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{{Short description|Group of atoms giving a molecule characteristic properties}}{{Other uses}}{{More citations needed|date=August 2016}}File:Benzyl acetate - functional groups and moieties.svg|thumb|150px|Example functional groups of benzyl acetate:{{legend-line|solid red|Ester group}}{{legend-line|dashed green|Acetyl group}} {{legend-line|dashed orange|Benzyloxy group}}]]In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule’s characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule’s composition.Compendium of Chemical Terminology (IUPAC “Gold Book“) functional group{{March3rd}} This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Functional groups can also be charged, e.g. in carboxylate salts ({{chem2|sCOO-}}), which turns the molecule into a polyatomic ion or a complex ion. Functional groups binding to a central atom in a coordination complex are called ligands. Complexation and solvation are also caused by specific interactions of functional groups. In the common rule of thumb “like dissolves like”, it is the shared or mutually well-interacting functional groups which give rise to solubility. For example, sugar dissolves in water because both share the hydroxyl functional group ({{chem2|sOH}}) and hydroxyls interact strongly with each other. Plus, when functional groups are more electronegative than atoms they attach to, the functional groups will become polar, and the otherwise nonpolar molecules containing these functional groups become polar and so become soluble in some aqueous environment.Combining the names of functional groups with the names of the parent alkanes generates what is termed a systematic nomenclature for naming organic compounds. In traditional nomenclature, the first carbon atom after the carbon that attaches to the functional group is called the alpha carbon; 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-aminobutyric acid is on the third carbon of the carbon chain attached to the carboxylic acid group. IUPAC conventions call for numeric labeling of the position, e.g. 4-aminobutanoic acid. In traditional names various qualifiers are used to label isomers, for example, isopropanol (IUPAC name: propan-2-ol) is an isomer of n-propanol (propan-1-ol). The term moiety has some overlap with the term “functional group”. However, a moiety is an entire “half” of a molecule, which can be not only a single functional group, but also a larger unit consisting of multiple functional groups. For example, an “aryl moiety” may be any group containing an aromatic ring, regardless of how many functional groups the said aryl has.

Table of common functional groups

The following is a list of common functional groups.BOOK, Brown, Theodore, Chemistry: the central science, Prentice Hall, Upper Saddle River, NJ, 2002, 0130669970, 1001, In the formulas, the symbols R and R’ usually denote an attached hydrogen, or a hydrocarbon side chain of any length, but may sometimes refer to any group of atoms.

Hydrocarbons

Hydrocarbons are a class of molecule that is defined by functional groups called (wikt:hydrocarbyl|hydrocarbyl)s that contain only carbon and hydrogen, but vary in the number and order of double bonds. Each one differs in type (and scope) of reactivity.{| class=“wikitable” style="background: #ffffff; text-align: center;width:550px”! Chemical class! Group! Formula! Structural Formula! Prefix! Suffix! Example

Alkane >|Alkyl| R(CH2)nH	75px|Alkyl)	| -ane	135x135px)Ethane

Alkene >	Alkene>Alkenyl| R2C=CR2	75px|Alkene)	| -ene	75px|ethylene)Ethylene(Ethene)

Alkyne >	Alkyne>Alkynyl| RC≡CR’| R-C#C-R’	| -yne| H-C#C-HAcetylene(Ethyne)

Benzene>Benzene derivative| Phenyl| RC6H5RPh	75px|Phenyl)	| -benzene	75px)Cumene(Isopropylbenzene)

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 carbocations or negative carbanions. Carbocations are often named -um. Examples are tropylium and triphenylmethyl cations and the cyclopentadienyl anion.

Groups containing halogen

Haloalkanes are a class of molecule that is defined by a carbon–halogen 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 reactions or elimination reactions. The substitution on the carbon, the acidity of an adjacent proton, the solvent conditions, etc. all can influence the outcome of the reactivity.{| class=“wikitable” style="background: #ffffff; text-align: center;width:550px”! Chemical class! Group! Formula! Structural formula! Prefix! Suffix! Example

haloalkane >	halogen>halo| RX| R-X	| alkyl halide	65x65px)Chloroethane(Ethyl chloride)

fluoroalkane >	fluorine>fluoro| RF| R-F	| alkyl fluoride	92x92px)Fluoromethane(Methyl fluoride)

chloroalkane >	chlorine>chloro| RCl| R-Cl	| alkyl chloride	98x98px|Chloromethane)Chloromethane(Methyl chloride)

bromoalkane >	bromine>bromo| RBr| R-Br	| alkyl bromide	107x107px)Bromomethane(Methyl bromide)

iodoalkane >	iodine>iodo| RI| R-I	| alkyl iodide	75px|Iodomethane)Iodomethane(Methyl iodide)

