functional group

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functional group
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{{other uses}}{{refimprove|date=August 2016}}Image:Benzyl acetate - functional groups and moieties.svg|thumb|150px|Benzyl acetateBenzyl acetateIn organic chemistry, functional groups are specific substituents or moieties within molecules that are responsible for the characteristic chemical reactions 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.Compendium of Chemical Terminology (IUPAC "Gold Book") functional group{{JerryMarch}} This allows for systematic prediction of chemical reactions and behavior of chemical compounds and design of chemical syntheses. Furthermore, the reactivity of a functional group can be modified by other functional groups nearby. In organic synthesis, functional group interconversion is one of the basic types of transformations. Functional groups are groups of one or more atoms of distinctive chemical properties no matter what they are attached to. The atoms of functional groups 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 (–COO−), 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 (–OH) 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).

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.


Functional groups, called (wikt:hydrocarbyl|hydrocarbyl), 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 Formulae! Prefix! Suffix! Example
Alkane >Alkane>Alkyl| R(CH2)nHAlkyl| -ane135x135px)Ethane
Alkene >Alkene>Alkenyl| R2C=CR2Alkene| -eneethyleneEthylene(Ethene)
Alkyne >Alkyne>Alkynyl| RC≡CR'| R-C#C-R'| -yne| H-C#C-HAcetylene(Ethyne)
Benzene>Benzene derivative| Phenyl| RC6H5RPhPhenyl| -benzene110x110px)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 halide65x65px)Chloroethane(Ethyl chloride)
fluoroalkane >fluorine>fluoro| RF| R-F| alkyl fluoride92x92px)Fluoromethane(Methyl fluoride)
chloroalkane >chlorine>chloro| RCl| R-Cl| alkyl chlorideChloromethaneChloromethane(Methyl chloride)
bromoalkane >bromine>bromo| RBr| R-Br| alkyl bromide107x107px)Bromomethane(Methyl bromide)
iodoalkane >iodine>iodo| RI| R-I| alkyl iodideIodomethaneIodomethane(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
|| Hydroxyl| ROH
60px Hydroxyl| -olmethanolMethanol
Ketone >| Carbonyl| RCOR'Ketone|75px)| -oneButanoneButanone(Methyl ethyl ketone)
Aldehyde >| Aldehyde| RCHOAldehyde| -alacetaldehydeAcetaldehyde(Ethanal)
Acyl halide >| Haloformyl| RCOXAcyl halide| -oyl halideAcetyl chlorideAcetyl chloride(Ethanoyl chloride)
Carbonate ester>Carbonate| Carbonate ester| ROCOOR'Carbonate| (alkoxycarbonyl)oxy-| alkyl carbonatetriphosgeneTriphosgene(bis(trichloromethyl) carbonate)
Carboxylic acid>CarboxylateCarboxylate >| RCOO−Image:Carboxylate-resonance-hybrid.svg>60pxCarboxylate75px|Carboxylate| -oateSodium acetateSodium acetate(Sodium ethanoate)
| Carboxylic acid
Carboxyl >| RCOOHCarboxylic acid| -oic acidAcetic acidAcetic acid(Ethanoic acid)
Ester >| Ester| RCOOR'75px| alkanoyloxy-oralkoxycarbonyl| alkyl alkanoateEthyl butyrateEthyl butyrate(Ethyl butanoate)
Methoxy >| Methoxy| ROCH3Methoxy| methoxy-|AnisoleAnisole(Methoxybenzene)
Organic peroxide>HydroperoxideOrganic peroxide>Hydroperoxy| ROOHHydroperoxy| hydroperoxy-| alkyl hydroperoxide75pxtert-Butyl hydroperoxide)tert-Butyl hydroperoxide>tert-Butyl hydroperoxide
Organic peroxide>PeroxideOrganic peroxide>Peroxy| ROOR'Peroxy| peroxy-| alkyl peroxideDi-tert-butyl peroxideDi-tert-butyl peroxide
Ether >| Ether| ROR'Image:Ether-(general).svg>60pxEther| alkoxy-| alkyl etherDiethyl etherDiethyl ether(Ethoxyethane)
Hemiacetal >| Hemiacetal| RCH(OR')(OH)Hemiacetal| alkoxy -ol| -al alkyl hemiacetal|
Hemiketal >| Hemiketal| RC(ORʺ)(OH)R'75px|Hemiketal)| alkoxy -ol| -one alkyl hemiketal|
Acetal >| Acetal| RCH(OR')(OR")Acetal| dialkoxy-| -al dialkyl acetal|
Ketal (or Acetal) >| Ketal (or Acetal)RC(ORʺ)(OR‴)R'}}75px|Ketal)| dialkoxy-| -one dialkyl ketal|
Orthoester >| OrthoesterRC(OR')(ORʺ)(OR‴)}}75px|Orthoester)| trialkoxy-| |
Heterocycle >| MethylenedioxyPhOCOPh}}75px|Methylenedioxy chemical structure.)| methylenedioxy-| -dioxole75px)1,2-Methylenedioxybenzene(1,3-Benzodioxole)
Orthocarbonate ester >| Orthocarbonate esterC(OR)(OR')(ORʺ)(OR″)}}75px|Orthocarbonate ester)| tetralkoxy-| tetraalkyl orthocarbonate| (File:Tetramethylorthocarbonat.svg) Tetramethoxymethane

