A phosphoryl group is a

trivalent In chemistry, the valence (US spelling) or valency (British spelling) of an atom is a measure of its combining capacity with other atoms when it forms chemical compounds or molecules. Valence is generally understood to be the number of chemica ...

group, consisting of a

phosphorus Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...

atom (symbol P) and an

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

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. Despite that, the meaning of the term "phosphoryl" varies, depending on the branch of

scientific discipline The branches of science, also referred to as sciences, scientific fields or scientific disciplines, are commonly divided into three major groups: * Formal sciences: the study of formal systems, such as those under the branches of logic and mat ...

. For example, in

biology Biology is the scientific study of life and living organisms. It is a broad natural science that encompasses a wide range of fields and unifying principles that explain the structure, function, growth, History of life, origin, evolution, and ...

biochemistry Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, a ...

and

biomedicine Biomedicine (also referred to as Western medicine, mainstream medicine or conventional medicine)

branches, the term "phosphoryl" refers to groups consisting of phosphorus atom attached to three oxygen atoms, with the simplified

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

(there are several groups called "phosphoryl" in those branches, with the chemical formulas , , , , and ). In the branches mentioned above, the "phosphoryl" and

phosphate Phosphates are the naturally occurring form of the element phosphorus. In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...

groups are sometimes abbreviated by the letter "P", or represented by a symbol of encircled letter "P". "Phosphoryl" groups are

covalently A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...

bonded by a

single bond In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of th ...

to an

organic molecule Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-cont ...

group(s) or another "phosphoryl" group(s), and those groups are sp³ hybridized at the phosphorus atom. 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 biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols: : This equation can be writ ...

. In

biochemical reaction Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, a ...

s involving phosphate groups (e.g. adenosine triphosphate), a "phosphoryl" group is usually transferred between the substrates by the "phosphoryl transfer reactions" (see

). Examples of molecules containing those groups in biology, biochemistry and biomedicine are

adenosine monophosphate Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. It is an ester of phosphoric acid and the nucleoside adenosine. As a substituent it t ...

(AMP),

adenosine diphosphate Adenosine diphosphate (ADP), also known as adenosine pyrophosphate (APP), is an important organic compound in metabolism and is essential to the flow of energy in living cells. ADP consists of three important structural components: a sugar backbon ...

(ADP),

adenosine triphosphate Adenosine triphosphate (ATP) is a nucleoside triphosphate that provides energy to drive and support many processes in living cell (biology), cells, such as muscle contraction, nerve impulse propagation, and chemical synthesis. Found in all known ...

(ATP),

phosphocreatine Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylation, phosphorylated form of creatine that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recyc ...

(PCr) and

DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

. Contrary to

and

biomedicine Biomedicine (also referred to as Western medicine, mainstream medicine or conventional medicine)

branches, in

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

and

inorganic chemistry Inorganic chemistry deals with chemical synthesis, synthesis and behavior of inorganic compound, inorganic and organometallic chemistry, organometallic compounds. This field covers chemical compounds that are not carbon-based, which are the subj ...

branches, and in the branch of

chemical nomenclature Chemical nomenclature is a set of rules to generate systematic name#In chemistry, systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Appli ...

(see

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

), the correct name for the group is not "phosphoryl", but phosphonato, and the correct name for the group is phosphono, and the term phosphoryl correctly refers to the trivalent >P(=O)− group. Example of molecules containing that trivalent phosphoryl group are

phosphoryl chloride Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosp ...

(),

methylphosphonyl dichloride Methylphosphonyl dichloride (DC) or dichloro is an organophosphorus compound. It has commercial application in oligonucleotide synthesis, but is most notable as being a precursor to several chemical weapons agents. It is a white crystalline solid ...

() and

phosphoramide Phosphoramide is a chemical compound with the molecular formula . 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 s ...

(). A phosphoryl group should not be confused with a

group.

References

{{reflist Phosphorus–oxygen compounds Functional groups