Functional group 10911 224881786 2008-07-10T20:46:19Z VolkovBot 3035831 robot Adding: [[uk:Функціональна група]] {{otheruses}} [[Image:FG-vs-moiety.png|thumb|150px|[[Benzyl acetate]] has an ester functional group (in red), an acetyl moiety (circled with green) and an benzyl alcohol moiety (circled with orange).]] In [[organic chemistry]], '''functional groups''' are specific groups of [[atom]]s within [[molecule]]s that are responsible for the characteristic [[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.<ref>[[Compendium of Chemical Terminology]] (IUPAC "Gold Book") http://goldbook.iupac.org/F02555.html</ref><ref>{{JerryMarch}}</ref> However, its relative reactivity can be modified by nearby functional groups. The word '''[[moiety]]''' is often used synonymously to "functional group", but according to the IUPAC definition, a moiety is a half of a molecule including substructures of functional groups. For example, an [[ester]] is divided into an alcohol and an acyl moiety, but has an ester functional group. The use of the word "moiety" to mean a functional group in the chemistry sense is actually fairly recent. While it has commonly been used in the archeology field to mean the half of a tribal family, it wasn't until a chance encounter between Elizabeth Bollwerk, an archeology graduate student, and a drug research scientist that the term made the cross-over.<ref>Schleselmann, L. (2004), Pharmacy Times, "Pharmacological History Notes", http://www.pharmacytimes.com/issues/articles/2004-06_121.asp accessed 5/1/08</ref> Combining the names of functional groups with the names of the parent [[alkane]]s generates a powerful [[systematic name|systematic nomenclature]] for naming [[organic compound]]s. The non-hydrogen atoms of functional groups are always associated with each other and with the rest of the molecule by [[covalent bond]]s. When the group of atoms is associated with the rest of the molecule primarily by ionic forces, the group is referred to more properly as a [[polyatomic ion]] or [[complex ion]]. And all of these are called [[radical (chemistry)|radical]]s, by a meaning of the term ''radical'' that predates the [[free radical]]. 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. Functional groups are attached to the carbon backbone of organic molecules. They determine the characteristics and chemical reactivity of molecules. Functional groups are far less stable than the carbon backbone and are likely to participate in chemical reactions. = 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 that vary based upon the number and order of π bonds impart different chemistry. Each listing below contains C-H bonds, but each one differs in type (and scope) of reactivity. {| class="wikitable" style="background: #ffffff; text-align: center;width:800px" |- ! [[Chemical class]] ! Group ! Formula ! Structural Formula ! Prefix ! Suffix ! Example |- | [[Alkane]] || [[Alkyl]] | RH | [[Image:Alkyl-(general)-skeletal.svg|75px|Alkyl]] | alkyl- || -ane | [[Image:Ethane-2D.png|75px|methane]]<br>[[Ethane]] |- | [[Alkene]] || [[Alkene|Alkenyl]] | R<sub>2</sub>C=CR<sub>2</sub> | [[Image:Alkene-(general)-skeletal.png|75px|Alkene]] | alkenyl- || -ene | [[Image:Ethylene.svg|75px|ethylene]]<br>[[Ethylene]]<br/>''(Ethene)'' |- | [[Alkyne]] || [[Alkyne|Alkynyl]] | RC≡CR' | [[Image:Alkyne-(general)-skeletal.png|100px|Alkyne]] | alkynyl- || -yne | [[Image:Acetylene-2D.png|100px|acetylene]]<br>[[Acetylene]]<br/>''(Ethyne)'' |- |- | [[Benzene|Benzene derivative]] | [[Phenyl]] | RC<sub>6</sub>H<sub>5</sub><br />RPh | [[Image:Phenyl-group.png|75px|Phenyl]] | phenyl- || -benzene | [[Image:Cumene-2D-skeletal.png|75px|Cumene]]<br />[[Cumene]]<br/>''(2-phenylpropane)'' |- | [[Toluene|Toluene derivative]] | [[Benzyl]] | RCH<sub>2</sub>C<sub>6</sub>H<sub>5</sub><br />RBn | [[Image:Benzyl-group.png|75px|Benzyl]] | benzyl- | 1-(''substituent'')toluene | [[Image:Benzyl-bromide-skeletal.svg|75px|Benzyl bromide]]<br />[[Benzyl bromide]]<br />''(1-Bromotoluene)'' |- |} There are also a large number of branched or ring alkanes that have specific names, e.g. [[tert-butyl]], [[bornyl]], [[cyclohexyl]], etc. == 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 reaction]]s. 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:800px" |- ! [[Chemical class]] ! Group ! Formula ! Structural Formula ! Prefix ! Suffix ! Example |- | [[haloalkane]] || [[halogen|halo]] | RX | [[Image:Halide-group.png|50px|Halide group]] | halo- || alkyl '''halide''' | [[Image:Chloroethane-skeletal.png|75px|Chloroethane]]<br>[[Chloroethane]]<br>''(Ethyl chloride)'' |- | [[fluoroalkane]] || [[fluorine|fluoro]] | RF | [[Image:Fluoro-group.png|50px|Fluoro group]] | fluoro- || alkyl '''fluoride''' | [[Image:Fluoromethane-2D.png|75px|Fluoromethane]]<br>[[Fluoromethane]]<br>''(Methyl fluoride)'' |- | [[chloroalkane]] || [[chlorine|chloro]] | RCl | [[Image:Chloro-group.png|50px|Chloro group]] | chloro- || alkyl '''chloride''' | [[Image:Chloromethane.svg|75px|Chloromethane]]<br>[[Chloromethane]]<br>''(Methyl chloride)'' |- | [[bromoalkane]] || [[bromine|bromo]] | RBr | [[Image:Bromo-group.png|50px|Bromo group]] | bromo- || alkyl '''bromide''' | [[Image:Bromomethane-2D.png|75px|Bromomethane]]<br>[[Bromomethane]]<br>''(Methyl bromide)'' |- | [[iodoalkane]] || [[iodine|iodo]] | RI | [[Image:Iodo-group.png|50px|Iodo group]] | iodo- || alkyl '''iodide''' | [[Image:Iodomethane.svg|75px|Iodomethane]]<br>[[Iodomethane]]<br>''(Methyl iodide)'' |- |} == Groups containing oxygen == Compounds that contain C-O bonds each possess differing reactivity based upon the location and [[orbital hybridisation|hybridization]] of the C-O bond, owing to the electron-withdrawing effect of sp² hybridized