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| RCONR2Amide| -amideacetamideAcetamide(Ethanamide)
Aminesamine>Primary amine| RNH2Primary amine| -aminemethylamineMethylamine(Methanamine)
amine>Secondary amine| R2NHSecondary amine| -aminedimethylamineDimethylamine
amine>Tertiary amine| R3NTertiary amine| -aminetrimethylamineTrimethylamine
Quaternary ammonium cation>4° ammonium ion| R4N+Quaternary ammonium cation| -ammoniumcholineCholine
Imineimine>Primary ketimine| RC(=NH)R'Imine| -imine|
imine>Secondary ketimine| RC(=NR'')R'Imine| -imine|
imine>Primary aldimine| RC(=NH)HImine| -imineEthanimineEthanimine
imine>Secondary aldimine| RC(=NR')HImine| -imine|
Imide >| Imide| (RCO)2NR'Imide| imido-| -imideSuccinimideSuccinimide(Pyrrolidine-2,5-dione)
| Azide| Azide| RN3
Organoazide| alkyl azidePhenyl azidePhenyl azide(Azidobenzene)
| Azo compound
Azo compound>Azo(Diimide)| RN2R'Azo.pngl| -diazeneMethyl orangeMethyl orange(p-dimethylamino-azobenzenesulfonic acid)
CyanatesCyanate >| ROCNCyanate| cyanato-| alkyl cyanateMethyl cyanateMethyl cyanate
Isocyanate >| RNCOIsocyanate| isocyanato-| alkyl isocyanateMethyl isocyanateMethyl isocyanate
Nitrate >| Nitrate| RONO2Nitrate| alkyl nitrateAmyl nitrateAmyl nitrate(1-nitrooxypentane)
Nitrile | Nitrile| RCN| R-!#N| cyano-| alkanenitrilealkyl cyanideBenzonitrileBenzonitrile(Phenyl cyanide)
Isonitrile >| RNC| ce{R}{-}overset{+}{ce{N}}ce{#C^-}| isocyano-| alkaneisonitrilealkyl isocyanide| ce{H3C}{-}overset{+}{ce{N}}ce{#C^-}Methyl isocyanide
Nitrite >Nitrite>Nitrosooxy| RONONitrite|alkyl nitriteAmyl nitriteIsoamyl nitrite(3-methyl-1-nitrosooxybutane)
| Nitro compound
Nitro functional group>Nitro| RNO2Nitro|  NitromethaneNitromethane
Nitroso>Nitroso compoundNitroso >| RNONitroso|  NitrosobenzeneNitrosobenzene
| Oxime
Oxime >| RCH=NOHOxime| OximeAcetone oximeAcetone oxime(2-Propanone oxime)
Pyridine>Pyridine derivativePyridine>Pyridyl| RC5H4N| 75px|4-pyridyl group75px|3-pyridyl group75px|2-pyridyl group| 4-pyridyl(pyridin-4-yl)3-pyridyl(pyridin-3-yl)2-pyridyl(pyridin-2-yl)| -pyridineNicotineNicotine
Carbamate>Carbamate esterCarbamate >| RO(C=O)NR285px|Carbamate)| -carbamate125px|Chlorpropham)Chlorpropham(Isopropyl (3-chlorophenyl)carbamate)

