Functional Group - Wikipedia, The Free Encyclopedia

7/29/2019 Functional Group - Wikipedia, The Free Encyclopedia

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Benzyl acetate has an

ester functional group (inred), an acetyl moiety

(circled with green) and a

benzyloxy moiety (circled

with orange). Other

divisions can be made.

Functional groupFrom Wikipedia, the free encyclopedia

In organic chemistry, functional groups are lexicon-specific groups of atoms or bonds 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.[1][2] However, its relative reactivity can be modified by nearby functional groups.

The word moiety (pron .: / mti/) is often used synonymously with "functional group," but, according to the IUPAC definition,[3] a

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

an ester (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 functional group within the acyl moiety.

Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming

organic compounds.

The atoms of functional groups are linked to each other and to the rest of the molecule by covalent bonds. When the group of covalently

bound atoms bears a net charge, the group is referred to more properly as a polyatomic ion 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, the resulting fragment radicals are referred as free radicals.

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-aminobutanoic acid is on the third carbon of the carbon

chain attached to the carboxylic acid group.

Contents

1 Synthetic chemistry

2 Crystallography

3 Functionalization

4 Table of common functional groups

4.1 Hydrocarbons

4.2 Groups containing halogens

4.3 Groups containing oxygen

4.4 Groups containing nitrogen

4.5 Groups containing sulfur

4.6Groups containing phosphorus

4.7 Groups containing boron

5 See also

6 References

7 External links

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) from the unfunctionalized alkane isobutane (a 4-carbon gas), isobutane is first dehydrogenated into isobutene. This contains the alkene

functional group and can now dimerize with another isobutene to give iso-octene, which is then catalytically hydrogenated to iso-octane using pressured hydrogen gas.

CrystallographyThe International Union of Crystallography in its Crystallographic Information File dictionary defines "moiety" to represent discrete non-bonded components. Thus,

Na2SO4 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.

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 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.
http://en.wikipedia.org/wiki/Microarrayshttp://en.wikipedia.org/wiki/Microelectromechanical_systemshttp://en.wikipedia.org/wiki/Surface_modificationhttp://en.wikipedia.org/wiki/Dimer_(chemistry)http://en.wikipedia.org/wiki/Hydrogenationhttp://en.wikipedia.org/wiki/Hydrogenhttp://en.wikipedia.org/wiki/Functional_group#See_alsohttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_phosphorushttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_nitrogenhttp://en.wikipedia.org/wiki/Functional_group#Crystallographyhttp://en.wikipedia.org/wiki/Ionhttp://en.wikipedia.org/wiki/Alkanehttp://en.wikipedia.org/wiki/Carboxylatehttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Functional_group#cite_note-1http://en.wikipedia.org/wiki/Functional_group#cite_note-2http://en.wikipedia.org/wiki/Organic_chemistryhttp://en.wikipedia.org/wiki/EDTAhttp://en.wikipedia.org/wiki/Microelectromechanical_systemshttp://en.wikipedia.org/wiki/Microarrayshttp://en.wikipedia.org/wiki/Surface_modificationhttp://en.wikipedia.org/wiki/Crystallographic_Information_Filehttp://en.wikipedia.org/wiki/International_Union_of_Crystallographyhttp://en.wikipedia.org/wiki/Hydrogenhttp://en.wikipedia.org/wiki/Hydrogenationhttp://en.wikipedia.org/wiki/Dimer_(chemistry)http://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Isobutenehttp://en.wikipedia.org/wiki/Dehydrogenationhttp://en.wikipedia.org/wiki/Gasolinehttp://en.wikipedia.org/wiki/Iso-octanehttp://en.wikipedia.org/wiki/Functional_group#External_linkshttp://en.wikipedia.org/wiki/Functional_group#Referenceshttp://en.wikipedia.org/wiki/Functional_group#See_alsohttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_boronhttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_phosphorushttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_sulfurhttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_nitrogenhttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_oxygenhttp://en.wikipedia.org/wiki/Functional_group#Groups_containing_halogenshttp://en.wikipedia.org/wiki/Functional_group#Hydrocarbonshttp://en.wikipedia.org/wiki/Functional_group#Table_of_common_functional_groupshttp://en.wikipedia.org/wiki/Functional_group#Functionalizationhttp://en.wikipedia.org/wiki/Functional_group#Crystallographyhttp://en.wikipedia.org/wiki/Functional_group#Synthetic_chemistryhttp://en.wikipedia.org/wiki/Alpha_carbonhttp://en.wikipedia.org/wiki/Carbonhttp://en.wikipedia.org/wiki/Free_radicalshttp://en.wikipedia.org/wiki/Homolysishttp://en.wikipedia.org/wiki/Complex_ionhttp://en.wikipedia.org/wiki/Polyatomic_ionhttp://en.wikipedia.org/wiki/Ionhttp://en.wikipedia.org/wiki/Covalent_bondhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Systematic_namehttp://en.wikipedia.org/wiki/Alkanehttp://en.wikipedia.org/wiki/Phenolhttp://en.wikipedia.org/wiki/Methyl_para-hydroxybenzoatehttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Carboxylatehttp://en.wikipedia.org/wiki/Acylhttp://en.wikipedia.org/wiki/Alkoxyhttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Functional_group#cite_note-3http://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistryhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wiktionary.org/wiki/moietyhttp://en.wikipedia.org/wiki/Functional_group#cite_note-2http://en.wikipedia.org/wiki/Functional_group#cite_note-1http://en.wikipedia.org/wiki/Chemical_reactionhttp://en.wikipedia.org/wiki/Moleculehttp://en.wikipedia.org/wiki/Atomhttp://en.wikipedia.org/wiki/Lexiconhttp://en.wikipedia.org/wiki/Organic_chemistryhttp://en.wikipedia.org/wiki/Benzyl_acetatehttp://en.wikipedia.org/wiki/File:Benzyl_acetate_-_functional_groups_and_moieties.svg


