Home Discussion Topics Dictionary Almanac

Signup Login

Functional group

Overview

In organic chemistry

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

, functional groups are specific groups of atom

Atom

The atom is a basic unit of matter that consists of a dense central nucleus surrounded by a cloud of negatively charged electrons. The atomic nucleus contains a mix of positively charged protons and electrically neutral neutrons...

s within molecule

Molecule

A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...

s that are responsible for the characteristic chemical reaction

Chemical reaction

A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...

Discussion

Ask a question about 'Functional group'

Start a new discussion about 'Functional group'

Answer questions from other users

Full Discussion Forum

Unanswered Questions

In IUPAC system, What is the prefix for ester, -COOR: Alkoxycarbonyl or alkyloxycarbonyl?

Why isothiocyants can't form dimers?

Recent Discussions

Is there any relationship to carbon chain length and the functional group?

Encyclopedia

In organic chemistry

Organic chemistry

, functional groups are specific groups of atom

Atom

s within molecule

Molecule

A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...

s that are responsible for the characteristic chemical reaction

Chemical reaction

s of those molecules. The same functional group will undergo the same or similar chemical reaction(s) regardless of the size of the molecule it is a part of. However, its relative reactivity can be modified by nearby functional groups.

The word moiety (ˈmɔɪəti) is often used synonymously to "functional group," but, according to the IUPAC

International Union of Pure and Applied Chemistry

The International Union of Pure and Applied Chemistry is an international federation of National Adhering Organizations that represents chemists in individual countries. It is a member of the International Council for Science . The international headquarters of IUPAC is located in Zürich,...

definition, a moiety is a part of a molecule that may include either whole functional groups or a parts of functional groups as substructures. For example, an ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

(RCOOR') has an ester functional group (COOR) and is composed of an alkoxy moiety (-OR') and an acyl moiety (RCO-), or, equivalently, it may be divided into carboxylate (RCOO-) and alkyl (-R') moieties. Each moiety may contain additional functional groups, for example, methyl para-hydroxybenzoate contains a phenol

Phenol

Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

functional group within the acyl moiety.

Combining the names of functional groups with the names of the parent alkane

Alkane

Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...

s generates a powerful systematic nomenclature

Systematic name

A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection...

for naming organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

s.

The atoms of functional groups are linked to each other and to the rest of the molecule by covalent bond

Covalent bond

A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. The stable balance of attractive and repulsive forces between atoms when they share electrons is known as covalent bonding....

s. When the group of covalently bound atoms bears a net charge

Ion

An ion is an atom or molecule in which the total number of electrons is not equal to the total number of protons, giving it a net positive or negative electrical charge. The name was given by physicist Michael Faraday for the substances that allow a current to pass between electrodes in a...

, the group is referred to more properly as a polyatomic ion

Polyatomic ion

A polyatomic ion, also known as a molecular ion, is a charged species composed of two or more atoms covalently bonded or of a metal complex that can be considered as acting as a single unit in the context of acid and base chemistry or in the formation of salts. The prefix "poly-" means "many," in...

or a complex ion. Any subgroup of atoms of a compound also may be called a radical, and if a covalent bond is broken homolytically

Homolysis

In general it means breakdown to equal pieces There are separate meanings for the word in chemistry and biology.-Homolysis in chemistry:...

, the resulting fragment radicals are referred as free radicals.

The first carbon

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

atom after the carbon that attaches to the functional group is called the alpha carbon

Alpha carbon

The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....

; the second, beta carbon, the third, gamma carbon, etc. If there is another functional group at a carbon, it may be named with the Greek letter, e.g., the gamma-amine in gamma-aminobutanoic acid is on the third carbon of the carbon chain attached to the carboxylic acid group.

Synthetic chemistry

Organic reactions are facilitated and controlled by the functional groups of the reactants. In general, alkyls are unreactive and difficult to get to react selectively at the desired positions, with few exceptions. In contrast, unsaturated carbon functional groups, and carbon-oxygen and carbon-nitrogen functional groups have a more diverse array of reactions that are also selective. It may be necessary to create a functional group in the molecule to make it react. For example, to synthesize iso-octane (the 8-carbon ideal gasoline

Gasoline

Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...

) from the unfunctionalized alkane isobutane (a 4-carbon gas), isobutane is first dehydrogenated

Dehydrogenation

Dehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....

into isobutene. This contains the alkene

Alkene

In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

functional group and can now dimerize with another isobutene to give iso-octene, which is then catalytically hydrogenated

Hydrogenation

Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...

to iso-octane using pressured hydrogen

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

gas.