Groups containing oxygen

Compounds that contain C-O bonds each possess differing reactivity based upon the location and hybridization 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).{| class=“wikitable” style="background: #ffffff; text-align: center;width:300px”! Chemical class! Group! Formula! Structural formula! Prefix! Suffix! Example

Alcohol (chemistry)>Alcohol || Hydroxyl| ROH	60px	Hydroxyl)	| -ol	90px|methanol)Methanol

Ketone >| Ketone| RCOR’	Ketone|75px)	| -one	75px|Butanone)Butanone(Methyl ethyl ketone)

Aldehyde >| Aldehyde| RCHO	75px|Aldehyde)	| -al	75px|acetaldehyde)Acetaldehyde(Ethanal)

Acyl halide >| Haloformyl| RCOX	75px|Acyl halide)	| -oyl fluoride -oyl chloride -oyl bromide -oyl iodide	75px|Acetyl chloride)Acetyl chloride(Ethanoyl chloride)

Carbonate ester>Carbonate| Carbonate ester| ROCOOR’	75px|Carbonate)| (alkoxycarbonyl)oxy-| alkyl carbonate	90px|triphosgene)Triphosgene(bis(trichloromethyl) carbonate)

Carboxylic acid>Carboxylate	Carboxylate >| RCOO−	60px	Carboxylate)(File:Carboxylate-canonical-forms.svg	Carboxylate)	| -oate	75px|Sodium acetate)Sodium acetate(Sodium ethanoate)

| Carboxylic acid

Carboxyl >| RCOOH	75px|Carboxylic acid)	| -oic acid	75px|Acetic acid)Acetic acid(Ethanoic acid)

Ester >	Ester>Carboalkoxy| RCOOR’	Ester|75px)| alkanoyloxy-oralkoxycarbonyl| alkyl alkanoate	75px|Ethyl butyrate)Ethyl butyrate(Ethyl butanoate)

Organic peroxide>Hydroperoxide	Organic peroxide>Hydroperoxy| ROOH	75px|Hydroperoxy)| hydroperoxy-| alkyl hydroperoxide	75px	tert-Butyl hydroperoxide)tert-Butyl hydroperoxide>tert-Butyl hydroperoxide

Organic peroxide>Peroxide	Organic peroxide>Peroxy| ROOR’	75px|Peroxy)| peroxy-| alkyl peroxide	75px|Di-tert-butyl peroxide)Di-tert-butyl peroxide

Ether >| Ether| ROR’	60px	Ether)| alkoxy-| alkyl ether	75px|Diethyl ether)Diethyl ether(Ethoxyethane)

Hemiacetal >| Hemiacetal| R2CH(OR1)(OH)	75px|Hemiacetal)| alkoxy -ol| -al alkyl hemiacetal|

Hemiketal >| Hemiketal| RC(ORʺ)(OH)R’	75px|Hemiketal)| alkoxy -ol| -one alkyl hemiketal|

Acetal >| Acetal| RCH(OR’)(OR“)	75px|Acetal)| dialkoxy-| -al dialkyl acetal|

Ketal (or Acetal) >| Ketal (or Acetal)	RC(OR“)(OR‴)R’}}	75px|Ketal)| dialkoxy-| -one dialkyl ketal|

Orthoester >| Orthoester	RC(OR’)(OR“)(OR‴)}}	75px|Orthoester)| trialkoxy-||

Heterocycle (if cyclic) >| Methylenedioxy	(–OCH2O–)}}|(File:Methylenedioxy graphic (ChemDraw).png|50px|frameless)| methylenedioxy-| -dioxole	75px)1,2-Methylenedioxybenzene(1,3-Benzodioxole)

Orthocarbonate ester >| Orthocarbonate ester	C(OR)(OR’)(OR“)(OR‴)}}	75px|Orthocarbonate ester)| tetralkoxy-| tetraalkyl orthocarbonate| (File:Tetramethylorthocarbonat.svg)Tetramethoxymethane

Organic acid anhydride >| Carboxylic anhydride	R1(CO)O(CO)R2}}	75px|Carboxylic anhydride)|| anhydride	75px|Butyric anhydride)Butyric anhydride

Groups containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.{| class=“wikitable” style="background: #ffffff; text-align: center;width:700px”! Chemical class! Group! Formula! Structural formula! Prefix! Suffix! Example