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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 side chain 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 bonds. Each one differs in type (and scope) of

reactivity.

Chemical

class Group FormulaStructural

Formula Prefix Suffix Example

Alkane Alkyl R(CH2)nH alkyl- -ane

Ethane

Alkene Alkenyl R2C=CR2 alkenyl- -ene

Ethylene

(Ethene)

Alkyne Alkynyl RCCR' alkynyl- -yne Acetylene

(Ethyne)

Benzene

derivativePhenyl

RC6H5RPh

phenyl- -benzene

Cumene

(2-

phenylpropane)

Toluenederivative Benzyl RCH2C6H5RBn benzyl- 1-(substituent)toluene Benzyl bromide

(-

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 carbocations or negative carbanions. Carbocations are often named -um. Examples are tropylium and

triphenylmethyl cations and the cyclopentadienyl anion.

Groups containing halogens

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.
http://en.wikipedia.org/wiki/Elimination_reactionhttp://en.wikipedia.org/wiki/Nucleophilic_substitutionhttp://en.wikipedia.org/wiki/Fluorinatedhttp://en.wikipedia.org/wiki/Halogenhttp://en.wikipedia.org/wiki/Cyclopentadienylhttp://en.wikipedia.org/w/index.php?title=Triphenylmethyl&action=edit&redlink=1http://en.wikipedia.org/wiki/Tropyliumhttp://en.wikipedia.org/wiki/Carbanionhttp://en.wikipedia.org/wiki/Carbocationhttp://en.wikipedia.org/wiki/Cyclohexylhttp://en.wikipedia.org/wiki/Bornylhttp://en.wikipedia.org/wiki/Tert-butylhttp://en.wikipedia.org/wiki/Benzyl_bromidehttp://en.wikipedia.org/wiki/File:Benzyl-bromide-skeletal.svghttp://en.wikipedia.org/wiki/File:Benzyl-group.pnghttp://en.wikipedia.org/wiki/Benzylhttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Cumenehttp://en.wikipedia.org/wiki/File:Cumene-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Phenyl-group.pnghttp://en.wikipedia.org/wiki/Phenylhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Acetylenehttp://en.wikipedia.org/wiki/File:Acetylene-2D.svghttp://en.wikipedia.org/wiki/File:Alkyne-(general)-skeletal.pnghttp://en.wikipedia.org/wiki/Alkynehttp://en.wikipedia.org/wiki/Alkynehttp://en.wikipedia.org/wiki/Ethylenehttp://en.wikipedia.org/wiki/File:Ethylene.svghttp://en.wikipedia.org/wiki/File:Alkene-(general)-skeletal.pnghttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Alkenehttp://en.wikipedia.org/wiki/Ethanehttp://en.wikipedia.org/wiki/File:Ethane-2D.pnghttp://en.wikipedia.org/wiki/File:Alkyl-(general)-skeletal.svghttp://en.wikipedia.org/wiki/Alkanehttp://en.wikipedia.org/wiki/Alkanehttp://en.wikipedia.org/wiki/Chemical_classhttp://en.wiktionary.org/wiki/hydrocarbylhttp://en.wikipedia.org/wiki/Side_chainhttp://en.wikipedia.org/wiki/Hydrocarbon


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Chemical

classGroup Formula

Structural

FormulaPrefix Suffix Example

haloalkane halo RX halo-alkyl

halideChloroethane

(Ethyl

chloride)

fluoroalkane fluoro RF fluoro-

alkyl

fluorideFluoromethane

(Methyl

fluoride)

chloroalkane chloro RCl chloro-alkyl

chlorideChloromethane

(Methyl

chloride)

bromoalkane bromo RBr bromo- alkylbromide Bromomethane

(Methyl

bromide)

iodoalkane iodo RI iodo-alkyl

iodide 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).

