
Si2Cl6
SiCl4
P2Cl4
PCl3
PCl5
+P
S2Cl2
SCl2
SCl4
+SO4
Cl2Ar
KClCaCl
CaCl2
ScCl3TiCl2
TiCl3
TiCl4
VCl2
VCl3
VCl4
VCl5
CrCl2
CrCl3
CrCl4
MnCl2
MnCl3
FeCl2
FeCl3
CoCl2
CoCl3
NiCl2CuCl
CuCl2
ZnCl2GaCl
GaCl3
GeCl2
GeCl4
AsCl3
AsCl5
+As
Se2Cl2
SeCl2
SeCl4
BrClKr
RbClSrCl2YCl3ZrCl2
ZrCl3
ZrCl4
NbCl3
NbCl4
NbCl5
MoCl2
MoCl3
MoCl4
MoCl5
MoCl6
TcCl3
TcCl4
RuCl2
RuCl3
RuCl4
RhCl3PdCl2AgClCdCl2InCl
InCl2
InCl3
SnCl2
SnCl4
SbCl3
SbCl5
Te3Cl2
TeCl2
TeCl4
ICl
ICl3
XeCl
XeCl2
XeCl4
CsClBaCl2*LuCl3
177LuCl3
HfCl4TaCl3
TaCl4
TaCl5
WCl2
WCl3
WCl4
WCl5
WCl6
ReCl3
ReCl4
ReCl5
ReCl6
OsCl2
OsCl3
OsCl4
OsCl5
IrCl2
IrCl3
IrCl4
PtCl2
PtCl4
PtCl2−6
AuCl
(Au[AuCl4])2
AuCl3
AuCl4
Hg2Cl2
HgCl2
TlCl
TlCl3
PbCl2
PbCl4
BiCl3PoCl2
PoCl4
AtClRn
FrClRaCl2**LrCl3RfCl4DbCl5SgO2Cl2BhO3ClHsMtDsRgCnNhFlMcLvTsOg
 
*LaCl3CeCl3PrCl3NdCl2
NdCl3
PmCl3SmCl2
SmCl3
EuCl2
EuCl3
GdCl3TbCl3DyCl2
DyCl3
HoCl3ErCl3TmCl2
TmCl3
YbCl2
YbCl3
**AcCl3ThCl3
ThCl4
PaCl4
PaCl5
UCl3
UCl4
UCl5
UCl6
NpCl3
NpCl4
PuCl3
PuCl4
PuCl2−6
AmCl2
AmCl3
CmCl3BkCl3CfCl3
CfCl2
EsCl2
EsCl3
FmCl2MdCl2NoCl2
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