Phosphoramide is a
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the molecular formula O=P(NH
2)
3. It is a
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...
of
phosphoric acid
Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, w ...
in which each of the
hydroxyl groups
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
have been replaced with an
amino group
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such a ...
. Phosphoramide arises from the reaction of phosphoryl chloride with ammonia. It is a white solid that is soluble in
polar solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...
s. In moist air, it hydrolyzes to an ammonium salt:
:2 H
2O + OP(NH
2)
3 → NH
4+ PO3(NH2) + NH
3
It reacts with sodium hydroxide with loss of
ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...
:
:NaOH + OP(NH
2)
3 → NaO
2P(NH
2)
2 + NH
3
The related thiophosphoryl compound P(=S)(NH
2)
3 was made from the reaction of
thiophosphoryl chloride
Thiophosphoryl chloride is an inorganic compound with the formula PSCl3.Spilling, C. D. "Thiophosphoryl Chloride" in Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons, Weinheim, 2001. . Article Online Posting Date: April 15, 2001. ...
with ammonia.
Phosphoramides
Phosphoramide is also the parent compound for a range of derivatives called phosphoramides.
An example compound is the polar solvent
hexamethylphosphoramide
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is a useful reagent in organic synthesis.
Structure and reactivity
HMPA is the oxide of the highly basic t ...
(HMPA).
References
External links
*
*
{{Organophosphorus
Functional groups