Chemical

classGroup Formula

Structural


Alcohol Hydroxyl ROH hydroxy- -ol

Methanol

Ketone Carbonyl RCOR'

-oyl- (-COR')

or

oxo- (=O)

-oneButanone

(Methyl ethyl

ketone)

Aldehyde Aldehyde RCHO

formyl- (-COH)

or

oxo- (=O)

-al

Acetaldehyde

(Ethanal)

Acyl halide Haloformyl RCOX

carbonofluoridoyl-

carbonochloridoyl-carbonobromidoyl-

carbonoiodidoyl-

-oyl halide

Acetyl chloride

(Ethanoyl chloride)

Carbonate
http://en.wikipedia.org/wiki/File:Triphosgene-skeletal.pnghttp://en.wikipedia.org/wiki/Carbonate_esterhttp://en.wikipedia.org/wiki/Acetyl_chloridehttp://en.wikipedia.org/wiki/File:Acetyl-chloride.pnghttp://en.wikipedia.org/wiki/File:Acyl-halide-skeletal.pnghttp://en.wikipedia.org/wiki/Acyl_halidehttp://en.wikipedia.org/wiki/Acetaldehydehttp://en.wikipedia.org/wiki/File:Acetaldehyde-skeletal.svghttp://en.wikipedia.org/wiki/File:Aldehyde-skeletal.pnghttp://en.wikipedia.org/wiki/Aldehydehttp://en.wikipedia.org/wiki/Aldehydehttp://en.wikipedia.org/wiki/Butanonehttp://en.wikipedia.org/wiki/File:Butanone-structure-skeletal.pnghttp://en.wikipedia.org/wiki/File:Ketone-group-2D-skeletal.svghttp://en.wikipedia.org/wiki/Carbonylhttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Methanolhttp://en.wikipedia.org/wiki/File:Methanol-2D.pnghttp://en.wikipedia.org/wiki/File:Alcohol-(general)-skeletal.pnghttp://en.wikipedia.org/wiki/Hydroxylhttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Chemical_classhttp://en.wikipedia.org/wiki/Orbital_hybridisationhttp://en.wikipedia.org/wiki/Iodomethanehttp://en.wikipedia.org/wiki/File:Iodomethane.svghttp://en.wikipedia.org/wiki/File:Iodo-group.pnghttp://en.wikipedia.org/wiki/Iodinehttp://en.wikipedia.org/wiki/Iodoalkanehttp://en.wikipedia.org/wiki/Bromomethanehttp://en.wikipedia.org/wiki/File:Bromomethane-2D.pnghttp://en.wikipedia.org/wiki/File:Bromo-group.pnghttp://en.wikipedia.org/wiki/Brominehttp://en.wikipedia.org/wiki/Bromoalkanehttp://en.wikipedia.org/wiki/Chloromethanehttp://en.wikipedia.org/wiki/File:Chloromethane.svghttp://en.wikipedia.org/wiki/File:Chloro-group.pnghttp://en.wikipedia.org/wiki/Chlorinehttp://en.wikipedia.org/wiki/Chloroalkanehttp://en.wikipedia.org/wiki/Fluoromethanehttp://en.wikipedia.org/wiki/File:Fluoromethane-2D.pnghttp://en.wikipedia.org/wiki/File:Fluoro-group.pnghttp://en.wikipedia.org/wiki/Fluorinehttp://en.wikipedia.org/wiki/Fluoroalkanehttp://en.wikipedia.org/wiki/Chloroethanehttp://en.wikipedia.org/wiki/File:Chloroethane-skeletal.pnghttp://en.wikipedia.org/wiki/File:Halide-group.pnghttp://en.wikipedia.org/wiki/Halogenhttp://en.wikipedia.org/wiki/Haloalkanehttp://en.wikipedia.org/wiki/Chemical_class


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Carbonate ester ROCOOR (alkoxycarbonyl)oxy- alkyl carbonate Triphosgene

(bis(trichloromethyl)

carbonate)

Carboxylate Carboxylate RCOO carboxy- -oateSodium acetate

(Sodium ethanoate)

Carboxylic acid Carboxyl RCOOH carboxy- -oic acid

Acetic acid

(Ethanoic acid)

Ester Ester RCOOR'

alkanoyloxy-

or

alkoxycarbonyl

alkyl alkanoate Ethyl butyrate

(Ethyl butanoate)

Methoxy Methoxy ROCH3 methoxy-

Hydroperoxide Hydroperoxy ROOH hydroperoxy-alkyl

hydroperoxideMethyl ethyl ketoneperoxide

Peroxide Peroxy ROOR peroxy- alkyl peroxide

Di-tert-butyl peroxide

Ether Ether ROR' alkoxy- alkyl ether Diethyl ether

(Ethoxyethane)