Amide >| Carboxamide| RCONR’R”	85px|Amide)	| -amide	75px|acetamide)Acetamide(Ethanamide)

|Amidine|Amidine|RC(NR)NR2

frameless|132x132px)| amidino-| -amidine	alt=	86x86px)acetamidine(acetimidamide)

Amines	amine>Primary amine| RNH2	75px|Primary amine)	| -amine	75px|methylamine)Methylamine(Methanamine)

amine>Secondary amine| R’R“NH	75px|Secondary amine)	| -amine	75px|dimethylamine)Dimethylamine

amine>Tertiary amine| R3N	75px|Tertiary amine)	| -amine	75px|trimethylamine)Trimethylamine

Quaternary ammonium cation>4° ammonium ion| R4N+	75px|Quaternary ammonium cation)	| -ammonium	150px|Choline)Choline

|Hydrazone|R’R“CN2H2

thumb|83x83px)|hydrazino-| -hydrazine	thumb	BenzophenoneBenzophenone

Imine	imine>Primary ketimine| RC(=NH)R’	75px|Imine)	| -imine|

imine>Secondary ketimine| RC(=NR’’)R’	75px|Imine)	| -imine|

imine>Primary aldimine| RC(=NH)H	75px|Imine)	| -imine	75px|Ethanimine)Ethanimine

imine>Secondary aldimine| RC(=NR’)H	75px|Imine)	| -imine|

Imide >| Imide| (RCO)2NR’	75px|Imide)| imido-| -imide	75px|Succinimide)Succinimide(Pyrrolidine-2,5-dione)

| Azide| Azide| RN3

75px|Organoazide)	| alkyl azide	75px|Phenyl azide)Phenyl azide(Azidobenzene)

| Azo compound

Azo compound>Azo(Diimide)| RN2R’	75px|Azo.pngl)	| -diazene	150px|Methyl orange)Methyl orange(p-dimethylamino-azobenzenesulfonic acid)

Cyanates	Cyanate >| ROCN	75px|Cyanate)| cyanato-| alkyl cyanate	75px|Methyl cyanate)Methyl cyanate

Isocyanate >| RNCO	75px|Isocyanate)| isocyanato-| alkyl isocyanate	75px|Methyl isocyanate)Methyl isocyanate

Nitrate >| Nitrate| RONO2	75px|Nitrate)	|alkyl nitrate	150px|Amyl nitrate)Amyl nitrate(1-nitrooxypentane)

Nitrile| Nitrile| RCN| R-!#N| cyano-| alkanenitrilealkyl cyanide	75px|Benzonitrile)Benzonitrile(Phenyl cyanide)

Isonitrile >| RNC	thumb| )| isocyano-| alkaneisonitrilealkyl isocyanide| ce{H3C}{-}overset{+}{ce{N}}ce{#C^-}Methyl isocyanide

Alkyl nitrites>Nitrite	Nitrosooxy| RONO	75px|Nitrite)	|alkyl nitrite	150px|Amyl nitrite)Isoamyl nitrite(3-methyl-1-nitrosooxybutane)

| Nitro compound

Nitro functional group>Nitro| RNO2	75px|Nitro)	|	75px|Nitromethane)Nitromethane

Nitroso>Nitroso compound	Nitroso >| RNO	75px|Nitroso)	|	75px|Nitrosobenzene)Nitrosobenzene

| Oxime

Oxime >| RCH=NOH	125px|Oxime)	| Oxime	75px|Acetone oxime)Acetone oxime(2-Propanone oxime)

Pyridine>Pyridine derivative	Pyridine>Pyridyl| RC5H4N|(File:4-pyridyl.svg|75px|4-pyridyl group)(File:3-pyridyl.svg|75px|3-pyridyl group)(File:2-pyridyl.svg|75px|2-pyridyl group)|4-pyridyl(pyridin-4-yl)3-pyridyl(pyridin-3-yl)2-pyridyl(pyridin-2-yl)| -pyridine	75px|Nicotine)Nicotine

Carbamate>Carbamate ester	Carbamate >| RO(C=O)NR2	85px|Carbamate)	| -carbamate	125px|Chlorpropham)Chlorpropham(Isopropyl (3-chlorophenyl)carbamate)

Groups containing sulfur

Compounds that contain sulfur exhibit unique chemistry due to sulfur’s ability to form more bonds than oxygen, its 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.{| class=“wikitable” style="background: #ffffff; text-align: center;width:800px”! Chemical class! Group! Formula! Structural formula! Prefix! Suffix! Example| Thiol

Thiol>Sulfhydryl| RSH	75px|Sulfhydryl)| sulfanyl-(-SH)| -thiol	75px|Ethanethiol)Ethanethiol