Crystallography

The International Union of Crystallography

International Union of Crystallography

The International Union of Crystallography is a member of the International Council for Science and exists to serve the world community of crystallographers....

in its Crystallographic Information File

Crystallographic Information File

Crystallographic Information File is a standard text file format for representing crystallographic information, promulgated by the International Union of Crystallography . CIF was developed by the IUCr Working Party on Crystallographic Information in an effort sponsored by the IUCr Commission on...

dictionary defines "moiety" to represent discrete non-bonded components. Thus, would contain 3 moieties (2 Na⁺ and one SO₄^2-). The dictionary defines "chemical formula moiety": "Formula with each discrete bonded residue or ion shown as a separate moiety".

Functionalization

Functionalization is the addition of functional groups onto the surface of a material by chemical synthesis methods. The functional group added can be subjected to ordinary synthesis methods to attach virtually any kind of organic compound onto the surface.

Functionalization is employed for surface modification of industrial materials in order to achieve desired surface properties such as water repellent coatings for automobile windshields and non-biofouling, hydrophilic coatings for contact lenses. In addition, functional groups are used to covalently link functional molecules to the surface of chemical and biochemical devices such as microarrays and microelectromechanical systems

Microelectromechanical systems

Microelectromechanical systems is the technology of very small mechanical devices driven by electricity; it merges at the nano-scale into nanoelectromechanical systems and nanotechnology...

.

Catalysts can be attached to a material that has been functionalized. For example, silica is functionalized with an alkyl silicone, wherein the alkyl contains an amine functional group. A ligand such as an EDTA

EDTA

Ethylenediaminetetraacetic acid, widely abbreviated as EDTA , is a polyamino carboxylic acid and a colourless, water-soluble solid. Its conjugate base is named ethylenediaminetetraacetate. It is widely used to dissolve limescale. Its usefulness arises because of its role as a hexadentate ligand...

fragment is synthesized onto the amine, and a metal cation is complexed into the EDTA fragment. The EDTA is not adsorbed onto the surface, but connected by a permanent chemical bond.

Functional groups are also used to covalently link molecules such as fluorescent dyes, nanoparticles, proteins, DNA, and other compounds of interest for a variety of applications such as sensing and basic chemical research.

Table of common functional groups

The following is a list of common functional groups. In the formulas, the symbols R and R' usually denote an attached hydrogen, or a hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....

side chain

Side chain

In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called "main chain" or backbone. The placeholder R is often used as a generic placeholder for alkyl group side chains in chemical structure diagrams. To indicate other non-carbon...

of any length, but may sometimes refer to any group of atoms.

Hydrocarbons

Functional groups, called hydrocarbyls, that contain only carbon and hydrogen, but vary in the number and order of π bonds. Each one differs in type (and scope) of reactivity.

Chemical class	Group	Formula	Prefix	Suffix	Example
Alkane Alkane Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...	Alkyl Alkane Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...	RH	alkyl-	-ane	Ethane Ethane Ethane is a chemical compound with chemical formula C2H6. It is the only two-carbon alkane that is an aliphatic hydrocarbon. At standard temperature and pressure, ethane is a colorless, odorless gas....
Alkene Alkene In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...	Alkenyl Alkene In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...	R₂C=CR₂	alkenyl-	-ene	Ethylene Ethylene Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone... (Ethene)
Alkyne Alkyne Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature...	Alkynyl Alkyne Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature...	RC≡CR'	alkynyl-	-yne	Acetylene Acetylene Acetylene is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because... (Ethyne)
Benzene derivative Benzene Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....	Phenyl	RC₆H₅ RPh	phenyl-	-benzene	Cumene Cumene Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C... (2-phenylpropane)
Toluene derivative Toluene Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...	Benzyl Benzyl In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-. Benzyl features a benzene ring attached to a CH2 group.-Nomenclature:...	RCH₂C₆H₅ RBn	benzyl-	1-(substituent)toluene	Benzyl bromide Benzyl bromide Benzyl bromide, or α-bromotoluene, is an organic compound consisting of a benzene ring substituted with a bromomethyl group. It can be prepared by the bromination of toluene at room temperature in air, using manganese oxide as a heterogeneous catalyst... (α-Bromotoluene)

There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc.