Hemiacetal Hemiacetal RCH(OR')(OH) alkoxy -ol-al alkyl

hemiacetal

Hemiketal Hemiketal RC(OR)(OH)R' alkoxy -ol-one alkyl

hemiketal

Acetal Acetal RCH(OR')(OR") dialkoxy--al dialkyl

acetal

Ketal (or

Acetal)

Ketal (or

Acetal)RC(OR)(OR)R' dialkoxy-

-one dialkyl

ketal

Orthoester Orthoester RC(OR')(OR)(OR) trialkoxy-

Orthocarbonate

ester

Orthocarbonate

esterC(OR)(OR')(OR)(OR) tetralkoxy-

tetraalkyl

orthocarbonate

Groups containing nitrogen

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

Chemical

classGroup Formula

Structural


Amide Carboxamide RCONR2

carboxamido-

or

carbamoyl-

-amide

Acetamide

(Ethanamide)

Primary

amineRNH2 amino- -amine

Methylamine

(Methanamine)
http://en.wikipedia.org/wiki/Methylaminehttp://en.wikipedia.org/wiki/File:Methylamine-2D.pnghttp://en.wikipedia.org/wiki/File:1%C2%B0-amino-group.pnghttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Acetamidehttp://en.wikipedia.org/wiki/File:Acetamide_skeletal.svghttp://en.wikipedia.org/wiki/File:Amide-(tertiary)-skeletal.pnghttp://en.wikipedia.org/wiki/Carboxamidehttp://en.wikipedia.org/wiki/Amidehttp://en.wikipedia.org/wiki/Chemical_classhttp://en.wikipedia.org/wiki/Amidehttp://en.wikipedia.org/wiki/Orthocarbonate_esterhttp://en.wikipedia.org/wiki/Orthocarbonate_esterhttp://en.wikipedia.org/wiki/File:Orthoester_general_structure.svghttp://en.wikipedia.org/wiki/Orthoesterhttp://en.wikipedia.org/wiki/Orthoesterhttp://en.wikipedia.org/wiki/File:Ketal-2D-skeletal.pnghttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/Ketalhttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/Ketalhttp://en.wikipedia.org/wiki/File:Generic_Acetal.pnghttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/Acetalhttp://en.wikipedia.org/wiki/File:Hemiketal-2D-skeletal.pnghttp://en.wikipedia.org/wiki/Hemiketalhttp://en.wikipedia.org/wiki/Hemiketalhttp://en.wikipedia.org/wiki/File:Hemiacetal-2D-skeletal.pnghttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Hemiacetalhttp://en.wikipedia.org/wiki/Diethyl_etherhttp://en.wikipedia.org/wiki/File:Diethyl-ether-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Ether-(general).pnghttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Etherhttp://en.wikipedia.org/wiki/Di-tert-butyl_peroxidehttp://en.wikipedia.org/wiki/File:DTBP.pnghttp://en.wikipedia.org/wiki/File:Peroxy-group.pnghttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Methyl_ethyl_ketone_peroxidehttp://en.wikipedia.org/wiki/File:Methyl-ethyl-ketone-peroxide-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Hydroperoxide-group-2D.pnghttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/Organic_peroxidehttp://en.wikipedia.org/wiki/File:Methoxy_group.svghttp://en.wikipedia.org/wiki/Methoxyhttp://en.wikipedia.org/wiki/Methoxyhttp://en.wikipedia.org/wiki/Ethyl_butyratehttp://en.wikipedia.org/wiki/File:Ethyl_butyrate.pnghttp://en.wikipedia.org/wiki/File:Ester-skeletal.pnghttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Esterhttp://en.wikipedia.org/wiki/Acetic_acidhttp://en.wikipedia.org/wiki/File:Acetic-acid-2D-skeletal.svghttp://en.wikipedia.org/wiki/File:Carboxylic-acid-skeletal.svghttp://en.wikipedia.org/wiki/Carboxylhttp://en.wikipedia.org/wiki/Carboxylic_acidhttp://en.wikipedia.org/wiki/Sodium_acetatehttp://en.wikipedia.org/wiki/File:Sodium-acetate-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Carboxylate-canonical-forms.pnghttp://en.wikipedia.org/wiki/File:Carboxylate-resonance-hybrid.pnghttp://en.wikipedia.org/wiki/Carboxylatehttp://en.wikipedia.org/wiki/Carboxylic_acidhttp://en.wikipedia.org/wiki/Triphosgenehttp://en.wikipedia.org/wiki/File:Carbonate-group.pnghttp://en.wikipedia.org/wiki/Carbonate_esterhttp://en.wikipedia.org/wiki/Carbonate_ester


