:Functional group
{{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:
{{legend-line|solid red|Ester group}}
{{legend-line|dashed green|Acetyl group}} {{legend-line|dashed orange|Benzyloxy group}}
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In organic chemistry, a functional group is any 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") [http://goldbook.iupac.org/html/F/F02555.html functional group] {{Webarchive|url=https://web.archive.org/web/20190516163117/http://goldbook.iupac.org/html/F/F02555.html |date=2019-05-16 }}{{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.{{cite book |last= Brown |first= Theodore |title= Chemistry: the central science |publisher= Prentice Hall |location= Upper Saddle River, NJ |year= 2002 |isbn= 0130669970 |page=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 hydrocarbyls 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.
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Chemical class
! Group ! Formula ! Structural Formula ! Prefix ! Suffix ! Example | ||
---|---|---|
Alkane | Alkyl
| R(CH2)nH | File:Alkyl-(general)-skeletal.svg | alkyl- | -ane |
Alkene | Alkenyl
| R2C=CR2 | alkenyl- | -ene
| File:Ethylene.svg |
Alkyne | Alkynyl
| {{chem2|RC\tCR′}} | | alkynyl- | -yne
| |
Benzene derivative
| Phenyl | RC6H5 | phenyl- | -benzene |
There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc. There are several functional groups that contain an alkene such as vinyl group, allyl group, or acrylic group. 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.
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Chemical class
! Group ! Formula ! Structural formula ! Prefix ! Suffix ! Example | ||
---|---|---|
haloalkane | halo
| RX | | halo- | alkyl halide
| 65x65px |
fluoroalkane | fluoro
| RF | | fluoro- | alkyl fluoride
| 92x92px |
chloroalkane | chloro
| RCl | | chloro- | alkyl chloride
| File:Chloromethane.svg |
bromoalkane | bromo
| RBr | | bromo- | alkyl bromide
| 107x107px |
iodoalkane | iodo
| RI | | iodo- | alkyl iodide
| File:Iodomethane.svg |
=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).
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Chemical class
! Group ! Formula ! Structural formula ! Prefix ! Suffix ! Example | ||
---|---|---|
Alcohol | Hydroxyl
| ROH | hydroxy- | -ol |
Ketone | Ketone
| RCOR′ | File:Ketone-group-2D-skeletal.svg | -oyl- (-COR′) | -one
| File:Butanone-skeletal-structure.svg |
Aldehyde | Aldehyde
| RCHO | File:Skeletal formula of an aldehyde group.svg | formyl- (-COH) | -al
| File:Acetaldehyde-skeletal.svg |
Acyl halide | Haloformyl
| RCOX | File:Acyl-halide-skeletal2D.svg | carbonofluoridoyl- | -oyl fluoride -oyl chloride -oyl bromide -oyl iodide | File:Acetyl-chloride.svg |
Carbonate
| ROCOOR′ | File:Carbonate-group-skeletal.svg | (alkoxycarbonyl)oxy- | alkyl carbonate | File:Triphosgen Strukturformel.svg | ||
Carboxylate | RCOO−
| File:Carboxylate-resonance-hybrid.svg | carboxylato- | -oate
| File:Sodium-acetate-2D-skeletal.png |
Carboxylic acid
| Carboxyl | RCOOH
| File:Carboxylic-acid-skeletal.svg | carboxy- | -oic acid
| File:Acetic-acid-2D-skeletal.svg |
Ester | Carboalkoxy
| RCOOR′ | alkanoyloxy- | alkyl alkanoate | File:Ethyl butyrate.png | |
Hydroperoxide
| ROOH | File:Hydroperoxide-group-2D.svg | hydroperoxy- | alkyl hydroperoxide | ||
Peroxide
| Peroxy | ROOR′ | peroxy- | alkyl peroxide | ||
Ether | Ether
| ROR′ | alkoxy- | alkyl ether | File:Diethyl ether chemical structure.svg | |
