Phosphoryl group

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A phosphoryl group is a trivalent >P(=O)− group, consisting of a phosphorus atom (symbol P) and an oxygen atom (symbol O), where the three free valencies are on the phosphorus atom. While commonly depicted as possessing a double bond (P=O) the bonding is in fact non-classical. [1]

Despite that, the meaning of the term "phosphoryl" varies, depending on the branch of scientific discipline. In biology, biochemistry and biomedicine branches, the term "phosphoryl" refers to groups consisting of phosphorus atom attached to three oxygen atoms, with the simplified chemical formula −PO3 (there are several groups called "phosphoryl" in those branches, with the chemical formulas −P(=O)(−O)2, −P(=O)(−O)(−OH), −P(=O)(−OH)2, −P(=O)(−O)−O−, −P(=O)(−OH)−O− and −P(=O)(−O−)2). In the branches mentioned above, the "phosphoryl" and phosphate groups are sometimes abbreviated by the letter "P", or represented by a symbol of encircled letter "P". [2] [3] "Phosphoryl" groups are covalently bonded by a single bond to an organic molecule, phosphate group(s) or another "phosphoryl" group(s), and those groups are sp3 hybridized at the phosphorus atom. [4] The term "phosphoryl" in the mentioned branches is usually used in the description of catalytic mechanisms in living organisms. The "phosphoryl" group plays a central role in phosphorylation. In biochemical reactions involving phosphate groups (e.g. adenosine triphosphate), a "phosphoryl" group is usually transferred between the substrates by the "phosphoryl transfer reactions" (see phosphorylation). Examples of molecules containing those groups in biology, biochemistry and biomedicine are adenosine monophosphate (AMP), adenosine diphosphate (ADP), adenosine triphosphate (ATP), phosphocreatine (PCr) and DNA.

Contrary to biology, biochemistry and biomedicine branches, in organic and inorganic chemistry branches, and in the branche of chemical nomenclature (see IUPAC), the correct name for the −P(=O)(−O)2 group is not "phosphoryl", but phosphonato, and the correct name for the −P(=O)(−OH)2 group is phosphono, and the term phosphoryl correctly refers to the trivalent >P(=O)− group. [2] [5] Example of molecules containing that trivalent phosphoryl group are phosphoryl chloride (O=P(−Cl)3), methylphosphonyl dichloride (O=P(−CH3)(−Cl)2) and phosphoramide (O=P(−NH2)3).

A phosphoryl group should not be confused with a phosphate group.

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<span class="mw-page-title-main">Phosphorylation</span> Chemical process of introducing a phosphate

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<span class="mw-page-title-main">Pyrophosphate</span> Class of chemical compounds

In chemistry, pyrophosphates are phosphorus oxyanions that contain two phosphorus atoms in a P–O–P linkage. A number of pyrophosphate salts exist, such as disodium pyrophosphate (Na2H2P2O7) and tetrasodium pyrophosphate (Na4P2O7), among others. Often pyrophosphates are called diphosphates. The parent pyrophosphates are derived from partial or complete neutralization of pyrophosphoric acid. The pyrophosphate bond is also sometimes referred to as a phosphoanhydride bond, a naming convention which emphasizes the loss of water that occurs when two phosphates form a new P–O–P bond, and which mirrors the nomenclature for anhydrides of carboxylic acids. Pyrophosphates are found in ATP and other nucleotide triphosphates, which are important in biochemistry. The term pyrophosphate is also the name of esters formed by the condensation of a phosphorylated biological compound with inorganic phosphate, as for dimethylallyl pyrophosphate. This bond is also referred to as a high-energy phosphate bond.

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

Phosphorous acid (or phosphonic acid) is the compound described by the formula H3PO3. This acid is diprotic (readily ionizes two protons), not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids.

<span class="mw-page-title-main">Phosphoric acids and phosphates</span>

A phosphoric acid, in the general sense, is a phosphorus oxoacid in which each phosphorus (P) atom is in the oxidation state +5, and is bonded to four oxygen (O) atoms, one of them through a double bond, arranged as the corners of a tetrahedron. Two or more of these PO
4
tetrahedra may be connected by shared single-bonded oxygens, forming linear or branched chains, cycles, or more complex structures. The single-bonded oxygen atoms that are not shared are completed with acidic hydrogen atoms. The general formula of a phosphoric acid is H
n+2−2x
P
n
O
3n+1−x
, where n is the number of phosphorus atoms and x is the number of fundamental cycles in the molecule's structure, between 0 and (n+2)/2.

Phosphorus oxoacid is a generic name for any acid whose molecule consists of atoms of phosphorus, oxygen, and hydrogen. There is a potentially infinite number of such compounds. Some of them are unstable and have not been isolated, but the derived anions and organic groups are present in stable salts and esters. The most important ones—in biology, geology, industry, and chemical research—are the phosphoric acids, whose esters and salts are the phosphates.

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

Phosphoryl chloride is a colourless liquid with the formula POCl3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate.

A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC).

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

<span class="mw-page-title-main">Phosphine oxide</span> Class of chemical compounds

Phosphine oxides are phosphorus compounds with the formula OPX3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl3).

In enzymology, a nucleoside-phosphate kinase is an enzyme that catalyzes the chemical reaction

Thiophosphates (or phosphorothioates, PS) are chemical compounds and anions with the general chemical formula PS
4−x
O3−
x
(x = 0, 1, 2, or 3) and related derivatives where organic groups are attached to one or more O or S. Thiophosphates feature tetrahedral phosphorus(V) centers.

References

  1. Gilheany, Declan G. (1 July 1994). "No d Orbitals but Walsh Diagrams and Maybe Banana Bonds: Chemical Bonding in Phosphines, Phosphine Oxides, and Phosphonium Ylides". Chemical Reviews. 94 (5): 1339–1374. doi:10.1021/cr00029a008.
  2. 1 2 3 Nomenclature, Iupac-Iub Commission On Biochemical (1977). "Nomenclature of phosphorus-containing compounds of biochemical importance (Recommendations 1976)". Proceedings of the National Academy of Sciences. 74 (6): 2222–2230. Bibcode:1977PNAS...74.2222O. doi: 10.1073/pnas.74.6.2222 . PMC   432142 . PMID   16592403.
  3. "CHEM 245 - Phosphate and phosphoryl groups".
  4. "10.1: Overview of phosphates and phosphoryl transfer reactions". 2 October 2013.
  5. "Chemical Entities of Biological Interest (ChEBI)".