oxygen and the donating effects of sp³ hybridized oxygen. {| class="wikitable" style="background: #ffffff; text-align: center;width:800px" |- ! [[Chemical class]] ! Group ! Formula ! Structural Formula ! Prefix ! Suffix ! Example |- | [[Acyl halide]] || Haloformyl | RCOX | [[Image:Acyl-halide-skeletal.png|75px|Acyl halide]] | haloformyl- || -oyl halide | [[Image:Acetyl-chloride.png|75px|Acetyl chloride]]<br />[[Acetyl chloride]]<br/>''(Ethanoyl chloride)'' |- | [[Alcohol]] || [[Hydroxyl]] | ROH | [[Image:Alcohol-(general)-skeletal.png|75px|Hydroxyl]] | hydroxy- || -ol | [[Image:Methanol-2D.png|90px|methanol]]<br>[[Methanol]] |- | [[Ketone]] || [[Carbonyl]] | RCOR' | [[Image:Ketone-skeletal.png|Ketone|75px]] | keto-, oxo- || -one | [[Image:Butanone-structure-skeletal.png|75px|Butanone]]<br />[[Methyl ethyl ketone]]<br>''(Butanone)'' |- | [[Aldehyde]] || [[Aldehyde]] | RCHO | [[Image:Aldehyde-skeletal.png|75px|Aldehyde]] | aldo- || -al | [[Image:Acetaldehyde-skeletal.svg|75px|acetaldehyde]]<br>[[Acetaldehyde]]<br/>''(Ethanal)'' |- |[[Carbonate ester|Carbonate]] | [[Carbonate ester]] | ROCOOR | [[Image:Carbonate-group.png|75px|Carbonate]] | | alkyl '''carbonate''' | |- | [[Carboxylic acid|Carboxylate]] | [[Carboxylate]] || RCOO<sup>−</sup> | [[Image:Carboxylate-resonance-hybrid.png|75px|Carboxylate]]<br> [[Image:Carboxylate-canonical-forms.png|75px|Carboxylate]] | carboxy- || -oate | [[Image:Sodium-acetate-2D-skeletal.png|75px|Sodium acetate]]<br />[[Sodium acetate]]<br />''(Sodium ethanoate)'' |- | [[Carboxylic acid]] | [[Carboxyl]] || RCOOH | [[Image:Carboxylic-acid-skeletal.svg|75px|Carboxylic acid]] | carboxy- || -oic acid | [[Image:Acetic-acid-2D-skeletal.png|75px|Acetic acid]]<br />[[Acetic acid]]<br />''(Ethanoic acid)'' |- | [[Ether]] || [[Ether]] | ROR' | [[Image:Ether-(general).png|75px|Ether]] | alkoxy- | alkyl alkyl '''ether''' | [[Image:Diethyl-ether-2D-skeletal.png|75px|Diethyl ether]]<br>[[Diethyl ether]]<br>''(Ethoxyethane)'' |- | [[Ester]] || [[Ester]] | RCOOR' | [[Image:Ester-skeletal.png|Ester|75px]] | || alkyl alkan'''oate''' | [[Image:Ethyl butyrate.png|75px|Ethyl butyrate]]<br>[[Ethyl butyrate]]<br>''(Ethyl butanoate)'' |- | [[Organic peroxide|Hydroperoxide]] | [[Organic peroxide|Hydroperoxy]] | ROOH | [[Image:Hydroperoxide-group-2D.png|75px|Hydroperoxy]] | hydroperoxy- | alkyl '''hydroperoxide''' | [[Image:Methyl-ethyl-ketone-peroxide-2D-skeletal.png|75px|Methyl ethyl ketone peroxide]]<br />[[Methyl ethyl ketone peroxide]] |- | [[Organic peroxide|Peroxide]] | [[Organic peroxide|Peroxy]] | ROOR | [[Image:Peroxy-group.png|75px|Peroxy]] | peroxy- | alkyl '''peroxide''' | [[Image:DTBP.png|75px|Di-tert-butyl peroxide]]<br />[[Di-tert-butyl peroxide]] |- |} == 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:800px" |- ! [[Chemical class]] ! Group ! Formula ! Structural Formula ! Prefix ! Suffix ! Example |- | [[Amide]] || [[Carboxamide]] | RCONR<sub>2</sub> | [[Image:Amide-(tertiary)-skeletal.png|75px|Amide]] | carboxamido- || -amide | [[Image:Acetamide structure.png|75px|acetamide]]<br>[[Acetamide]]<br/>''(Ethanamide)'' |- | rowspan="4" | [[Amine]]s | [[amine|Primary amine]] | RNH<sub>2</sub> | [[Image:1°-amino-group.png|75px|Primary amine]] | amino- || -amine | [[Image:Methylamine-2D.png|75px|methylamine]]<br>[[Methylamine]]<br/>''(Methanamine)'' |- | [[amine|Secondary amine]] | R<sub>2</sub>NH | [[Image:Amine-(secondary).png|75px|Secondary amine]] | amino- || -amine | [[Image:Dimethylamine-2D.png|75px|dimethylamine]]<br>[[Dimethylamine]] |- | [[amine|Tertiary amine]] | R<sub>3</sub>N | [[Image:Amine-(tertiary).png|75px|Tertiary amine]] | amino- || -amine | [[Image:Trimethylamine chemical structure.png|75px|trimethylamine]]<br>[[Trimethylamine]] |- | [[Quaternary ammonium cation|4° ammonium ion]] | R<sub>4</sub>N<sup>+</sup> | [[Image:Quaternary-ammonium-cation.svg|75px|Quaternary ammonium cation]] | ammonio- || -ammonium | [[Image:Choline-skeletal.png|150px|choline]]<br>[[Choline]] |- |rowspan="4" | [[Imine]] | [[imine|Primary ketimine]] | RC(=NH)R' | [[Image:Imine-(primary)-skeletal.png|75px|Imine]] | imino- || -imine | |- | [[imine|Secondary ketimine]] | RC(=NR'')R' | [[Image:Imine-(secondary)-skeletal.png|75px|Imine]] | imino- || -imine | |- | [[imine|Primary aldimine]] | RC(=NH)H | [[Image:Aldimine-(primary)-skeletal.png|75px|Imine]] | imino- || -imine | |- | [[imine|Secondary aldimine]] | RC(=NR')H | [[Image:Aldimine-(secondary)-skeletal.png|75px|Imine]] | imino- || -imine | |- | [[Imide]] || [[Imide]] | RC(=O)NC(=O)R' | [[Image:Imide.png|75px|Imide]] | imido- | -imide |- | [[Azide]] | [[Azide]] | RN<sub>3</sub> | [[Image:Azide-2D.png|75px|Organoazide]] | azido- || alkyl '''azide''' | [[Image:Phenyl azide-chemical.png|75px|Phenyl azide]]<br/>[[Phenyl azide]]<br/>(Azidobenzene) |- | [[Azo compound]] | [[Azo compound|Azo<br />(Diimide)]] | RN<sub>2</sub>R' | [[Image:Azo-group.png|75px|Azo.pngl]] | azo- || -diazene | [[Image:Methyl-orange-skeletal.png|150px|Methyl orange]]<br/>[[Methyl orange]]<br/>(p-dimethylamino-azobenzenesulfonic acid) |- | rowspan="2" | [[Cyanate]]s | [[Cyanate]] || ROCN | [[Image:Cyanate-group.png|75px|Cyanate]] | cyanato- | alkyl '''cyanate''' | |- | [[Isocyanide]] || RNC | [[Image:Isocyanide-2D.png|75px|Isocyanide]] | isocyano- | alkyl '''isocyanide''' | |- | rowspan="2" | [[Isocyanate]]s | [[Isocyanate]] || RNCO | [[Image:Isocyanate-group.png|75px|Isocyanate]] | isocyanato- | alkyl '''isocyanate''' | [[Image:Methyl-isocyanate.png|100px|Methyl isocyanate]]<br />[[Methyl isocyanate]] |- | [[Isothiocyanate]] || RNCS | [[Image:Isothiocyanate-group.png|75px|Isothiocyanate]] | isothiocyanato- | alkyl '''isothiocyanate''' | [[Image:Allyl-isothiocyanate-2D-skeletal.png|100px|Allyl