: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}}

]]

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.

class="wikitable" style="background: #ffffff; text-align: center;width:550px"
Chemical class

! Group

! Formula

! Structural Formula

! Prefix

! Suffix

! Example

AlkaneAlkyl

| R(CH2)nH

| File:Alkyl-(general)-skeletal.svg

| alkyl-

-ane

| 135x135px
Ethane

AlkeneAlkenyl

| R2C=CR2

| File:Alkene-2D-skeletal.svg

| alkenyl-

-ene

| File:Ethylene.svg
Ethylene
(Ethene)

AlkyneAlkynyl

| {{chem2|RC\tCR′}}

| R-C#C-R'

| alkynyl-

-yne

| H-C#C-H
Acetylene
(Ethyne)

Benzene derivative

| Phenyl

| RC6H5
RPh

| File:Phenyl-group.svg

| phenyl-

-benzene

| 75px
Cumene
(Isopropylbenzene)

There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc. 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.

class="wikitable" style="background: #ffffff; text-align: center;width:550px"
Chemical class

! Group

! Formula

! Structural formula

! Prefix

! Suffix

! Example

haloalkanehalo

| RX

| R-X

| halo-

alkyl halide

| 65x65px
Chloroethane
(Ethyl chloride)

fluoroalkanefluoro

| RF

| R-F

| fluoro-

alkyl fluoride

| 92x92px
Fluoromethane
(Methyl fluoride)

chloroalkanechloro

| RCl

| R-Cl

| chloro-

alkyl chloride

| File:Chloromethane.svg
Chloromethane
(Methyl chloride)

bromoalkanebromo

| RBr

| R-Br

| bromo-

alkyl bromide

| 107x107px
Bromomethane
(Methyl bromide)

iodoalkaneiodo

| RI

| R-I

| iodo-

alkyl iodide

| File:Iodomethane.svg
Iodomethane
(Methyl iodide)

=Groups containing oxygen=

Compounds that contain C–O bonds each possess differing reactivity based upon the location and hybridization of the C–O bond, owing to the electron-withdrawing effect of sp-hybridized oxygen (carbonyl groups) and the donating effects of sp2-hybridized oxygen (alcohol groups).

class="wikitable" style="background: #ffffff; text-align: center;width:300px"
Chemical class

! Group

! Formula

! Structural formula

! Prefix

! Suffix

! Example

AlcoholHydroxyl

| ROH

| File:Hydroxy-group-bw.svg

| hydroxy-

-ol

| File:Methanol-2D.svg
Methanol

KetoneKetone

| RCOR′

| File:Ketone-group-2D-skeletal.svg

| -oyl- (-COR′)
or
oxo- (=O)

-one

| File:Butanone-skeletal-structure.svg
Butanone
(Methyl ethyl ketone)

AldehydeAldehyde

| RCHO

| File:Skeletal formula of an aldehyde group.svg

| formyl- (-COH)
or
oxo- (=O)

-al

| File:Acetaldehyde-skeletal.svg
Acetaldehyde
(Ethanal)

Acyl halideHaloformyl

| RCOX

| File:Acyl-halide-skeletal2D.svg

| carbonofluoridoyl-
carbonochloridoyl-
carbonobromidoyl-
carbonoiodidoyl-

-oyl fluoride
-oyl chloride
-oyl bromide
-oyl iodide

| File:Acetyl-chloride.svg
Acetyl chloride
(Ethanoyl chloride)

Carbonate

| Carbonate ester

| ROCOOR′

| File:Carbonate-group-skeletal.svg

| (alkoxycarbonyl)oxy-

| alkyl carbonate

| File:Triphosgen Strukturformel.svg
Triphosgene
(bis(trichloromethyl) carbonate)

Carboxylate

| Carboxylate

RCOO

| File:Carboxylate-resonance-hybrid.svg
File:Carboxylate-canonical-forms.svg

| carboxylato-

-oate

| File:Sodium-acetate-2D-skeletal.png
Sodium acetate
(Sodium ethanoate)