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Amines

Secondary

amine R2NH amino- -amine Dimethylamine

Tertiary

amineR3N amino- -amine

Trimethylamine

4 ammonium

ionR4N

+ ammonio- -ammonium

Choline

Imine

Primary

ketimineRC(=NH)R' imino- -imine

Secondary

ketimineRC(=NR)R' imino- -imine

Primary

aldimineRC(=NH)H imino- -imine

Ethanimine

Secondary

aldimineRC(=NR')H imino- -imine

Imide Imide (RCO)2NR' imido- -imide

Succinimide

(Pyrrolidine-2,5-dione)

Azide Azide RN3 azido- alkyl azide

Phenyl azide

(Azidobenzene)

Azo

compound

Azo

(Diimide)RN2R' azo- -diazene

Methyl orange

(p-dimethylamino-

azobenzenesulfonic acid)

Cyanates

Cyanate ROCN cyanato- alkyl cyanate

Methyl cyanate

Isocyanate RNCO isocyanato-alkyl

isocyanateMethyl isocyanate

Nitrate Nitrate RONO2nitrooxy-,

nitroxy-alkyl nitrate

Amyl nitrate

(1-nitrooxypentane)

alkanenitrile
http://en.wikipedia.org/wiki/Amyl_nitratehttp://en.wikipedia.org/wiki/File:Amyl_nitrate.svghttp://en.wikipedia.org/wiki/File:Nitrate-group-2D.pnghttp://en.wikipedia.org/wiki/Nitratehttp://en.wikipedia.org/wiki/Nitratehttp://en.wikipedia.org/wiki/Methyl_isocyanatehttp://en.wikipedia.org/wiki/File:Methyl-isocyanate.pnghttp://en.wikipedia.org/wiki/File:Isocyanate-group.pnghttp://en.wikipedia.org/wiki/Isocyanatehttp://en.wikipedia.org/w/index.php?title=Methyl_cyanate&action=edit&redlink=1http://en.wikipedia.org/wiki/File:Methyl_cyanate.pnghttp://en.wikipedia.org/wiki/File:Cyanate-group.pnghttp://en.wikipedia.org/wiki/Cyanatehttp://en.wikipedia.org/wiki/Cyanatehttp://en.wikipedia.org/wiki/Methyl_orangehttp://en.wikipedia.org/wiki/File:Methyl-orange-skeletal.pnghttp://en.wikipedia.org/wiki/File:Azo-group.pnghttp://en.wikipedia.org/wiki/Azo_compoundhttp://en.wikipedia.org/wiki/Azo_compoundhttp://en.wikipedia.org/wiki/Phenyl_azidehttp://en.wikipedia.org/wiki/File:Phenyl_azide-chemical.pnghttp://en.wikipedia.org/wiki/File:Azide-2D.pnghttp://en.wikipedia.org/wiki/Azidehttp://en.wikipedia.org/wiki/Azidehttp://en.wikipedia.org/wiki/Succinimidehttp://en.wikipedia.org/wiki/File:Succinimide.svghttp://en.wikipedia.org/wiki/File:ImideFxnlGp.pnghttp://en.wikipedia.org/wiki/Imidehttp://en.wikipedia.org/wiki/Imidehttp://en.wikipedia.org/wiki/File:Aldimine-(secondary)-skeletal.pnghttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/Ethaniminehttp://en.wikipedia.org/wiki/File:Ethanimine_skeletal.svghttp://en.wikipedia.org/wiki/File:Aldimine-(primary)-skeletal.pnghttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/File:Imine-(secondary)-skeletal.pnghttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/File:Imine-(primary)-skeletal.pnghttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/Iminehttp://en.wikipedia.org/wiki/Cholinehttp://en.wikipedia.org/wiki/File:Choline-skeletal.pnghttp://en.wikipedia.org/wiki/File:Quaternary-ammonium-cation.svghttp://en.wikipedia.org/wiki/Quaternary_ammonium_cationhttp://en.wikipedia.org/wiki/Trimethylaminehttp://en.wikipedia.org/wiki/File:Trimethylamine_chemical_structure.pnghttp://en.wikipedia.org/wiki/File:Amine-(tertiary).pnghttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Dimethylaminehttp://en.wikipedia.org/wiki/File:Dimethylamine-2D.pnghttp://en.wikipedia.org/wiki/File:Amine-(secondary).pnghttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Amine


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NitrileNitrile RCN cyano- alkylcyanide

Benzonitrile

(Phenyl cyanide)

Isonitrile RNC isocyano-alkaneisonitrile

alkyl isocyanide Methyl isocyanide

Nitrite Nitrosooxy RONO nitrosooxy- alkylnitrite Isoamyl nitrite

(3-methyl-1-

nitrosooxybutane)

Nitro

compoundNitro RNO2 nitro-

Nitromethane

Nitroso

compoundNitroso RNO

nitroso-

(Nitrosyl-)