isothiocyanate]]<br />[[Allyl isothiocyanate]] |- | [[Nitrate]] || [[Nitrate]] | RONO<sub>2</sub> | [[Image:Nitrate-group-2D.png|75px|Nitrate]] | nitrooxy-, nitroxy- || alkyl '''nitrate''' | [[Image:Amyl-nitrate-2D-skeletal.png|150px|Amyl nitrate]]<br/>[[Amyl nitrate]]<br>''(1-nitrooxypentane)'' |- | [[Nitrile]] || [[Nitrile]] | RCN | [[Image:Nitrile-(general)-skeletal.png|75px|Nitrile]] | cyano- || alkane'''nitrile'''<br> alkyl '''cyanide''' | [[Image:Benzonitrile structure.png|75px|Benzonitrile]]<br />[[Benzonitrile]]<br>''(Phenyl cyanide)'' |- | [[Nitrite]] || [[Nitrite|Nitrosooxy]] | RONO | [[Image:Nitrite-group-2D.png|75px|Nitrite]] | nitrosooxy- || alkyl '''nitrite''' | [[Image:Amyl nitrite.svg|150px|Amyl nitrite]]<br/>[[Isoamyl nitrite]]<br>''(3-methyl-1-nitrosooxybutane)'' |- | [[Nitro compound]] | [[Nitro functional group|Nitro]] | RNO<sub>2</sub> | [[Image:Nitro-group.png|75px|Nitro]] | nitro- || &nbsp; | [[Image:Nitromethane2.png|75px|Nitromethane]]<br />[[Nitromethane]] |- | [[Nitroso|Nitroso compound]] | [[Nitroso]] || RNO | [[Image:Nitroso-compound-2D.png|75px|Nitroso]] | nitroso- || &nbsp; | [[Image:Nitrosobenzene.png|75px|Nitrosobenzene]]<br />[[Nitrosobenzene]] |- | [[Pyridine|Pyridine derivative]] | [[Pyridine|Pyridyl]] | RC<sub>5</sub>H<sub>4</sub>N | [[Image:4-pyridyl.png|75px|4-pyridyl group]]<br> [[Image:3-pyridyl.png|75px|3-pyridyl group]]<br> [[Image:2-pyridyl.png|75px|2-pyridyl group]]<br> | 4-pyridyl<br>(pyridin-4-yl) 3-pyridyl<br>(pyridin-3-yl) 2-pyridyl<br>(pyridin-2-yl) | -pyridine | [[Image:Nicotine-2D-skeletal.png|75px|Nicotine]]<br />[[Nicotine]] |- |} ==Groups containing phosphorus and sulfur == Compounds that contain sulfur and phosphorus exhibit unique chemistry due to their ability to form more bonds than nitrogen and oxygen, 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]] || Phosphino | R<sub>3</sub>P | [[Image:Phosphine-general.svg|75px|A tertiary phosphine]] | phosphino- || -phosphane | [[Image:Methylpropylphosphane-skeletal.svg|75px|Methylpropylphosphane]]<br />Methylpropylphosphane |- | [[Phosphodiester bonds|Phosphodiester]] | [[Phosphate]] | HOPO(OR)<sub>2</sub> | [[Image:Phosphodiester-group.png|75px|Phosphodiester]] | phosphoric acid di(''substituent'') ester | di(''substituent'') hydrogenphosphate | [[DNA]] |- | [[Phosphonic acid]] || Phosphono | RP(=O)(OH)<sub>2</sub> | [[Image:Phosphonic-acid-generic.png|75px|Phosphono group]] | phosphono- | ''substituent'' phosphonic acid | [[Image:Benzylphosphonic-acid-2D-skeletal.png|75px|Benzylphosphonic acid]]<br />Benzylphosphonic acid |- | [[Phosphate]] || Phosphate | ROP(=O)(OH)<sub>2</sub> | [[Image:Phosphate-group.png|75px|Phosphate group]] | phospho- || | [[Image:G3P-2D-skeletal.png|75px|Glyceraldehyde 3-phosphate]]<br />[[Glyceraldehyde 3-phosphate]] |- | [[Sulfide]] or [[thioether]] | | RSR' | [[Image:Sulfide-group-2D.png|75px|Sulfide