Sulfide (organic)>Sulfide(Thioether)	Sulfide (organic)>Sulfide| RSR’	75px|Sulfide group)| substituent sulfanyl-(-SR’)| di(substituent) sulfide	130px|Dimethyl sulfide)(Methylsulfanyl)methane (prefix) orDimethyl sulfide (suffix)

Disulfide bond>Disulfide	Disulfide| RSSR’	75px|Disulfide)| substituent disulfanyl-(-SSR’)| di(substituent) disulfide	130px|Dimethyl disulfide)(Methyldisulfanyl)methane (prefix) orDimethyl disulfide (suffix)

| Sulfoxide

Sulfoxide>Sulfinyl| RSOR’	75px|Sulfinyl group)| -sulfinyl-(-SOR’)| di(substituent) sulfoxide	130px|DMSO)(Methanesulfinyl)methane (prefix) orDimethyl sulfoxide (suffix)

| Sulfone

Sulfone>Sulfonyl| RSO2R’	75px|Sulfonyl group)| -sulfonyl-(-SO2R’)| di(substituent) sulfone	75px|Dimethyl sulfone)(Methanesulfonyl)methane (prefix) orDimethyl sulfone (suffix)

Sulfinic acid >| Sulfino| RSO2H	75px)| sulfino-(-SO2H)| -sulfinic acid	75px|Hypotaurine)2-Aminoethanesulfinic acid

Sulfonic acid >| Sulfo| RSO3H	75px|Sulfonyl group)| sulfo-(-SO3H)| -sulfonic acid	75px|Benzenesulfonic acid)Benzenesulfonic acid

Sulfonate ester >| Sulfo| RSO3R’	75px|Sulfonic ester)| (-sulfonyl)oxy-oralkoxysulfonyl-| R R-sulfonate’	75px|Methyl trifluoromethanesulfonate)Methyl trifluoromethanesulfonate orMethoxysulfonyl trifluoromethane (prefix)

Thiocyanate	Thiocyanate >| RSCN	75px|Thiocyanate)| thiocyanato-(-SCN)| substituent thiocyanate	100px|Phenyl thiocyanate)Phenyl thiocyanate

Isothiocyanate >| RNCS	75px|Isothiocyanate)| isothiocyanato-(-NCS)| substituent isothiocyanate	100px|Allyl isothiocyanate)Allyl isothiocyanate

| Thioketone| Carbonothioyl| RCSR’

60px|Thione)| -thioyl-(-CSR’)orsulfanylidene-(=S)| -thione	75px|Diphenylmethanethione)Diphenylmethanethione(Thiobenzophenone)

| Thial| Carbonothioyl| RCSH

60px|Thial)| methanethioyl-(-CSH)orsulfanylidene-(=S)| -thial|

Thiocarboxylic acid| Carbothioic S-acid| RC=OSH	60px	Thioic S-acid)| mercaptocarbonyl-| -thioic S-acid	75px|Thiobenzoic acid)Thiobenzoic acid(benzothioic S-acid)

| Carbothioic O-acid| RC=SOH

60px	Thioic O-acid)| hydroxy(thiocarbonyl)-| -thioic O-acid|

Thioester| Thiolester| RC=OSR’	75px|Thiolester)|| S-alkyl-alkane-thioate	75px|S-methyl thioacrylate)S-methyl thioacrylate(S-methyl prop-2-enethioate)

| Thionoester| RC=SOR’

75px|Thionoester)|| O-alkyl-alkane-thioate|

Thiocarboxylic acid#Dithiocarboxylic acids>Dithiocarboxylic acid| Carbodithioic acid| RCS2H	60px	Dithiocarboxylic acid)| dithiocarboxy-| -dithioic acid	75px|Dithiobenzoic acid)Dithiobenzoic acid(Benzenecarbodithioic acid)

| Dithiocarboxylic acid ester| Carbodithio| RC=SSR’

75px|Dithioate)|| -dithioate|

Groups containing phosphorus

Compounds that contain phosphorus exhibit unique chemistry due to the ability of phosphorus to form more bonds than nitrogen, its lighter analogue on the periodic table.{| class=“wikitable” style="background: #ffffff; text-align: center;width:800px”! Chemical class! Group! Formula! Structural formula! Prefix! Suffix! Example

Phosphine(Phosphane) >| Phosphino| R3P	75px|A tertiary phosphine)	| -phosphane	75px|Methylpropylphosphane)Methylpropylphosphane

| Phosphonic acid| Phosphono| RP(=O)(OH)2

75px|Phosphono group)| phosphono-| substituent phosphonic acid	75px|Benzylphosphonic acid)Benzylphosphonic acid