Nitrosobenzene

Pyridine

derivativePyridyl RC5H4N

4-pyridyl

(pyridin-4-yl)

3-pyridyl

(pyridin-3-yl)

2-pyridyl

(pyridin-2-yl)

-pyridine

Nicotine

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.
http://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/File:Nicotine-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:2-pyridyl.pnghttp://en.wikipedia.org/wiki/File:3-pyridyl.pnghttp://en.wikipedia.org/wiki/File:4-pyridyl.pnghttp://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Nitrosobenzenehttp://en.wikipedia.org/wiki/File:Nitrosobenzene.pnghttp://en.wikipedia.org/wiki/File:Nitroso-compound-2D.pnghttp://en.wikipedia.org/wiki/Nitrosohttp://en.wikipedia.org/wiki/Nitrosohttp://en.wikipedia.org/wiki/Nitromethanehttp://en.wikipedia.org/wiki/File:Nitromethane2.pnghttp://en.wikipedia.org/wiki/File:Nitro-group.pnghttp://en.wikipedia.org/wiki/Nitro_functional_grouphttp://en.wikipedia.org/wiki/Nitro_compoundhttp://en.wikipedia.org/wiki/Isoamyl_nitritehttp://en.wikipedia.org/wiki/File:Amyl_nitrite.svghttp://en.wikipedia.org/wiki/File:Nitrite-group-2D.pnghttp://en.wikipedia.org/wiki/Nitritehttp://en.wikipedia.org/wiki/Nitritehttp://en.wikipedia.org/wiki/Methyl_isocyanidehttp://en.wikipedia.org/wiki/File:Methyl_isocyanide.svghttp://en.wikipedia.org/wiki/File:Isocyanide-2D.pnghttp://en.wikipedia.org/wiki/Isonitrilehttp://en.wikipedia.org/wiki/Benzonitrilehttp://en.wikipedia.org/wiki/File:Benzonitrile_structure.pnghttp://en.wikipedia.org/wiki/File:Nitrile-(general)-skeletal.pnghttp://en.wikipedia.org/wiki/Nitrilehttp://en.wikipedia.org/wiki/Nitrile


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Chemical

classGroup Formula

Structural


Thiol Sulfhydryl RSHsulfanyl-

(-SH)-thiol

Ethanethiol

Sulfide

(Thioether)Sulfide RSR'

substituentsulfanyl-

(-SR')di(substituent) sulfide

(Methylsulfanyl)methane (prefix) orDimethyl sulfide (suffix)

Disulfide Disulfide RSSR'substituentdisulfanyl-

(-SSR')di(substituent) disulfide

(Methyldisulfanyl)methane (prefix) or

Dimethyl disulfide (suffix)

Sulfoxide Sulfinyl RSOR'-sulfinyl-

(-SOR')di(substituent) sulfoxide

(Methanesulfinyl)methane (prefix) or

Dimethyl sulfoxide (suffix)

Sulfone Sulfonyl RSO2R'-sulfonyl-

(-SO2R')di(substituent) sulfone

(Methanesulfonyl)methane (prefix) or

Dimethyl sulfone (suffix)

Sulfinic acid Sulfino RSO2Hsulfino-

(-SO2H)-sulfinic acid

2-Aminoethanesulfinic acid

Sulfonic acid Sulfo RSO3Hsulfo-

(-SO3H)-sulfonic acid

Benzenesulfonic acid

Thiocyanate

Thiocyanate RSCNthiocyanato-

(-SCN)substituentthiocyanate

Phenyl thiocyanate

Isothiocyanate RNCSisothiocyanato-

(-NCS)substituentisothiocyanate

Allyl isothiocyanate

Thione Carbonothioyl RCSR'

-thioyl-

(-CSR')

or

sulfanylidene-

(=S)

-thioneDiphenylmethanethione

(Thiobenzophenone)