Hemiacetal | Hemiacetal
| R2CH(OR1)(OH) | alkoxy -ol | -al alkyl hemiacetal | | |
Hemiketal | Hemiketal
| RC(ORʺ)(OH)R′ | File:Hemiketal-2D-skeletal.png | alkoxy -ol | -one alkyl hemiketal | | |
Acetal | Acetal
| RCH(OR′)(OR″) | dialkoxy- | -al dialkyl acetal | | |
Ketal (or Acetal) | Ketal (or Acetal)
| {{nowrap|RC(OR″)(OR‴)R′}} | dialkoxy- | -one dialkyl ketal | | |
Orthoester | Orthoester
| {{nowrap|RC(OR′)(OR″)(OR‴)}} | File:Orthoester general structure.svg | trialkoxy- | | | |
Heterocycle (if cyclic) | Methylenedioxy
| {{nowrap|(–OCH2O–)}} | File:Methylenedioxy graphic (ChemDraw).png | methylenedioxy- | -dioxole | 75px | |
Orthocarbonate ester | Orthocarbonate ester
| {{nowrap|C(OR)(OR′)(OR″)(OR‴)}} | File:Orthocarbonate-ester.svg | tetralkoxy- | tetraalkyl orthocarbonate | |
Organic acid anhydride | Carboxylic anhydride
| {{nowrap|R1(CO)O(CO)R2}} | File:FunktionelleGruppen Carbonsäureanhydrid.svg | | anhydride |
=Groups containing nitrogen=
Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.
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Chemical class
! Group ! Formula ! Structural formula ! Prefix ! Suffix ! Example | ||
---|---|---|
Amide | Carboxamide
| RCONR'R" | File:Amide-(tertiary)-skeletal.svg | carboxamido- | -amide
| File:Acetamide skeletal.svg |
Amidine
|R4C(NR1)(NR2R3) | amidino- | -amidine |File:Acetamidine-2D-skeletal.pngacetamidine (acetimidamide) | ||
Guanidine
|RNC(NR2)2) |File:Guanidine-group-2D-skeletal.svg | Guanidin- | -Guanidine |File:Guanidinopropionic acid.pngGuanidinopropionic acid | ||
rowspan="5" | Amines
| RNH2 | amino- | -amine
| File:Methylamine-2D.png | |
Secondary amine
| R'R"NH | amino- | -amine | |
Tertiary amine
| R3N | amino- | -amine | |
4° ammonium ion
| R4N+ | File:Quaternary-ammonium-cation.svg | ammonio- | -ammonium | |
Hydrazone
|R'R"CN2H2 |hydrazino- | -hydrazine | ||
rowspan="4" | Imine
| RC(=NH)R' | File:Imine-(primary)-skeletal.svg | imino- | -imine
| | |
Secondary ketimine
| | File:Imine-(secondary)-skeletal.svg | imino- | -imine
| | |
Primary aldimine
| RC(=NH)H | File:Aldimine-(primary)-skeletal.svg | imino- | -imine | |
Secondary aldimine
| RC(=NR')H | File:Aldimine-(secondary)-skeletal.svg | imino- | -imine
| | |
Imide | Imide
| (RCO)2NR' | imido- | -imide | File:Succinimide.svg | |
Azide
| Azide | RN3 | azido- | alkyl azide
| File:Phenyl azide-chemical.png | |
Azo compound
| RN2R' | azo- | -diazene
| File:Methyl-orange-skeletal.png | |
rowspan=2|Cyanates
| Cyanate | ROCN
| cyanato- | alkyl cyanate |File:Methyl cyanate.svg | |
Isocyanate | RNCO
| isocyanato- | alkyl isocyanate | |
Nitrate | Nitrate
| RONO2 | nitrooxy-, nitroxy- | alkyl nitrate
| File:Amyl nitrate.svg |
rowspan=2|Nitrile
| Nitrile | RCN | | cyano- | alkanenitrile | File:Benzonitrile structure.png | ||
Isonitrile | RNC
| File:Isonitrile structural formula.svg | isocyano- | alkaneisonitrile | |
Nitrite | Nitrosooxy
| RONO | nitrosooxy- | alkyl nitrite
| File:Amyl nitrite.svg |
Nitro compound
| Nitro | RNO2 | nitro- | ||
Nitroso compound
| Nitroso | RNO
| File:Nitroso-compound-2D.svg | nitroso- (Nitrosyl-) | |
Oxime
| Oxime | RCH=NOH
| File:General structure of oximes.svg | | Oxime
| File:acetoxime.svg |
Pyridine derivative
| Pyridyl | RC5H4N | | 4-pyridyl 3-pyridyl 2-pyridyl | -pyridine | ||
Carbamate ester | RO(C=O)NR2
| File:Carbamate-group-2D-skeletal.png | (-carbamoyl)oxy- | -carbamate
| File:Isopropyl (3-chlorophenyl)carbamate 200.svg |
=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.