Hydrocarbons may form charged structures: positively charged carbocation

Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer valence shell instead of the eight valence electrons that ensures maximum stability . Therefore carbocations are often reactive,...

s or negative carbanion

Carbanion

A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. The carbanion exists in a trigonal pyramidal geometry. Formally a carbanion is the conjugate base of a carbon acid.where B...

s. Carbocations are often named -um. Examples are tropylium and triphenylmethyl cations and the cyclopentadienyl

Cyclopentadienyl

In organic chemistry, cyclopentadienyl is a cyclic group of atoms with the formula C5H5. Cyclopentadienyl are closely related to cyclopentadiene. Cyclopentadienyl have five carbon atoms bonded together in a pentagonal planar ring, all five of which are bonded to individual hydrogen atoms...

anion.

Groups containing halogens

Haloalkanes are a class of molecule that is defined by a carbon-halogen

Halogen

The halogens or halogen elements are a series of nonmetal elements from Group 17 IUPAC Style of the periodic table, comprising fluorine , chlorine , bromine , iodine , and astatine...

bond. This bond can be relatively weak (in the case of an iodoalkane) or quite stable (as in the case of a fluoroalkane). In general, with the exception of fluorinated compounds, haloalkanes readily undergo nucleophilic substitution

Nucleophilic substitution

In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms called the leaving group; the positive or partially positive...

reactions or elimination reaction

Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism...

s. The substitution on the carbon, the acidity of an adjacent proton, the solvent conditions, etc. all can influence the outcome of the reactivity.

Chemical class	Group	Formula	Prefix	Suffix	Example
haloalkane Haloalkane The haloalkanes are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and...	halo Halogen The halogens or halogen elements are a series of nonmetal elements from Group 17 IUPAC Style of the periodic table, comprising fluorine , chlorine , bromine , iodine , and astatine...	RX	halo-	alkyl halide	Chloroethane Chloroethane Chloroethane or monochloroethane, commonly known by its old name ethyl chloride, is a chemical compound with chemical formula , once widely used in producing tetraethyllead, a gasoline additive... (Ethyl chloride)
fluoroalkane	fluoro Fluorine Fluorine is the chemical element with atomic number 9, represented by the symbol F. It is the lightest element of the halogen column of the periodic table and has a single stable isotope, fluorine-19. At standard pressure and temperature, fluorine is a pale yellow gas composed of diatomic...	RF	fluoro-	alkyl fluoride	Fluoromethane Fluoromethane Fluoromethane, also known as methyl fluoride, Freon 41, Halocarbon-41 and HFC-41, is a non-toxic, liquefiable, and flammable gas at standard temperature and pressure. It is made of carbon, hydrogen, and fluorine. The name stems from the fact that it is methane plus fluorine, minus a hydrogen... (Methyl fluoride)
chloroalkane	chloro Chlorine Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...	RCl	chloro-	alkyl chloride	Chloromethane Chloromethane Chloromethane, also called methyl chloride, R-40 or HCC 40, is a chemical compound of the group of organic compounds called haloalkanes. It was once widely used as a refrigerant. It is a colorless extremely flammable gas with a minorly sweet odor, which is, however, detected at possibly toxic levels... (Methyl chloride)
bromoalkane	bromo Bromine Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...	RBr	bromo-	alkyl bromide	Bromomethane (Methyl bromide)
iodoalkane	iodo Iodine Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....	RI	iodo-	alkyl iodide	Iodomethane Iodomethane Methyl iodide, also called iodomethane, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally... (Methyl iodide)

Groups containing oxygen

Compounds that contain C-O bonds each possess differing reactivity based upon the location and hybridization

Orbital hybridisation

In chemistry, hybridisation is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. Hybridised orbitals are very useful in the explanation of the shape of molecular orbitals for molecules. It is an integral part...

of the C-O bond, owing to the electron-withdrawing effect of sp hybridized oxygen (carbonyl groups) and the donating effects of sp² hybridized oxygen (alcohol groups).