Carboxylic acid

| Carboxyl

RCOOH

| File:Carboxylic-acid-skeletal.svg

| carboxy-

-oic acid

| File:Acetic-acid-2D-skeletal.svg
Acetic acid
(Ethanoic acid)

EsterCarboalkoxy

| RCOOR′

| File:Ester-skeletal.svg

| alkanoyloxy-
or
alkoxycarbonyl

| alkyl alkanoate

| File:Ethyl butyrate.png
Ethyl butyrate
(Ethyl butanoate)

Hydroperoxide

| Hydroperoxy

| ROOH

| File:Hydroperoxide-group-2D.svg

| hydroperoxy-

| alkyl hydroperoxide

| File:TBHP.png
tert-Butyl hydroperoxide

Peroxide

| Peroxy

| ROOR′

| File:Peroxy-group.svg

| peroxy-

| alkyl peroxide

| File:Di-tert-butyl peroxide.svg
Di-tert-butyl peroxide

EtherEther

| ROR′

| File:Ether-(general).svg

| alkoxy-

| alkyl ether

| File:Diethyl ether chemical structure.svg
Diethyl ether
(Ethoxyethane)

HemiacetalHemiacetal

| R2CH(OR1)(OH)

| File:Hemiacetal general.svg

| alkoxy -ol

| -al alkyl hemiacetal

|

HemiketalHemiketal

| RC(ORʺ)(OH)R′

| File:Hemiketal-2D-skeletal.png

| alkoxy -ol

| -one alkyl hemiketal

|

AcetalAcetal

| RCH(OR′)(OR″)

| File:Acetal-2D-skeletal.png

| dialkoxy-

| -al dialkyl acetal

|

Ketal (or Acetal)Ketal (or Acetal)

| {{nowrap|RC(OR″)(OR‴)R′}}

| File:Ketal-2D-skeletal.png

| dialkoxy-

| -one dialkyl ketal

|

OrthoesterOrthoester

| {{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
1,2-Methylenedioxybenzene
(1,3-Benzodioxole)

Orthocarbonate esterOrthocarbonate ester

| {{nowrap|C(OR)(OR′)(OR″)(OR‴)}}

| File:Orthocarbonate-ester.svg

| tetralkoxy-

| tetraalkyl orthocarbonate

| File:Tetramethylorthocarbonat.svg
Tetramethoxymethane

Organic acid anhydrideCarboxylic anhydride

| {{nowrap|R1(CO)O(CO)R2}}

| File:FunktionelleGruppen Carbonsäureanhydrid.svg

|

| anhydride

| File:Butyric anhydride.svg
Butyric anhydride

=Groups containing nitrogen=

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

class="wikitable" style="background: #ffffff; text-align: center;width:700px"
Chemical class

! Group

! Formula

! Structural formula

! Prefix

! Suffix

! Example

AmideCarboxamide

| RCONR'R"

| File:Amide-(tertiary)-skeletal.svg

| carboxamido-
or
carbamoyl-

-amide

| File:Acetamide skeletal.svg
Acetamide
(Ethanamide)

Amidine

|Amidine

|R4C(NR1)(NR2R3)

|File:Amidines.svg

| amidino-

| -amidine

|File:Acetamidine-2D-skeletal.pngacetamidine

(acetimidamide)

Guanidine

|Guanidine

|RNC(NR2)2)

|File:Guanidine-group-2D-skeletal.svg

| Guanidin-

| -Guanidine

|File:Guanidinopropionic acid.pngGuanidinopropionic acid

rowspan="5" | Amines

| Primary amine

| RNH2

| File:1°-amino-group.png

| amino-

-amine

| File:Methylamine-2D.png
Methylamine
(Methanamine)