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Chemical class
! Group ! Formula ! Structural formula ! Prefix ! Suffix ! Example | |
---|---|
Thiol
| RSH | sulfanyl- | -thiol | |
Sulfide (Thioether) | Sulfide | RSR' | substituent sulfanyl- | di(substituent) sulfide | | |
Disulfide | Disulfide
| RSSR' | File:Disulfide general formula.svg | substituent disulfanyl- | di(substituent) disulfide | |
Sulfoxide
| Sulfinyl | RSOR' | -sulfinyl- | di(substituent) sulfoxide | File:Dimethylsulfoxid.svg | |
Sulfone
| Sulfonyl | RSO2R' | -sulfonyl- | di(substituent) sulfone | File:DMSO2.svg | |
Sulfinic acid | Sulfino
| RSO2H | 75px | sulfino- | -sulfinic acid |
Sulfonic acid | Sulfo
| RSO3H | sulfo- | -sulfonic acid | File:Benzenesulfonic-acid-2D-skeletal.png |
Sulfonate ester | Sulfo
| RSO3R' | (-sulfonyl)oxy- | R R-sulfonate' | File:StructureMeOTf.svg |
rowspan=2|Thiocyanate | RSCN
| thiocyanato- | substituent thiocyanate |
Isothiocyanate | RNCS
| File:Isothiocyanate-group.svg | isothiocyanato- | substituent isothiocyanate | File:Allyl-isothiocyanate-2D-skeletal.png |
Thioketone
| RCSR' | File:Thioketone-skeletal.svg | -thioyl- | -thione | File:Thiobenzophenone-2D-skeletal.png | |
Thial
| RCSH | methanethioyl- | -thial | | |
rowspan=2| Thiocarboxylic acid
| Carbothioic S-acid | RC=OSH | mercaptocarbonyl- | -thioic S-acid | File:Thiobenzoic acid.svg | |
Carbothioic O-acid
| RC=SOH | hydroxy(thiocarbonyl)- | -thioic O-acid | | |
rowspan=2| Thioester
| Thiolester | RC=OSR' | File:Thiolester-skeletal.svg | | S-alkyl-alkane-thioate | File:S-methyl-thioacrylate-2D-skeletal.png | |
Thionoester
| RC=SOR' | File:Thionoester-skeletal.svg | | O-alkyl-alkane-thioate | | |
Dithiocarboxylic acid
| Carbodithioic acid | RCS2H | File:Dithioic-acid-skeletal.svg | dithiocarboxy- | -dithioic acid | File:PhCS2H.svg | |
Dithiocarboxylic acid ester
| Carbodithio | RC=SSR' | File:Dithioic-acid-ester-skeletal.svg | | -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.
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Chemical class
! Group ! Formula ! Structural formula ! Prefix ! Suffix ! Example | ||
---|---|---|
Phosphine (Phosphane) | Phosphino
| R3P | phosphanyl- | -phosphane
| File:Methylpropylphosphane-skeletal.svg |
Phosphonic acid
| Phosphono | | phosphono- | substituent phosphonic acid | File:Benzylphosphonic-acid-2D-skeletal.png | ||
rowspan=2| Phosphate
| rowspan=2| Phosphate | rowspan=2| | rowspan=2| File:Phosphate-group.svg | rowspan=2| phosphonooxy- | rowspan=2| substituent phosphate | File:G3P-2D-skeletal.png | ||
File:Phosphocholine.png O-Phosphonocholine (prefix) (Phosphocholine) | ||
rowspan=2|Phosphodiester
| rowspan=2|Phosphate | rowspan=2|HOPO(OR)2 | rowspan=2|File:Phosphodiester-group.svg | rowspan=2|[(alkoxy)hydroxyphosphoryl]oxy- | rowspan=2|di(substituent) hydrogen phosphate | 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.