Chemical class	Group	Formula	Prefix	Suffix	Example
Alcohol Alcohol In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....	Hydroxyl Hydroxyl A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...	ROH	hydroxy-	-ol	Methanol Methanol Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
Ketone Ketone In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...	Carbonyl Carbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....	RCOR'	-oyl- (-COR') or oxo- (=O)	-one	Butanone Butanone Butanone, also known as methyl ethyl ketone or MEK, is an organic compound with the formula CH3CCH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of butterscotch and acetone. It is produced industrially on a large scale, and also occurs in trace amounts in nature... (Methyl ethyl ketone)
Aldehyde Aldehyde An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....	Aldehyde Aldehyde An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....	RCHO	formyl- (-COH) or oxo- (=O)	-al	Ethanal (Acetaldehyde Acetaldehyde Acetaldehyde is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part... )
Acyl halide Acyl halide An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group....	Haloformyl	RCOX	carbonofluoridoyl- carbonochloridoyl- carbonobromidoyl- carbonoiodidoyl-	-oyl halide	Acetyl chloride Acetyl chloride Acetyl chloride, CH3COCl, also known as ethanoyl chloride or acyl chloride, is an acid chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless liquid. Acetyl chloride does not exist in nature, because contact with water would hydrolyze... (Ethanoyl chloride)
Carbonate Carbonate ester A carbonate ester is a functional group in organic chemistry consisting of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R1OOR2 and they are related to esters R1OR and ethers R1OR2 and also to the inorganic carbonates.Carbonate esters are used as...	Carbonate ester Carbonate ester A carbonate ester is a functional group in organic chemistry consisting of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R1OOR2 and they are related to esters R1OR and ethers R1OR2 and also to the inorganic carbonates.Carbonate esters are used as...	ROCOOR	(alkoxycarbonyl)oxy-	alkyl carbonate	Triphosgene Triphosgene Triphosgene is a chemical compound that is used as a safer substitute for phosgene, because at room temperature it is a solid crystal, as opposed to phosgene which is a gas. Triphosgene crystals decompose at around 130 °C, although, the decomposition temperature of impure samples can be much lower... (Di(trichloromethyl) carbonate)
Carboxylate Carboxylic acid Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...	Carboxylate	RCOO⁻	carboxy-	-oate	Sodium acetate Sodium acetate Sodium acetate, CH3COONa, also abbreviated NaOAc, also sodium ethanoate, is the sodium salt of acetic acid. This colourless salt has a wide range of uses.-Industrial:... (Sodium ethanoate)
Carboxylic acid Carboxylic acid Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...	Carboxyl	RCOOH	carboxy-	-oic acid	Acetic acid Acetic acid Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell... (Ethanoic acid)
Ester Ester Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...	Ester Ester Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...	RCOOR'	alkanoyloxy- or alkoxycarbonyl	alkyl alkanoate	Ethyl butyrate Ethyl butyrate Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COOCH2CH3. It is soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple.-Uses:... (Ethyl butanoate)
Hydroperoxide Organic peroxide Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...	Hydroperoxy Organic peroxide Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...	ROOH	hydroperoxy-	alkyl hydroperoxide	Methyl ethyl ketone peroxide Methyl ethyl ketone peroxide Methyl ethyl ketone peroxide is an organic peroxide, a high explosive similar to acetone peroxide. MEKP is a colorless, oily liquid whereas acetone peroxide is a white powder at STP; MEKP is slightly less sensitive to shock and temperature, and more stable in storage.Dilute solutions of 30 to 60%...
Peroxide Organic peroxide Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...	Peroxy Organic peroxide Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...	ROOR	peroxy-	alkyl peroxide	Di-tert-butyl peroxide
Ether Ether Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...	Ether Ether Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...	ROR'	alkoxy-	alkyl ether	Diethyl ether Diethyl ether Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor... (Ethoxyethane)
Hemiacetal Hemiacetal Hemiacetals and hemiketals are compounds that are derived from aldehydes and ketones respectively. The Greek word hèmi means half...	Hemiacetal Hemiacetal Hemiacetals and hemiketals are compounds that are derived from aldehydes and ketones respectively. The Greek word hèmi means half...	RCH(OR')(OH)	alkoxy -ol	-al alkyl hemiacetal
Hemiketal	Hemiketal	RC(ORʺ)(OH)R'	alkoxy -ol	-one alkyl hemiketal
Acetal Acetal An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...	Acetal Acetal An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals...	RCH(OR')(OR")	dialkoxy-	-al dialkyl acetal
Ketal (or Acetal Acetal An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals... )	Ketal (or Acetal Acetal An acetal is a molecule with two single-bonded oxygen atoms attached to the same carbon atom.Traditional usages distinguish ketals from acetals... )		dialkoxy-	-one dialkyl ketal
Orthoester Orthoester In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC3. The name can also refer to any organic compound that contains this functional group. An example of an orthoester is ethyl orthoacetate, CH3C3,...	Orthoester Orthoester In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC3. The name can also refer to any organic compound that contains this functional group. An example of an orthoester is ethyl orthoacetate, CH3C3,...		trialkoxy-
Orthocarbonate ester	Orthocarbonate ester		tetralkoxy-	tetraalkyl orthocarbonate

Groups containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amide

Amide

In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...