Secondary amine

| R'R"NH

| File:Amine-(secondary).png

| amino-

-amine

| File:Dimethylamine-2D.png
Dimethylamine

Tertiary amine

| R3N

| File:Amine-(tertiary).png

| amino-

-amine

| File:Trimethylamine chemical structure.png
Trimethylamine

4° ammonium ion

| R4N+

| File:Quaternary-ammonium-cation.svg

| ammonio-

-ammonium

| File:Choline-skeletal.svg
Choline

Hydrazone

|R'R"CN2H2

|File:Hydrazone-2D.png

|hydrazino-

| -hydrazine

|File:Benzophenone hydrazone-structure.png]]

rowspan="4" | Imine

| Primary ketimine

| RC(=NH)R'

| File:Imine-(primary)-skeletal.svg

| imino-

-imine

|

Secondary ketimine

| RC(=NR'')R'

| File:Imine-(secondary)-skeletal.svg

| imino-

-imine

|

Primary aldimine

| RC(=NH)H

| File:Aldimine-(primary)-skeletal.svg

| imino-

-imine

| File:Ethanimine skeletal.svg
Ethanimine

Secondary aldimine

| RC(=NR')H

| File:Aldimine-(secondary)-skeletal.svg

| imino-

-imine

|

ImideImide

| (RCO)2NR'

| File:Imide-group.svg

| imido-

| -imide

| File:Succinimide.svg
Succinimide
(Pyrrolidine-2,5-dione)

Azide

| Azide

| RN3

| File:Azide-2D.svg

| azido-

alkyl azide

| File:Phenyl azide-chemical.png
Phenyl azide
(Azidobenzene)

Azo compound

| Azo
(Diimide)

| RN2R'

| File:Azo-group.svg

| azo-

-diazene

| File:Methyl-orange-skeletal.png
Methyl orange
(p-dimethylamino-azobenzenesulfonic acid)

rowspan=2|Cyanates

| Cyanate

ROCN

| File:Cyanate-group.svg

| cyanato-

| alkyl cyanate

|File:Methyl cyanate.svg
Methyl cyanate

IsocyanateRNCO

| File:Isocyanate-group.svg

| isocyanato-

| alkyl isocyanate

| File:Methyl-isocyanate.svg
Methyl isocyanate

NitrateNitrate

| RONO2

| File:Nitrate-group-2D.svg

| nitrooxy-, nitroxy-

alkyl nitrate

| File:Amyl nitrate.svg
Amyl nitrate
(1-nitrooxypentane)

rowspan=2|Nitrile

| Nitrile

| RCN

| R-\!#N

| cyano-

| alkanenitrile
alkyl cyanide

| File:Benzonitrile structure.png
Benzonitrile
(Phenyl cyanide)

IsonitrileRNC

| File:Isonitrile structural formula.svg

| isocyano-

| alkaneisonitrile
alkyl isocyanide

| \ce{H3C}{-}\overset{+}{\ce{N}}\ce{#C^-}
Methyl isocyanide

NitriteNitrosooxy

| RONO

| File:Nitrite-group-2D.svg

| nitrosooxy-

alkyl nitrite

| File:Amyl nitrite.svg
Isoamyl nitrite
(3-methyl-1-nitrosooxybutane)

Nitro compound

| Nitro

| RNO2

| File:Nitro-group.svg

| nitro-

 

| File:Nitromethane2.png
Nitromethane

Nitroso compound

| Nitroso

RNO

| File:Nitroso-compound-2D.svg

| nitroso- (Nitrosyl-)

 

| File:Nitrosobenzene.png
Nitrosobenzene

Oxime

| Oxime

RCH=NOH

| File:General structure of oximes.svg

|  

Oxime

| File:acetoxime.svg
Acetone oxime
(2-Propanone oxime)

Pyridine derivative

| Pyridyl

| RC5H4N

|

File:4-pyridyl.svg

File:3-pyridyl.svg

File:2-pyridyl.svg

|

4-pyridyl
(pyridin-4-yl)

3-pyridyl
(pyridin-3-yl)

2-pyridyl
(pyridin-2-yl)

| -pyridine

| File:Nicotine skeletal.svg
Nicotine

Carbamate ester

| Carbamate

RO(C=O)NR2

| File:Carbamate-group-2D-skeletal.png

| (-carbamoyl)oxy-

-carbamate

| File:Isopropyl (3-chlorophenyl)carbamate 200.svg
Chlorpropham
(Isopropyl (3-chlorophenyl)carbamate)