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Chemical class | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Boronic acid | Borono | RB(OH)2 | File:Boronic-acid-2D.svg | Borono- | substituent boronic acid | {{center|File:Phenylboronic acid.png Phenylboronic acid}} |
Boronic ester | Boronate | RB(OR)2 | File:Boronate-ester-2D.svg | O-[bis(alkoxy)alkylboronyl]- | substituent boronic acid di(substituent) ester | |
Borinic acid | Borino | R2BOH | File:Borinic-acid-2D.svg | Hydroxyborino- | di(substituent) borinic acid | |
Borinic ester | Borinate | R2BOR | File:Borinate-ester-2D.svg | O-[alkoxydialkylboronyl]- | di(substituent) borinic acid substituent ester | {{center|File:2-APB.png Diphenylborinic acid 2-aminoethyl ester (2-Aminoethoxydiphenyl borate)}} |
= Groups containing metals =
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|+ !Chemical class !Structural formula !Prefix !Suffix !Example |
Alkyllithium
|RLi | rowspan="4" |(tri/di)alkyl- | -lithium |
Alkylmagnesium halide
|RMgX (X=Cl, Br, I){{Ref label|halogen|note 1|note 1}} | -magnesium halide |
Alkylaluminium
|Al2R6 | -aluminium |
Silyl ether
|R3SiOR | -silyl ether |
{{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 methylidene 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),{{cite web|url=https://www.acdlabs.com/iupac/nomenclature/93/r93_271.htm|title=R-2. 5 Substituent Prefix Names Derived from Parent Hydrides|publisher=IUPAC|year=1993|access-date=2018-12-15|archive-date=2019-03-22|archive-url=https://web.archive.org/web/20190322061930/https://www.acdlabs.com/iupac/nomenclature/93/r93_271.htm|url-status=live}} section P-56.2.1 carbyne for methylidyne, and trityl for triphenylmethyl.
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Chemical class | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Single bond | R• | Ylo-{{cite web|url=http://www.chem.qmul.ac.uk/iupac/ions/RC813.html|title=Revised Nomenclature for Radicals, Ions, Radical Ions and Related Species (IUPAC Recommendations 1993: RC-81.3. Multiple radical centers)|access-date=2014-12-02|archive-url=https://web.archive.org/web/20170611171918/http://www.chem.qmul.ac.uk/iupac/ions/RC813.html|archive-date=2017-06-11|url-status=dead}} | -yl | {{center|Methyl group Methyl radical}} | ||
Double bond | R: | ? | -ylidene | {{center|Methylidene}} | ||
Triple bond | R⫶ | ? | -ylidyne | {{center|Methylidyne}} | ||
Carboxylic acyl radical | Acyl | R−C(=O)• | ? | -oyl | {{center|Acetyl}} |
See also
References
{{Reflist|refs=
{{cite web |url=http://www.chem.qmul.ac.uk/iupac/ions/RC811.html#p11|title=RC-81.1.1. Monovalent radical centers in saturated acyclic and monocyclic hydrocarbons, and the mononuclear EH4 parent hydrides of the carbon family |last=Moss |first=G. P. |author2=W.H. Powell |work=IUPAC Recommendations 1993 |publisher=Department of Chemistry, Queen Mary University of London|access-date=25 February 2015 |archive-url=https://web.archive.org/web/20150209155729/http://www.chem.qmul.ac.uk/iupac/ions/RC811.html|archive-date=9 February 2015}}
}}
External links
{{Commons|Functional groups}}
- [https://www.acdlabs.com/iupac/nomenclature/ IUPAC Blue Book (organic nomenclature)]
- {{cite web|url=http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf|title=IUPAC ligand abbreviations|date=2 April 2004|publisher=IUPAC|access-date=25 February 2015 |archive-url= https://web.archive.org/web/20070927121055/http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf |archive-date=27 September 2007}}
- [https://www.pearson.com/channels/organic-chemistry/learn/johnny/molecular-representations/functional-groups Functional group video]
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