Chemical class	Group	Formula	Prefix	Suffix	Example
Amide Amide In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...	Carboxamide Carboxamide In organic chemistry carboxamides are functional groups with the general structure R-CO-NH2 with R as an organic substituent.Two amino acids, asparagine and glutamine, have a carboxamide group in them....	RCONR₂	carboxamido- or carbamoyl-	-amide	Acetamide Acetamide Acetamide is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent... (Ethanamide)
Amine Amine Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are 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,... s	Primary amine Amine Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are 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,...	RNH₂	amino-	-amine	Methylamine Methylamine Methylamine is the organic compound with a formula of CH3NH2. This colourless gas is a derivative of ammonia, but with one H atom replaced by a methyl group. It is the simplest primary amine. It is sold as a solution in methanol, ethanol, THF, and water, or as the anhydrous gas in pressurized... (Methanamine)
	Secondary amine Amine Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are 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,...	R₂NH	amino-	-amine	Dimethylamine Dimethylamine Dimethylamine is an organic compound with the formula 2NH. This secondary amine is a colorless, flammable liquified gas with an ammonia-like odor. Dimethylamine is generally encountered as a solution in water at concentrations up to around 40%...
	Tertiary amine Amine Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are 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,...	R₃N	amino-	-amine	Trimethylamine Trimethylamine Trimethylamine is an organic compound with the formula N3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations...
	4° ammonium ion Quaternary ammonium cation Quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure NR4+, R being an alkyl group or an aryl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged,...	R₄N⁺	ammonio-	-ammonium	Choline Choline Choline is a water-soluble essential nutrient. It is usually grouped within the B-complex vitamins. Choline generally refers to the various quaternary ammonium salts containing the N,N,N-trimethylethanolammonium cation....
Imine Imine An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...	Primary ketimine Imine An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...	RC(=NH)R'	imino-	-imine
	Secondary ketimine Imine An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...	RC(=NR)R'	imino-	-imine
	Primary aldimine Imine An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...	RC(=NH)H	imino-	-imine
	Secondary aldimine Imine An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...	RC(=NR')H	imino-	-imine
Imide Imide In organic chemistry, an imide is a functional group consisting of two carbonyl groups bound to nitrogen. These compounds are structurally related to acid anhydrides. The relationship between esters and amides and between imides and anhydrides is analogous, the amine-derived groups are less reactive...	Imide Imide In organic chemistry, an imide is a functional group consisting of two carbonyl groups bound to nitrogen. These compounds are structurally related to acid anhydrides. The relationship between esters and amides and between imides and anhydrides is analogous, the amine-derived groups are less reactive...	(RCO)₂NR'	imido-	-imide
Azide Azide Azide is the anion with the formula N3−. It is the conjugate base of hydrazoic acid. N3− is a linear anion that is isoelectronic with CO2 and N2O. Per valence bond theory, azide can be described by several resonance structures, an important one being N−=N+=N−...	Azide Azide Azide is the anion with the formula N3−. It is the conjugate base of hydrazoic acid. N3− is a linear anion that is isoelectronic with CO2 and N2O. Per valence bond theory, azide can be described by several resonance structures, an important one being N−=N+=N−...	RN₃	azido-	alkyl azide	Phenyl azide Phenyl azide Phenylazide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It has a pungent odor. The structure consists of a linear azide substituent bound to a phenyl group... (Azidobenzene)
Azo compound Azo compound Azo compounds are compounds bearing the functional group R-N=N-R', in which R and R' can be either aryl or alkyl. IUPAC defines azo compounds as: "Derivatives of diazene , HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene." The more...	Azo (Diimide) Azo compound Azo compounds are compounds bearing the functional group R-N=N-R', in which R and R' can be either aryl or alkyl. IUPAC defines azo compounds as: "Derivatives of diazene , HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene." The more...	RN₂R'	azo-	-diazene	Methyl orange Methyl orange Methyl orange is a pH indicator frequently used in titrations.It is often used in titrations because of its clear and distinct colour change. Because it changes colour at the pH of a mid-strength acid, it is usually used in titrations for acids... (p-dimethylamino-azobenzenesulfonic acid)