Thial 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.
http://en.wikipedia.org/wiki/File:Thial.pnghttp://en.wikipedia.org/w/index.php?title=Carbonothioyl&action=edit&redlink=1http://en.wikipedia.org/wiki/Thialhttp://en.wikipedia.org/wiki/Thiobenzophenonehttp://en.wikipedia.org/w/index.php?title=Diphenylmethanethione&action=edit&redlink=1http://en.wikipedia.org/wiki/File:Thiobenzophenone-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Thioketone_structure.pnghttp://en.wikipedia.org/w/index.php?title=Carbonothioyl&action=edit&redlink=1http://en.wikipedia.org/wiki/Thionehttp://en.wikipedia.org/wiki/Allyl_isothiocyanatehttp://en.wikipedia.org/wiki/File:Allyl-isothiocyanate-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Isothiocyanate-group.pnghttp://en.wikipedia.org/wiki/Isothiocyanatehttp://en.wikipedia.org/w/index.php?title=Phenyl_thiocyanate&action=edit&redlink=1http://en.wikipedia.org/wiki/File:Phenyl-thiocyanate-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Thiocyanate-group.pnghttp://en.wikipedia.org/wiki/Thiocyanatehttp://en.wikipedia.org/wiki/Thiocyanatehttp://en.wikipedia.org/wiki/Benzenesulfonic_acidhttp://en.wikipedia.org/wiki/File:Benzenesulfonic-acid-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Sulfonic-acid.pnghttp://en.wikipedia.org/wiki/Sulfonic_acidhttp://en.wikipedia.org/wiki/2-Aminoethanesulfinic_acidhttp://en.wikipedia.org/wiki/File:Hypotaurine.pnghttp://en.wikipedia.org/wiki/File:Sulfinic-acid-2D.pnghttp://en.wikipedia.org/wiki/Sulfinic_acidhttp://en.wikipedia.org/wiki/Dimethyl_sulfonehttp://en.wikipedia.org/w/index.php?title=(Methanesulfonyl)methane&action=edit&redlink=1http://en.wikipedia.org/wiki/File:Dimethylsulfone_Structure.pnghttp://en.wikipedia.org/wiki/File:Sulfone.pnghttp://en.wikipedia.org/wiki/Sulfonehttp://en.wikipedia.org/wiki/Sulfonehttp://en.wikipedia.org/wiki/Dimethyl_sulfoxidehttp://en.wikipedia.org/wiki/(Methanesulfinyl)methanehttp://en.wikipedia.org/wiki/File:Dimethylsulfoxid.svghttp://en.wikipedia.org/wiki/File:Sulfoxide.pnghttp://en.wikipedia.org/wiki/Sulfoxidehttp://en.wikipedia.org/wiki/Sulfoxidehttp://en.wikipedia.org/wiki/Dimethyl_disulfidehttp://en.wikipedia.org/w/index.php?title=(Methyldisulfanyl)methane&action=edit&redlink=1http://en.wikipedia.org/wiki/File:Dimethyl_disulfide.PNGhttp://en.wikipedia.org/wiki/File:Organic_disulfide.pnghttp://en.wikipedia.org/wiki/Disulfidehttp://en.wikipedia.org/wiki/Disulfide_bondhttp://en.wikipedia.org/wiki/Dimethyl_sulfidehttp://en.wikipedia.org/wiki/(Methylsulfanyl)methanehttp://en.wikipedia.org/wiki/File:Dimethylsulfide.pnghttp://en.wikipedia.org/wiki/File:Sulfide-group-2D.pnghttp://en.wikipedia.org/wiki/Sulfidehttp://en.wikipedia.org/wiki/Thioetherhttp://en.wikipedia.org/wiki/Sulfidehttp://en.wikipedia.org/wiki/Ethanethiolhttp://en.wikipedia.org/wiki/File:Ethanethiol-skeletal.pnghttp://en.wikipedia.org/wiki/File:Thiol-group.pnghttp://en.wikipedia.org/wiki/Thiolhttp://en.wikipedia.org/wiki/Thiolhttp://en.wikipedia.org/wiki/Chemical_class


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Chemical

classGroup Formula

Structural


Phosphine

(Phosphane)Phosphino R 3P phosphanyl- -phosphane

Methylpropylphosphane

Phosphonic

acidPhosphono

RP(=O)

(OH)2phosphono-

substituent

phosphonic acidBenzylphosphonic acid

Phosphate PhosphateROP(=O)

(OH)2

phosphonooxy-

or

O-phosphono- (phospho-)

substituent

phosphate

Glyceraldehyde 3-phosphate (suffix)

O-Phosphonocholine (prefix)

(Phosphocholine)

Phosphodiester Phosphate HOPO(OR)2

[(alkoxy)hydroxyphosphoryl]oxy-

or

O-[(alkoxy)hydroxyphosphoryl]-

di(substituent)

hydrogenphosphate

or

phosphoric acid

di(substituent) ester

DNA

O[(2Guanidinoethoxy)hydroxyphosphoryl]Lserine (prefix)

(Lombricine)

Groups containing boron

Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as Lewis acids.