=Groups containing sulfur=

Compounds that contain sulfur exhibit unique chemistry due to sulfur's ability to form more bonds than oxygen, its lighter analogue on the periodic table. Substitutive nomenclature (marked as prefix in table) is preferred over functional class nomenclature (marked as suffix in table) for sulfides, disulfides, sulfoxides and sulfones.

class="wikitable" style="background: #ffffff; text-align: center;width:800px"
Chemical class

! Group

! Formula

! Structural formula

! Prefix

! Suffix

! Example

Thiol

| Sulfhydryl

| RSH

| File:Thiol-group.svg

| sulfanyl-
(-SH)

| -thiol

| File:Ethanethiol-skeletal.svg
Ethanethiol

Sulfide
(Thioether)

| Sulfide

| RSR'

| File:Sulfide-group-2D.svg

| substituent sulfanyl-
(-SR')

| di(substituentsulfide

|
File:Dimethylsulfide.png

(Methylsulfanyl)methane (prefix) or
Dimethyl sulfide (suffix)

DisulfideDisulfide

| RSSR'

| File:Disulfide general formula.svg

| substituent disulfanyl-
(-SSR')

| di(substituentdisulfide

|
File:Dimethyl disulfide.PNG

(Methyldisulfanyl)methane (prefix) or
Dimethyl disulfide (suffix)

Sulfoxide

| Sulfinyl

| RSOR'

| File:Sulfoxide-2D.svg

| -sulfinyl-
(-SOR')

| di(substituentsulfoxide

| File:Dimethylsulfoxid.svg
(Methanesulfinyl)methane (prefix) or
Dimethyl sulfoxide (suffix)

Sulfone

| Sulfonyl

| RSO2R'

| File:Sulfone-2D.svg

| -sulfonyl-
(-SO2R')

| di(substituentsulfone

| File:DMSO2.svg
(Methanesulfonyl)methane (prefix) or
Dimethyl sulfone (suffix)

Sulfinic acidSulfino

| RSO2H

| 75px

| sulfino-
(-SO2H)

| -sulfinic acid

| File:Hypotaurine.svg
2-Aminoethanesulfinic acid

Sulfonic acidSulfo

| RSO3H

| File:Sulfonic-acid.svg

| sulfo-
(-SO3H)

| -sulfonic acid

| File:Benzenesulfonic-acid-2D-skeletal.png
Benzenesulfonic acid

Sulfonate esterSulfo

| RSO3R'

| File:Sulfonic-ester.svg

| (-sulfonyl)oxy-
or
alkoxysulfonyl-

| R R-sulfonate'

| File:StructureMeOTf.svg
Methyl trifluoromethanesulfonate or
Methoxysulfonyl trifluoromethane (prefix)

rowspan=2|Thiocyanate

| Thiocyanate

RSCN

| File:Thiocyanate-group.svg

| thiocyanato-
(-SCN)

| substituent thiocyanate

| File:Phenyl thiocyanate.svg
Phenyl thiocyanate

IsothiocyanateRNCS

| File:Isothiocyanate-group.svg

| isothiocyanato-
(-NCS)

| substituent isothiocyanate

| File:Allyl-isothiocyanate-2D-skeletal.png
Allyl isothiocyanate

Thioketone

| Carbonothioyl

| RCSR'

| File:Thioketone-skeletal.svg

| -thioyl-
(-CSR')
or
sulfanylidene-
(=S)

| -thione

| File:Thiobenzophenone-2D-skeletal.png
Diphenylmethanethione
(Thiobenzophenone)

Thial

| Carbonothioyl

| RCSH

| File:Thial-skeletal.svg

| methanethioyl-
(-CSH)
or
sulfanylidene-
(=S)

| -thial

|

rowspan=2| Thiocarboxylic acid

| Carbothioic S-acid

| RC=OSH

| File:Thioic acid.svg

| mercaptocarbonyl-

| -thioic S-acid

| File:Thiobenzoic acid.svg
Thiobenzoic acid
(benzothioic S-acid)