Cyanate Cyanate The cyanate ion is an anion with the chemical formula written as [OCN]− or [NCO]−. In aqueous solution it acts as a base, forming isocyanic acid, HNCO. The cyanate ion is an ambidentate ligand, forming complexes with a metal ion in which either the nitrogen or oxygen atom may be the electron-pair... s	Cyanate Cyanate The cyanate ion is an anion with the chemical formula written as [OCN]− or [NCO]−. In aqueous solution it acts as a base, forming isocyanic acid, HNCO. The cyanate ion is an ambidentate ligand, forming complexes with a metal ion in which either the nitrogen or oxygen atom may be the electron-pair...	ROCN	cyanato-	alkyl cyanate	Methyl cyanate
	Isocyanate Isocyanate Isocyanate is the functional group of elements –N=C=O , not to be confused with the cyanate functional group which is arranged as –O–C≡N or with isocyanide, R-N≡C. Any organic compound which contains an isocyanate group may also be referred to in brief as an isocyanate. An isocyanate may have more...	RNCO	isocyanato-	alkyl isocyanate	Methyl isocyanate Methyl isocyanate Methyl isocyanate is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane, methyl carbylamine, and MIC. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides . It has also been used in the production of rubbers and adhesives...
Nitrate Nitrate The nitrate ion is a polyatomic ion with the molecular formula NO and a molecular mass of 62.0049 g/mol. It is the conjugate base of nitric acid, consisting of one central nitrogen atom surrounded by three identically-bonded oxygen atoms in a trigonal planar arrangement. The nitrate ion carries a...	Nitrate Nitrate The nitrate ion is a polyatomic ion with the molecular formula NO and a molecular mass of 62.0049 g/mol. It is the conjugate base of nitric acid, consisting of one central nitrogen atom surrounded by three identically-bonded oxygen atoms in a trigonal planar arrangement. The nitrate ion carries a...	RONO₂	nitrooxy-, nitroxy-	alkyl nitrate	Amyl nitrate Amyl nitrate Amyl nitrate is the chemical compound with the formula CH34ONO2. This molecule consists of the 5-carbon amyl group attached to a nitrate functional group. It is the ester of amyl alcohol and nitric acid.-Applications:... (1-nitrooxypentane)
Nitrile Nitrile A nitrile is any organic compound that has a -C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, one example being super glue .Inorganic compounds containing the -C≡N group are not called...	Nitrile Nitrile A nitrile is any organic compound that has a -C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, one example being super glue .Inorganic compounds containing the -C≡N group are not called...	RCN	cyano-	alkanenitrile alkyl cyanide	Benzonitrile Benzonitrile Benzonitrile is the chemical compound with the formula C6H5CN, abbreviated PhCN. This aromatic organic compound is colourless, with a sweet almond odour. It is prepared by the dehydration of benzamide, or by the reaction of sodium cyanide with bromobenzene.... (Phenyl cyanide)
	Isonitrile	RNC	isocyano-	alkaneisonitrile alkyl isocyanide	Methyl isocyanide Methyl isocyanide Methyl isocyanide or Isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is structurally similar to the isomeric methyl cyanide , but its reactivity is very different...
Nitrite Nitrite The nitrite ion has the chemical formula NO2−. The anion is symmetric with equal N-O bond lengths and a O-N-O bond angle of ca. 120°. On protonation the unstable weak acid nitrous acid is produced. Nitrite can be oxidised or reduced, with product somewhat dependent on the oxidizing/reducing agent...	Nitrosooxy Nitrite The nitrite ion has the chemical formula NO2−. The anion is symmetric with equal N-O bond lengths and a O-N-O bond angle of ca. 120°. On protonation the unstable weak acid nitrous acid is produced. Nitrite can be oxidised or reduced, with product somewhat dependent on the oxidizing/reducing agent...	RONO	nitrosooxy-	alkyl nitrite	Isoamyl nitrite (3-methyl-1-nitrosooxybutane)
Nitro compound Nitro compound Nitro compounds are organic compounds that contain one or more nitro functional groups . They are often highly explosive, especially when the compound contains more than one nitro group and is impure. The nitro group is one of the most common explosophores used globally...	Nitro	RNO₂	nitro-		Nitromethane Nitromethane Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...
Nitroso compound Nitroso Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds are a class of organic compounds containing the nitroso functional group, R−N=O....	Nitroso Nitroso Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds are a class of organic compounds containing the nitroso functional group, R−N=O....	RNO	nitroso-		Nitrosobenzene Nitrosobenzene Nitrosobenzene is the organic compound with the formula C6H5NO. The compound can be viewed as hybrid of singlet O2 and azobenzene. This diamagnetic species exists in equilibrium with its dimer.-Preparation:...
Pyridine derivative Pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...	Pyridyl Pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...	RC₅H₄N	4-pyridyl (pyridin-4-yl) 3-pyridyl (pyridin-3-yl) 2-pyridyl (pyridin-2-yl)	-pyridine	Nicotine Nicotine Nicotine is an alkaloid found in the nightshade family of plants that constitutes approximately 0.6–3.0% of the dry weight of tobacco, with biosynthesis taking place in the roots and accumulation occurring in the leaves...