group]] | | di(''substituent'') sulfide | [[Image:Dimethylsulfide.png|75px|Dimethyl sulfide]]<br />[[Dimethyl sulfide]] |- | [[Sulfone]] | [[Sulfone|Sulfonyl]] | RSO<sub>2</sub>R' | [[Image:Sulfone.png|75px|Sulfonyl group]] | sulfonyl- | di(''substituent'') sulfone | [[Image:Dimethylsulfone Structure.png|75px|Dimethyl sulfone]]<br />Dimethyl sulfone<br>''([[Methylsulfonylmethane]])'' |- | [[Sulfonic acid]] || Sulfo | RSO<sub>3</sub>H | [[Image:Sulfonic-acid.png|75px|Sulfonyl group]] | sulfo- | ''substituent'' '''sulfonic acid''' | [[Image:Benzenesulfonic-acid-2D-skeletal.png|75px|Benzenesulfonic acid]]<br />Benzenesulfonic acid |- | [[Sulfoxide]] | [[Sulfoxide|Sulfinyl]] | RSOR' | [[Image:Sulfoxide.png|75px|Sulfinyl group]] | sulfinyl- | di(''substituent'') '''sulfoxide''' | [[Image:Diphenyl-sulfoxide.png|75px|Diphenyl sulfoxide]]<br />Diphenyl sulfoxide |- | [[Thiol]] | [[Thiol|Sulfhydryl]] | RSH | [[Image:Thiol-group.png|75px|Sulfhydryl]] | mercapto-, sulfanyl- | -thiol | [[Image:Ethanethiol-skeletal.png|75px|Ethanethiol]]<br />[[Ethanethiol]]<br />''(Ethyl mercaptan)'' |- | [[Thiocyanate]] | [[Thiocyanate]] || RSCN | [[Image:Thiocyanate-group.png|75px|Thiocyanate]] | thiocyanato- | alkyl '''thiocyanate''' | |- | [[Disulfide bond|Disulfide]] || [[Disulfide]] | RSSR' | [[Image:Organic disulfide.png|75px|Disulfide]] | | alkyl alkyl disulfide | [[Image:Diphenyl disulfide.png|130px|Diphenyl disulfide]]<br>[[Diphenyl disulfide]]<br>''1,2-diphenyldisulfane'' |- |} == Other == * For a list of all functional groups: [[:Category:Functional groups]] ==References== {{Reflist}} ==External links== * [http://www.acdlabs.com/iupac/nomenclature/ IUPAC Blue Book (organic nomenclature)] * [http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf IUPAC ligand abbreviations] (pdf) * [http://www.aceorganicchem.com/organic_chemistry_flash_cards.htm Organic Chemistry Help: Functional Groups Flashcards] {{Functional Groups}} {{Organic chemistry}} [[Category:Functional groups| ]] [[Category:Organic compounds]] [[ar:مجموعة وظيفية]] [[bs:Funkcionalna grupa]] [[ca:Grup funcional]] [[cs:Funkční skupina]] [[da:Funktionel gruppe]] [[de:Funktionelle Gruppe]] [[et:Funktsionaalrühm]] [[el:Χαρακτηριστική ομάδα]] [[es:Grupo funcional]] [[eo:Funkcia grupo]] [[fa:گروه عاملی]] [[fr:Groupe fonctionnel]] [[ko:작용기]] [[id:Gugus fungsional]] [[it:Gruppo funzionale]] [[he:קבוצה פונקציונלית]] [[mk:Функционална група]] [[ms:Kumpulan berfungsi]] [[nl:Functionele groep]] [[ja:基]] [[no:Liste over funksjonelle grupper]] [[nn:Funksjonell gruppe]] [[oc:Grop foncional]] [[pl:Grupa funkcyjna]] [[pt:Funções orgânicas]] [[ro:Grupă funcţională]] [[ru:Функциональная группа]] [[sk:Funkčná skupina]] [[fi:Funktionaalinen ryhmä]] [[sv:Funktionell grupp]] [[th:หมู่ฟังก์ชัน]] [[vi:Nhóm chức]] [[tr:Fonksiyonel grup]] [[uk:Функціональна група]] [[zh:官能团]]