Carbothioic O-acid

| RC=SOH

| File:Thioic O-acid.svg

| 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
S-methyl thioacrylate
(S-methyl prop-2-enethioate)

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
Dithiobenzoic acid
(Benzenecarbodithioic acid)

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.

class="wikitable" style="background: #ffffff; text-align: center;width:800px"
Chemical class

! Group

! Formula

! Structural formula

! Prefix

! Suffix

! Example

Phosphine
(Phosphane)
Phosphino

| R3P

| File:Phosphine-general.svg

| phosphanyl-

-phosphane

| File:Methylpropylphosphane-skeletal.svg
Methylpropylphosphane

Phosphonic acid

| Phosphono

| RP(=O)(OH)2

| File:Phosphonic-acid.svg

| phosphono-

| substituent phosphonic acid

| File:Benzylphosphonic-acid-2D-skeletal.png
Benzylphosphonic acid

rowspan=2| Phosphate

| rowspan=2| Phosphate

| rowspan=2| ROP(=O)(OH)2

| rowspan=2| File:Phosphate-group.svg

| rowspan=2| phosphonooxy-
or
O-phosphono- (phospho-)

| rowspan=2| substituent phosphate

| File:G3P-2D-skeletal.png
Glyceraldehyde 3-phosphate (suffix)

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-
or
O-[(alkoxy)hydroxyphosphoryl]-

| rowspan=2|di(substituent) hydrogen phosphate
or
phosphoric 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 classGroupFormulaStructural formulaPrefixSuffixExample
Boronic acidBoronoRB(OH)2File:Boronic-acid-2D.svgBorono-substituent
boronic acid
{{center|File:Phenylboronic acid.png
Phenylboronic acid}}
Boronic esterBoronateRB(OR)2File:Boronate-ester-2D.svgO-[bis(alkoxy)alkylboronyl]-substituent
boronic acid
di(substituent) ester
Borinic acidBorinoR2BOHFile:Borinic-acid-2D.svgHydroxyborino-di(substituent)
borinic acid
Borinic esterBorinateR2BORFile:Borinate-ester-2D.svgO-[alkoxydialkylboronyl]-di(substituent)
borinic acid
substituent ester
{{center|File:2-APB.png
Diphenylborinic acid 2-aminoethyl ester
(2-Aminoethoxydiphenyl borate)}}

= Groups containing metals =

class="wikitable"

|+

!Chemical class

!Structural formula

!Prefix

!Suffix

!Example

Alkyllithium

|RLi

| rowspan="4" |(tri/di)alkyl-

| -lithium

|71x71px

methyllithium

Alkylmagnesium halide

|RMgX (X=Cl, Br, I){{Ref label|halogen|note 1|note 1}}

| -magnesium halide

|97x97px

methylmagnesium chloride

Alkylaluminium

|Al2R6

| -aluminium

|109x109px

trimethylaluminium

Silyl ether

|R3SiOR

| -silyl ether

|File:Trimethylsilyl triflate.svg

trimethylsilyl triflate

{{Note label|halogen|note 1|note 1}} Fluorine is too electronegative to be bonded to magnesium; it becomes an ionic salt instead.

=Names of radicals or moieties=

These names are used to refer to the moieties themselves or to radical species, and also to form the names of halides and substituents in larger molecules.

When the parent hydrocarbon is unsaturated, the suffix ("-yl", "-ylidene", or "-ylidyne") replaces "-ane" (e.g. "ethane" becomes "ethyl"); otherwise, the suffix replaces only the final "-e" (e.g. "ethyne" becomes "ethynyl").

When used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a methylene bridge (methanediyl) has two single bonds, whereas a 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.

class="wikitable"
Chemical classGroupFormulaStructural formulaPrefixSuffixExample
Single bondR•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 bondR:?-ylidene{{center|Methylidene}}
Triple bondR⫶?-ylidyne{{center|Methylidyne}}
Carboxylic acyl radicalAcylR−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}}

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