Phosphoramide

Phosphoramide
Names
	IUPAC name Phosphoric triamide
	Other names Diaminophosphorylamine; Phosphoric amide; Phosphoryl triamide; Triaminophosphine oxide;
Identifiers
CAS Number	13597-72-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	109920;
PubChem CID	123317;
UNII	M27WLZ6CWP ;
CompTox Dashboard (EPA)	DTXSID40159607 ;
	InChI InChI=1S/H6N3OP/c1-5(2,3)4/h(H6,1,2,3,4) Key: DMSZORWOGDLWGN-UHFFFAOYSA-N; InChI=1/H6N3OP/c1-5(2,3)4/h(H6,1,2,3,4) Key: DMSZORWOGDLWGN-UHFFFAOYAP;
	SMILES NP(=O)(N)N;
Properties
Chemical formula	O=P(NH2)3
Molar mass	95.042 g·mol−1
Appearance	white solid
Solubility in water	good
Acidity (pKa)	<3.6
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phosphoramide is a chemical compound with the molecular formula O=P(NH₂)₃. It is a derivative of phosphoric acid in which each of the hydroxyl groups have been replaced with an amino group. In bulk, the compound is a white solid which is soluble in polar solvents.

Chemical properties

Phosphoramide arises from the reaction of phosphoryl chloride with ammonia. In moist air, it hydrolyzes to an ammonium salt:

2 H₂O + O=P(NH₂)₃ → [NH₄]⁺[PO₂(OH)(NH₂)]⁻ + NH₃

It reacts with sodium hydroxide with loss of ammonia:^[2]

NaOH + O=P(NH₂)₃ → Na⁺[PO₂(NH₂)₂]⁻ + NH₃

The related thiophosphoryl triamide compound S=P(NH₂)₃ was made from the reaction of thiophosphoryl chloride with ammonia.

Phosphoramides

Phosphoramide is also the parent compound for a range of derivatives called phosphoramides.^[3] An example compound is the polar solvent hexamethylphosphoramide (HMPA).

References

^ Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 186. ISBN 0-08-029214-3. LCCN 82-16524.
^ Robert Klement; Otto Koch (1954). "Phosphoroxy‐triamid und Phosphorthio‐triamid". Chemische Berichte. 87 (3): 333–340. doi:10.1002/cber.19540870308.
^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "phosphoramides". doi:10.1351/goldbook.A00484

External links

Media related to phosphoramides at Wikimedia Commons
The dictionary definition of phosphoramide at Wiktionary

[P82db-1] Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 186. ISBN 0-08-029214-3. LCCN 82-16524.

[2] Robert Klement; Otto Koch (1954). "Phosphoroxy‐triamid und Phosphorthio‐triamid". Chemische Berichte. 87 (3): 333–340. doi:10.1002/cber.19540870308.

[3] IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "phosphoramides". doi:10.1351/goldbook.A00484

[1]

[2]

[3]