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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.
Benzyl acetate has an ester functional group (in red), an acetyl moiety (circled with green) and a benzyloxy moiety (circled with orange). Other divisions can be made.
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 4.6 Groups 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.
Crystallography
The 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 SO42-). 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.
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 Group class Alkane Formula Structural Formula Prefix Suffix Example
Alkyl R(CH2)n H
alkyl-
-ane Ethane
Alkene
Alkenyl R2C=CR2
alkenyl-
Alkyne
Alkynyl RCCR'
alkynyl-
-yne
Acetylene (Ethyne)
RC6H5 RPh
phenyl-
benzyl-
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.
Chemical class
Group Formula
Structural Formula
Prefix
Suffix
Example
haloalkane
halo
RX
halo-
alkyl halide
fluoroalkane
fluoro
RF
fluoro-
alkyl fluoride
chloroalkane chloro
RCl
chloro-
alkyl chloride
bromoalkane bromo
RBr
bromo-
alkyl bromide
iodoalkane
iodo
RI
iodo-
alkyl iodide
Alcohol
Hydroxyl
ROH
hydroxy-
-ol Methanol
Ketone
Carbonyl
RCOR'
-one
Aldehyde
Aldehyde
RCHO
Acyl halide
Haloformyl
RCOX
carbonofluoridoylcarbonochloridoylcarbonobromidoylcarbonoiodidoyl-
Carbonate
Carbonate
ester
ROCOOR
Carboxylate
Carboxylate
RCOO
carboxy-
-oate
Carboxylic acid
Carboxyl
RCOOH
carboxy-
Ester
Ester
RCOOR'
alkyl alkanoate
Methoxy
Methoxy
ROCH3
Hydroperoxide
Hydroperoxy
ROOH
hydroperoxy-
alkyl hydroperoxide
Peroxide
Peroxy
ROOR
peroxy-
Ether
Ether
ROR'
alkoxy-
alkyl ether
Hemiacetal
Hemiacetal
RCH(OR')(OH)
alkoxy -ol
-al alkyl hemiacetal -one alkyl hemiketal -al dialkyl acetal -one dialkyl ketal
Hemiketal
Hemiketal
RC(OR)(OH)R'
alkoxy -ol
Acetal
Acetal
RCH(OR')(OR")
dialkoxy-
RC(OR)(OR)R'
dialkoxy-
RC(OR')(OR)(OR)
trialkoxytetralkoxytetraalkyl orthocarbonate
Amide
Carboxamide RCONR2
Primary amine
RNH2
amino-
R2NH
amino-
-amine
Dimethylamine
R3N
amino-
-amine Trimethylamine
4 ammonium ion
R4N+
ammonio-
-ammonium Choline
Primary ketimine
RC(=NH)R'
imino-
-imine
RC(=NR)R'
imino-
-imine
RC(=NH)H
imino-
-imine Ethanimine
imino-
-imine
Imide
Imide
(RCO)2NR'
imido-
Azide
Azide
RN3
azido-
Azo compound
Azo (Diimide)
RN2R'
azo-
-diazene
ROCN
cyanato-
RNCO
isocyanato-
alkyl isocyanate
Methyl isocyanate
Nitrate
Nitrate
RONO2
nitrooxy-, nitroxy-
Nitrile
Nitrile
RCN
cyano-
alkyl cyanide
Methyl isocyanide
Nitrite
Nitrosooxy
RONO
nitrosooxy-
alkyl nitrite
Nitro compound
Nitro
RNO2
nitroNitromethane
Nitroso compound
Nitroso
RNO
Nitrosobenzene
Pyridine derivative
Pyridyl
RC5H4N
-pyridine Nicotine
Group
Formula
Structural Formula
Prefix sulfanyl(-SH)
Suffix
Example
Sulfhydryl
RSH
- thiol
Ethanethiol
Sulfide (Thioether)
Sulfide
RSR'
substituent sulfanyl(-SR')
Disulfide
Disulfide
RSSR'
substituent disulfanyl(-SSR')
Sulfoxide
Sulfinyl
RSOR'
-sulfinyl(-SOR')
Sulfone
Sulfonyl
RSO2R'
-sulfonyl(-SO2R')
Sulfinic acid
Sulfino
RSO2H
sulfino(-SO2H)
2-Aminoethanesulfinic acid
Sulfonic acid
Sulfo
RSO3H
sulfo(-SO3H)
- sulfonic acid
Benzenesulfonic acid
Thiocyanate Thiocyanate
RSCN
Isothiocyanate RNCS
Thione
Carbonothioyl RCSR'
- thione
Diphenylmethanethione (Thiobenzophenone)
Thial
Carbonothioyl RCSH
- thial
Group Phosphino
Structural Formula
Prefix phosphanyl-
Suffix -phosphane
Example
Phosphono
Benzylphosphonic acid
Phosphate
Phosphate
ROP(=O) (OH)2
substituent phosphate
di(substituent ) DNA hydrogen phosphate or or O[(2Guanidinoethoxy)hydroxyphosphoryl]Lserine (prefix) O-[(alkoxy)hydroxyphosphoryl]phosphoric acid (Lombricine) di(substituent ) ester
Boronic acid
Borono
RB(OH)2
Borono-
Boronate RB(OR)2
Borino
R2BOH
Hydroxyborino-
Borinate R2BOR
O[alkoxydialkylboronyl]-
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
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