Groups containing sulphur

Compounds that contain sulfur exhibit unique chemistry due to their ability to form more bonds than oxygen, their lighter analogue on the periodic table. Substitutive nomenclature (marked as prefix in table) is preferred over functional class nomenclature (marked as suffix in table) for sulfides, disulfides, sulfoxides and sulfones.

Chemical class	Group	Formula	Prefix	Suffix	Example
Thiol Thiol In organic chemistry, a thiol is an organosulfur compound that contains a carbon-bonded sulfhydryl group...	Sulfhydryl Thiol In organic chemistry, a thiol is an organosulfur compound that contains a carbon-bonded sulfhydryl group...	RSH	sulfanyl- (-SH)	-thiol	Ethanethiol Ethanethiol Ethanethiol is an organic compound with the formula CH3CH2SH. It consists of an ethyl group, CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with S instead of O. The presence of S leads to many different properties, most notably the infamous odour of EtSH...
Sulfide Sulfide A sulfide is an anion of sulfur in its lowest oxidation state of 2-. Sulfide is also a slightly archaic term for thioethers, a common type of organosulfur compound that are well known for their bad odors.- Properties :... (Thioether Thioether A thioether is a functional group in organosulfur chemistry with the connectivity C-S-C as shown on right. Like many other sulfur-containing compounds, volatile thioethers have foul odors. A thioether is similar to an ether except that it contains a sulfur atom in place of the oxygen... )	Sulfide Sulfide A sulfide is an anion of sulfur in its lowest oxidation state of 2-. Sulfide is also a slightly archaic term for thioethers, a common type of organosulfur compound that are well known for their bad odors.- Properties :...	RSR'	substituent sulfanyl- (-SR')	di(substituent) sulfide	(Methylsulfanyl)methane (prefix) or Dimethyl sulfide Dimethyl sulfide Dimethyl sulfide or methylthiomethane is an organosulfur compound with the formula 2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize,... (suffix)
Disulfide Disulfide bond In chemistry, a disulfide bond is a covalent bond, usually derived by the coupling of two thiol groups. The linkage is also called an SS-bond or disulfide bridge. The overall connectivity is therefore R-S-S-R. The terminology is widely used in biochemistry...	Disulfide Disulfide In chemistry, a disulfide usually refers to the structural unit composed of a linked pair of sulfur atoms. Disulfide usually refer to a chemical compound that contains a disulfide bond, such as diphenyl disulfide, C6H5S-SC6H5....	RSSR'	substituent disulfanyl- (-SSR')	di(substituent) disulfide	(Methyldisulfanyl)methane (prefix) or Dimethyl disulfide Dimethyl disulfide Dimethyl disulfide is an organic chemical compound with the molecular formula CH3SSCH3 which is the simplest disulfide. It is a flammable liquid with an unpleasant odor.DMDS can be produced by the reaction of methanethiol with sulfur:-Uses:... (suffix)
Sulfoxide Sulfoxide A sulfoxide is a chemical compound containing a sulfinyl functional group attached to two carbon atoms. Sulfoxides can be considered as oxidized sulfides...	Sulfinyl Sulfoxide A sulfoxide is a chemical compound containing a sulfinyl functional group attached to two carbon atoms. Sulfoxides can be considered as oxidized sulfides...	RSOR'	-sulfinyl- (-SOR')	di(substituent) sulfoxide	(Methanesulfinyl)methane (prefix) or Dimethyl sulfoxide Dimethyl sulfoxide Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water... (suffix)
Sulfone Sulfone A sulfone is a chemical compound containing a sulfonyl functional group attached to two carbon atoms. The central hexavalent sulfur atom is double bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.-IUPAC name and...	Sulfonyl Sulfone A sulfone is a chemical compound containing a sulfonyl functional group attached to two carbon atoms. The central hexavalent sulfur atom is double bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.-IUPAC name and...	RSO₂R'	-sulfonyl- (-SO₂R')	di(substituent) sulfone	(Methanesulfonyl)methane (prefix) or Dimethyl sulfone (suffix)
Sulfinic acid	Sulfino	RSO₂H	sulfino- (-SO₂H)	-sulfinic acid	2-Aminoethanesulfinic acid
Sulfonic acid	Sulfo	RSO₃H	sulfo- (-SO₃H)	-sulfonic acid	Benzenesulfonic acid Benzenesulfonic acid Benzenesulfonic acid is an organosulfur compound with the formula C6H5SO3H. It is the simplest aromatic sulfonic acid. It forms colorless deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in carbon disulfide and diethyl...
Thiocyanate Thiocyanate Thiocyanate is the anion [SCN]−. It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Organic compounds containing the functional group SCN are also called thiocyanates...	Thiocyanate Thiocyanate Thiocyanate is the anion [SCN]−. It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Organic compounds containing the functional group SCN are also called thiocyanates...	RSCN	thiocyanato- (-SCN)	substituent thiocyanate	Phenyl thiocyanate
	Isothiocyanate Isothiocyanate Isothiocyanate is the chemical group –N=C=S, formed by substituting sulfur for oxygen in the isocyanate group. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. These natural isothiocyanates, such as allyl isothiocyanate, are also...	RNCS	isothiocyanato- (-NCS)	substituent isothiocyanate	Allyl isothiocyanate Allyl isothiocyanate Allyl isothiocyanate is the organosulfur compound with the formula CH2CHCH2NCS. This colorless oil is responsible for the pungent taste of mustard, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC is mediated through the TRPA1 and TRPV1 ion channels...
Thione	Carbonothioyl	RCSR'	-thioyl- (-CSR') or sulfanylidene- (=S)	-thione	Diphenylmethanethione (Thiobenzophenone Thiobenzophenone Thiobenzophenone is an organosulfur compound with the formula 2CS. It is the prototypical thioketone. Unlike other thioketones that tend to dimerize to form rings and polymers, thiobenzophenone is quite stable, although it photoxidizes in air to form benzophenone and sulfur... )
Thial Thial A thial or thioaldehyde is a functional group in organic chemistry which is similar to an aldehyde, RCH, in which a sulfur atom replaces the oxygen atom of the aldehyde . Thioaldehydes are even more reactive than the thioketones...	Carbonothioyl	RCSH	methanethioyl- (-CSH) or sulfanylidene- (=S)	-thial