Groups containing sulfur

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.{| class="wikitable" style="background: #ffffff; text-align: center;width:800px"! Chemical class! Group! Formula! Structural Formula! Prefix! Suffix! Example
| Thiol
Thiol>Sulfhydryl| RSHSulfhydryl| sulfanyl-(-SH)| -thiolEthanethiolEthanethiol
| Sulfide(Thioether)| Sulfide| RSR'
Sulfide group| substituent sulfanyl-(-SR')| di(substituentsulfideDimethyl sulfide(Methylsulfanyl)methane (prefix) orDimethyl sulfide (suffix)
Disulfide bond>Disulfide Disulfide| RSSR'Disulfide | substituent disulfanyl-(-SSR')| di(substituentdisulfideDimethyl disulfide(Methyldisulfanyl)methane (prefix) orDimethyl disulfide (suffix)
| Sulfoxide
Sulfoxide>Sulfinyl| RSOR'Sulfinyl group| -sulfinyl-(-SOR')| di(substituentsulfoxideDMSO(Methanesulfinyl)methane (prefix) orDimethyl sulfoxide (suffix)
| Sulfone
Sulfone>Sulfonyl| RSO2R'Sulfonyl group| -sulfonyl-(-SO2R')| di(substituentsulfoneDimethyl sulfone(Methanesulfonyl)methane (prefix) orDimethyl sulfone (suffix)
Sulfinic acid >| Sulfino| RSO2HImage:Sulfinic-acid-2D.svg>75px| sulfino-(-SO2H)| -sulfinic acidHypotaurine2-Aminoethanesulfinic acid
Sulfonic acid >| Sulfo| RSO3HSulfonyl group| sulfo-(-SO3H)| -sulfonic acidBenzenesulfonic acidBenzenesulfonic acid
Sulfonate ester >| Sulfo| RSO3R'Sulfonic ester| (-sulfonyl)oxy- oralkoxysulfonyl-| R R-sulfonate'Methyl trifluoromethanesulfonateMethyl trifluoromethanesulfonate or Methoxysulfonyl trifluoromethane (prefix)
Thiocyanate Thiocyanate >| RSCNThiocyanate| thiocyanato-(-SCN)| substituent thiocyanatePhenyl thiocyanatePhenyl thiocyanate
Isothiocyanate >| RNCSIsothiocyanate| isothiocyanato-(-NCS)| substituent isothiocyanateAllyl isothiocyanateAllyl isothiocyanate
| Thioketone| Carbonothioyl| RCSR'
Thione| -thioyl-(-CSR')orsulfanylidene-(=S)| -thioneDiphenylmethanethioneDiphenylmethanethione(Thiobenzophenone)
| Thial| Carbonothioyl| RCSH
Thial| methanethioyl-(-CSH)orsulfanylidene-(=S)| -thial|
Thiocarboxylic acid| Carbothioic S-acid | RC=OSH 60pxThioic S-acid)| mercaptocarbonyl-| -thioic S-acid75px|Thiobenzoic acid)Thiobenzoic acid(benzothioic S-acid)
| Carbothioic O-acid | RC=SOH
60pxThioic O-acid) | hydroxy(thiocarbonyl)-| -thioic O-acid|
Thioester| Thiolester | RC=OSR' 75px|Thiolester)|| S-alkyl-alkane-thioate75px|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 60pxDithiocarboxylic acid)| dithiocarboxy-| -dithioic acid75px|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 their ability to form more bonds than nitrogen, their lighter analogues 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| R3PA tertiary phosphine| -phosphaneMethylpropylphosphaneMethylpropylphosphane
| Phosphonic acid | Phosphono| RP(=O)(OH)2
Phosphono group| phosphono-| substituent phosphonic acidBenzylphosphonic acidBenzylphosphonic acid
Phosphate Phosphate ROP(=O)(OH)2 Image:Phosphate-group.svgPhosphate group phosphonooxy-orO-phosphono- (phospho-) substituent phosphateImage:G3P-2D-skeletal.png>75pxGlyceraldehyde 3-phosphate>Glyceraldehyde 3-phosphate (suffix)
PhosphocholineO-Phosphonocholine (prefix)(Phosphocholine)
PhosphodiesterPhosphateHOPO(OR)2Image:Phosphodiester-group.svgPhosphodiester[(alkoxy)hydroxyphosphoryl]oxy-orO-[(alkoxy)hydroxyphosphoryl]-di(substituent) hydrogen phosphateorphosphoric acid di(substituentester| 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 >Image:Boronic-acid-2D.svg>70px >substituentboronic acid >Phenylboronic acidPhenylboronic acid
Boronic acid#Boronic esters (also named boronate esters)>Boronic ester Boronate RB(OR)2 Image:Boronate-ester-2D.svgcenter O-[bis(alkoxy)alkylboronyl]- substituentboronic aciddi(substituent) ester
Borinic acid >Image:Borinic-acid-2D.svg>70px >substituent)borinic acid >|
Boronic acid#Borinic acids and esters>Borinic ester Borinate R2BOR Image:Borinate-ester-2D.svgcenter O-[alkoxydialkylboronyl]- di(substituent)borinic acidsubstituent ester Image:2-APB.png2-Aminoethoxydiphenyl borateDiphenylborinic acid 2-aminoethyl ester(2-Aminoethoxydiphenyl borate)

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").Note that 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,weblink 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
| Methyl groupMethyl radical
| Methylidene
| Methylidyne
acyl radical >| Acetyl

See also


External links

{{Functional Groups}}{{Organic chemistry}}{{Authority control}}

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