Phosphoramide

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Phosphoramide
Phosphoramide.svg
Names
IUPAC name
Phosphoric triamide
Other names
  • Diaminophosphorylamine
  • Phosphoric amide
  • Phosphoryl triamide
  • Triaminophosphine oxide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
  • NP(=O)(N)N
Properties
O=P(NH2)3
Molar mass 95.042 g·mol−1
Appearancewhite solid
good
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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, soluble in polar solvents.

Contents

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: [1]

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. [2] An example compound is the polar solvent hexamethylphosphoramide (HMPA).

Related Research Articles

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 Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction between an acid and a base

In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

<span class="mw-page-title-main">Ammonium</span> Polyatomic ion (NH₄, charge +1)

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.

<span class="mw-page-title-main">Base (chemistry)</span> Type of chemical substance

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century.

<span class="mw-page-title-main">Hydroxylamine</span> Inorganic compound

Hydroxylamine is an inorganic compound with the formula NH2OH. The material is a white crystalline, hygroscopic compound. Hydroxylamine is almost always provided and used as an aqueous solution. It is consumed almost exclusively to produce Nylon-6. The oxidation of NH3 to hydroxylamine is a step in biological nitrification.

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.

<span class="mw-page-title-main">Sodium amide</span> Chemical compound

Sodium amide, commonly called sodamide, is the inorganic compound with the formula NaNH2. It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagent. NaNH2 conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. NaNH2 has been widely employed as a strong base in organic synthesis.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Hemiaminal</span> Organic compound or group with a hydroxyl and amine attached to the same carbon

In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.

<span class="mw-page-title-main">Rhodium(III) chloride</span> Chemical compound

Rhodium(III) chloride refers to inorganic compounds with the formula RhCl3(H2O)n, where n varies from 0 to 3. These are diamagnetic solids featuring octahedral Rh(III) centres. Depending on the value of n, the material is either a dense brown solid or a soluble reddish salt. The soluble trihydrated (n = 3) salt is widely used to prepare compounds used in homogeneous catalysis, notably for the industrial production of acetic acid and hydroformylation.

<span class="mw-page-title-main">Sulfamic acid</span> Chemical compound

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.

<span class="mw-page-title-main">Triflic acid</span> Chemical compound

Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most common oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

<span class="mw-page-title-main">Hexachlorophosphazene</span> Chemical compound

Hexachlorophosphazene is an inorganic compound with the formula (NPCl2)3. The molecule has a cyclic, unsaturated backbone consisting of alternating phosphorus and nitrogen centers, and can be viewed as a trimer of the hypothetical compound N≡PCl2. Its classification as a phosphazene highlights its relationship to benzene. There is large academic interest in the compound relating to the phosphorus-nitrogen bonding and phosphorus reactivity.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

<span class="mw-page-title-main">Metal amides</span>

Metal amides (systematic name metal azanides) are a class of coordination compounds composed of a metal center with amide ligands of the form NR2. Amido complexes of the parent amido ligand NH2 are rare compared to complexes with diorganylamido ligand, such as dimethylamido. Amide ligands have two electron pairs available for bonding.

In chemistry, the amino radical, ·NH2, also known as the aminyl radical or azanyl radical, is the neutral form of the amide ion. Aminyl radicals are highly reactive and consequently short-lived, like most radicals; however, they form an important part of nitrogen chemistry. In sufficiently high concentration, amino radicals dimerise to form hydrazine. While NH2 as a functional group is common in nature, forming a part of many compounds, the radical cannot be isolated in its free form.

<span class="mw-page-title-main">Ammonium carbamate</span> Chemical compound

Ammonium carbamate is a chemical compound with the formula [NH4][H2NCO2] consisting of ammonium cation NH+4 and carbamate anion NH2COO. It is a white solid that is extremely soluble in water, less so in alcohol. Ammonium carbamate can be formed by the reaction of ammonia NH3 with carbon dioxide CO2, and will slowly decompose to those gases at ordinary temperatures and pressures. It is an intermediate in the industrial synthesis of urea (NH2)2CO, an important fertilizer.

<span class="mw-page-title-main">Phosphoramides</span>

Phosphoramides are a class of phosphorus compounds with the formula O=P(NR2)3-n(OH)n. They can be considered derivatives of phosphoric acid where OH groups have been replaced with an amino or R-substituted amino group. In practise the term is commonly confined to the phosphoric triamides (P(=O)(NR2)3), essentially phosphoramide and derivatives thereof. Derivatives with the general structures P(=O)(OH)(NR2)2 or P(=O)(OH)2(NR2) are usually referred to as phosphoramidic acids.

In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into . Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), or with inorganic compounds to produce nitrides. This reaction is analogous to hydrolysis in which water molecules are split. Similar to water, liquid ammonia also undergoes auto-ionization, , where the rate constant is k = 1.9 × 10-38.

References

  1. Robert Klement; Otto Koch (1954). "Phosphoroxy‐triamid und Phosphorthio‐triamid". Chemische Berichte. 87 (3): 333–340. doi:10.1002/cber.19540870308.
  2. IUPAC , Compendium of Chemical Terminology , 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006) " phosphoramides ". doi : 10.1351/goldbook.A00484