Groups containing phosphorus

Compounds that contain phosphorus exhibit unique chemistry due to their ability to form more bonds than nitrogen, their lighter analogues on the periodic table.

Chemical class	Group	Formula	Prefix	Suffix	Example
Phosphine Phosphine Phosphine is the compound with the chemical formula PH3. It is a colorless, flammable, toxic gas. Pure phosphine is odourless, but technical grade samples have a highly unpleasant odor like garlic or rotting fish, due to the presence of substituted phosphine and diphosphine... (Phosphane)	Phosphino	R₃P	phosphanyl-	-phosphane	Methylpropylphosphane
Phosphonic acid	Phosphono	RP(=O)(OH)₂	phosphono-	substituent phosphonic acid	Benzylphosphonic acid
Phosphate Phosphate A phosphate, an inorganic chemical, is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry and biogeochemistry or ecology. Inorganic phosphates are mined to obtain phosphorus for use in...	Phosphate	ROP(=O)(OH)₂	phosphonooxy- or O-phosphono- (phospho-)	substituent phosphate	Glyceraldehyde 3-phosphate Glyceraldehyde 3-phosphate Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GADP, GAP, TP, GALP or PGAL, is a chemical compound that occurs as an intermediate in several central metabolic pathways of all organisms... (suffix)
	Phosphate	ROP(=O)(OH)₂	phosphonooxy- or O-phosphono- (phospho-)	substituent phosphate	O-Phosphonocholine (prefix) (Phosphocholine Phosphocholine Phosphocholine is an intermediate in the synthesis of phosphatidylcholine in tissues. Phosphocholine is made in a reaction, catalyzed by choline kinase, that converts ATP + Choline into Phosphocholine and ADP... )
Phosphodiester	Phosphate Phosphate A phosphate, an inorganic chemical, is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry and biogeochemistry or ecology. Inorganic phosphates are mined to obtain phosphorus for use in...	HOPO(OR)₂	[(alkoxy)hydroxyphosphoryl]oxy- or O-[(alkoxy)hydroxyphosphoryl]-	di(substituent) hydrogen phosphate or phosphoric acid di(substituent) ester	DNA DNA Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
Phosphodiester		HOPO(OR)₂			O‑[(2‑Guanidinoethoxy)hydroxyphosphoryl]‑‑serine (prefix) (Lombricine Lombricine Lombricine is a phosphagen that is unique to earthworms. Structurally, it is a phosphodiester of the guanidine, 2-guanidinoethanol , and D-serine , which is then further phosphorylated by lombricine kinase to phospholombricine.... )

External links

IUPAC Blue Book (organic nomenclature)
IUPAC ligand abbreviations (pdf)
_chemical_formula_moiety in CIF dictionary
Functional group synthesis from organic-reaction.com