Chemical

classGroup Formula

Structural


Boronic

acidBorono RB(OH)2 Borono- substituentboronic acid

Bortezomib

([(1R)-3-methyl-1-({(2S)-3-phenyl-2-[(pyrazin-2-

ylcarbonyl)amino]propanoyl}amino)butyl]boronic acid)

Boronic

esterBoronate RB(OR)2

O-

[bis(alkoxy)alkylboronyl]-

substituentboronic acid

di(substituent) ester

Borinic

acidBorino R 2BOH Hydroxyborino- di(substituent) borinic acid

Borinic

esterBorinate R2BOR

O-

[alkoxydialkylboronyl]-

di(substituent) borinic acid

substituentester

See also

For a list of all functional groups: Category:Functional groups

Moiety conservation

References

1. ^ Compendium of Chemical Terminology (IUPAC "Gold Book") http://goldbook.iupac.org/F02555.html

2. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.) , New York: Wiley, ISBN 0-471-85472-7

3. ^ IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford

(1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8

doi:10.1351/goldbook.M03968 (http://dx.doi.org/10.1351%2Fgoldbook.M03968) http://goldbook.iupac.org/M03968.html

External links

IUPAC Blue Book (organic nomenclature) (http://www.acdlabs.com/iupac/nomenclature/)

IUPAC ligand abbreviations (http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf) (pdf)_chemical_formula_moiety in CIF dictionary (http://www.iucr.org/__data/iucr/cifdic_html/1/cif_core.dic/Ichemical_formula_moiety.html)

Functional group synthesis (http://www.organic-reaction.com/organic-synthesis/functional-group-synthesis/) from organic-reaction.com

Retrieved from "http://en.wikipedia.org/w/index.php?title=Functional_group&oldid=542040384"

Categories: Functional groups Organic chemistry
http://en.wikipedia.org/wiki/Help:Categorieshttp://en.wikipedia.org/w/index.php?title=Functional_group&oldid=542040384http://www.organic-reaction.com/organic-synthesis/functional-group-synthesis/http://www.iucr.org/__data/iucr/cifdic_html/1/cif_core.dic/Ichemical_formula_moiety.htmlhttp://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdfhttp://www.acdlabs.com/iupac/nomenclature/http://goldbook.iupac.org/M03968.htmlhttp://dx.doi.org/10.1351%2Fgoldbook.M03968http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Special:BookSources/0967855098http://goldbook.iupac.org/http://en.wikipedia.org/wiki/Functional_group#cite_ref-3http://en.wikipedia.org/wiki/Special:BookSources/0-471-85472-7http://en.wikipedia.org/wiki/International_Standard_Book_Numberhttp://en.wikipedia.org/wiki/Jerry_Marchhttp://en.wikipedia.org/wiki/Functional_group#cite_ref-2http://goldbook.iupac.org/F02555.htmlhttp://en.wikipedia.org/wiki/Compendium_of_Chemical_Terminologyhttp://en.wikipedia.org/wiki/Functional_group#cite_ref-1http://en.wikipedia.org/wiki/Moiety_conservationhttp://en.wikipedia.org/wiki/Category:Functional_groupshttp://en.wikipedia.org/wiki/File:Borinate-ester-2D.pnghttp://en.wikipedia.org/wiki/Boronic_acid#Borinic_acids_and_estershttp://en.wikipedia.org/wiki/File:Borinic-acid-2D.pnghttp://en.wikipedia.org/wiki/Boronic_acid#Borinic_acids_and_estershttp://en.wikipedia.org/wiki/File:Boronate-ester-2D.pnghttp://en.wikipedia.org/wiki/Boronic_acid#Boronic_esters_.28also_named_boronate_esters.29http://en.wikipedia.org/wiki/Bortezomibhttp://en.wikipedia.org/wiki/File:Bortezomib.svghttp://en.wikipedia.org/wiki/File:Boronic-acid-2D.pnghttp://en.wikipedia.org/wiki/Boronic_acidhttp://en.wikipedia.org/wiki/Chemical_classhttp://en.wikipedia.org/wiki/Lewis_acidhttp://en.wikipedia.org/wiki/Lombricinehttp://en.wikipedia.org/wiki/DNAhttp://en.wikipedia.org/wiki/File:Phosphodiester-group.pnghttp://en.wikipedia.org/wiki/Phosphatehttp://en.wikipedia.org/wiki/Phosphodiester_bondshttp://en.wikipedia.org/wiki/Phosphocholinehttp://en.wikipedia.org/wiki/File:Phosphocholine.pnghttp://en.wikipedia.org/wiki/Glyceraldehyde_3-phosphatehttp://en.wikipedia.org/wiki/File:G3P-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Phosphate-group.pnghttp://en.wikipedia.org/wiki/Phosphatehttp://en.wikipedia.org/wiki/File:Benzylphosphonic-acid-2D-skeletal.pnghttp://en.wikipedia.org/wiki/File:Phosphonic-acid-generic.pnghttp://en.wikipedia.org/wiki/Phosphonic_acidhttp://en.wikipedia.org/wiki/File:Methylpropylphosphane-skeletal.svghttp://en.wikipedia.org/wiki/File:Phosphine-general.svghttp://en.wikipedia.org/wiki/Phosphanehttp://en.wikipedia.org/wiki/Phosphinehttp://en.wikipedia.org/wiki/Chemical_classhttp://en.wikipedia.org/wiki/Category:Organic_chemistryhttp://en.wikipedia.org/wiki/Category:Functional_groups


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