Phosphate	Phosphate	ROP(=O)(OH)2	(File:Phosphate-group.svg	Phosphate group)	phosphonooxy-orO-phosphono- (phospho-)	substituent phosphate	75px	Glyceraldehyde 3-phosphate>Glyceraldehyde 3-phosphate (suffix)

75px|Phosphocholine)O-Phosphonocholine (prefix)(Phosphocholine)

Phosphodiester	Phosphate	HOPO(OR)2	(File:Phosphodiester-group.svg	Phosphodiester)	[(alkoxy)hydroxyphosphoryl]oxy-orO-[(alkoxy)hydroxyphosphoryl]-	di(substituent) hydrogen phosphateorphosphoric acid di(substituent) ester| DNA

O‑[(2‑Guanidinoethoxy)hydroxyphosphoryl]‑{{Smallcaps>l}}‑serine (prefix)(Lombricine)

Groups containing boron

Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as Lewis acids.{| class=“wikitable”! Chemical class !! Group !! Formula !! Structural formula !! Prefix !! Suffix !! Example

Boronic acid >			70px			substituentboronic acid >	(File:Phenylboronic acid.png	Phenylboronic acid)Phenylboronic acid}}

Boronic acid#Boronic esters (also named boronate esters)>Boronic ester	Boronate	RB(OR)2	(File:Boronate-ester-2D.svg	center)	O-[bis(alkoxy)alkylboronyl]-	substituentboronic aciddi(substituent) ester

Borinic acid >			70px			substituent)borinic acid >|

Boronic acid#Borinic acids and esters>Borinic ester	Borinate	R2BOR	(File:Borinate-ester-2D.svg	center)	O-[alkoxydialkylboronyl]-	di(substituent)borinic acidsubstituent ester	{{center	140px|2-Aminoethoxydiphenyl borate)Diphenylborinic acid 2-aminoethyl ester(2-Aminoethoxydiphenyl borate)}}

Groups containing metals {| class“wikitable“|+

!Chemical class!Structural formula!Prefix!Suffix!Example

Organolithium reagent>Alkyllithium|RLi	(tri/di)alkyl-| -lithium	71x71px)methyllithium

Grignard reagent>Alkylmagnesium halide	halogen	note 1}}| -magnesium halide	97x97px)methylmagnesium chloride

|Alkylaluminium|Al2R6| -aluminium

109x109px)trimethylaluminium

|Silyl ether|R3SiOR| -silyl ether|(File:Trimethylsilyl triflate.svg)trimethylsilyl triflate{{Note label|halogen|note 1|note 1}} Fluorine is too electronegative to be bonded to magnesium; it becomes an ionic salt instead.

Names of radicals or moieties

These names are used to refer to the moieties themselves or to radical species, and also to form the names of halides and substituents in larger molecules.When the parent hydrocarbon is unsaturated, the suffix (“-yl”, “-ylidene”, or “-ylidyne“) replaces “-ane” (e.g. “ethane” becomes “ethyl“); otherwise, the suffix replaces only the final “-e” (e.g. “ethyne” becomes “ethynyl“).When used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a methylene bridge (methanediyl) has two single bonds, whereas a methylene group (methylidene) has one double bond. Suffixes can be combined, as in methylidyne (triple bond) vs. methylylidene (single bond and double bond) vs. methanetriyl (three double bonds).There are some retained names, such as methylene for methanediyl, 1,x-phenylene for phenyl-1,x-diyl (where x is 2, 3, or 4),WEB,www.acdlabs.com/iupac/nomenclature/93/r93_271.htm, R-2. 5 Substituent Prefix Names Derived from Parent Hydrides, IUPAC, 1993, section P-56.2.1 carbyne for methylidyne, and trityl for triphenylmethyl.{| class=“wikitable”! Chemical class !! Group !! Formula !! Structural formula !! Prefix !! Suffix !! Example

					ACCESS-DATE=2014-12-02	ARCHIVE-DATE=2017-06-11			Methyl groupMethyl radical}}

						Methylidene}}

						Methylidyne}}

acyl radical >						Acetyl}}

See also

• (:Category:Functional groups)
• Group contribution method

References

External links

{{Commons|Functional groups}}

• IUPAC Blue Book (organic nomenclature)
• WEB,www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf, IUPAC ligand abbreviations, 2 April 2004, IUPAC, 25 February 2015,www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf," title="web.archive.org/web/20070927121055www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf,">web.archive.org/web/20070927121055www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf, 27 September 2007,
• Functional group video

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