官能基

関: function、functional

WordNet

perform as expected when applied; "The washing machine wont go unless its plugged in"; "Does this old car still run well?"; "This old radio doesnt work anymore" (同)work, operate, go, run
(mathematics) a mathematical relation such that each element of a given set (the domain of the function) is associated with an element of another set (the range of the function) (同)mathematical function, single-valued function, map, mapping
a relation such that one thing is dependent on another; "height is a function of age"; "price is a function of supply and demand"
the actions and activities assigned to or required or expected of a person or group; "the function of a teacher"; "the government must do its part"; "play its role" (同)office, part, role
what something is used for; "the function of an auger is to bore holes"; "ballet is beautiful but what use is it?" (同)purpose, role, use
a formal or official social gathering or ceremony; "it was a black-tie function"
arrange into a group or groups; "Can you group these shapes together?"
(chemistry) two or more atoms bound together as a single unit and forming part of a molecule (同)radical, chemical group
any number of entities (members) considered as a unit (同)grouping
a set that is closed, associative, has an identity element and every element has an inverse (同)mathematical group
form a group or group together (同)aggroup
relating to or based on function especially as opposed to structure; "the problem now is not a constitutional one; it is a functional one"; "delegates elected on a functional rather than a geographical basis"
fit or ready for use or service; "the toaster was still functional even after being dropped"; "the lawnmower is a bit rusty but still usable"; "an operational aircraft"; "the dishwasher is now in working order" (同)usable, useable, operable, operational
designed for or adapted to a function or use; "functional education selects knowledge that is concrete and usable rather than abstract and theoretical"; "functional architecture"
designed for or capable of a particular function or use; "a style of writing in which every word is functional"; "functional architecture"
involving or affecting function rather than physiology; "functional deafness"
the activity of putting things together in groups
a system for classifying things into groups (同)pigeonholing
arranged into groups (同)sorted

PrepTutorEJDIC

(人・物の果たすべき)『働き』,機能,役目;《しばしば複数形で》職務 / (公式の)儀式,《話》大きな催し(集まり),式典 / (数学で)関数 / 〈機械などが〉『機能を果たす』,動く / (…の)役目をする,代用となる《+『as』+『名』》
(…の)『群れ』,集まり,小集団《+of+名》 / (主義・系統・種類などを同じくする人・物の)『派』,『団体』 / (ポミュラーソング歌手の)グループ / (動・植物分類上の)群;(化学の)基,原子団;(地質学上の)界;(数学の)群;(言語学上の)語派 / …‘を'一群に集める,一団にする《+『名』+『together』》 / (系統的に)…‘を'分類する,調和よく配合する《+『名』+『together』》 / 集まる,群(集団)をなす
『機能上の』 / (余分なものが無く)機能的な,実用的な / (数学で)関数の
グループに分けること;分類法 / (集まった物の)配置,配合

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/22 14:11:56」(JST)

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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.

In organic chemistry, functional groups are 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 /ˈmɔɪəti/ 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. This definition allows for a recursive nature, where moieties may contain functional groups which may contain moieties, etc. almost without limit (by definition, a functional group or moiety must have more than one atom, and the combination and structure must be of interest in itself). For example, methyl para-hydroxybenzoate contains a phenol functional group within the acyl moiety, which in turn is part of the paraben 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.

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

An aldol reaction of acetone with another ketone is not possible, because it would self-condense instead. The problem can be circumvented by replacing the ketone with the corresponding silyl enol ether in a Mukaiyama aldol addition. The silicon is then removed.

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, Na
2SO
4 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.

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 double bonds. Each one differs in type (and scope) of reactivity.

Chemical class	Group	Formula	Prefix	Suffix	Example
Alkane	Alkyl	R(CH₂)_nH	alkyl-	-ane	Ethane
Alkene	Alkenyl	R₂C=CR₂	alkenyl-	-ene	Ethylene (Ethene)
Alkyne	Alkynyl	RC≡CR'	alkynyl-	-yne	Acetylene (Ethyne)
Benzene derivative	Phenyl	RC₆H₅ RPh	phenyl-	-benzene	Cumene (2-phenylpropane)
Toluene derivative	Benzyl	RCH₂C₆H₅ RBn	benzyl-	1-(substituent)toluene	Benzyl bromide (α-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.

Chemical class	Group	Formula	Prefix	Suffix	Example
haloalkane	halo	RX	halo-	alkyl halide	Chloroethane (Ethyl chloride)
fluoroalkane	fluoro	RF	fluoro-	alkyl fluoride	Fluoromethane (Methyl fluoride)
chloroalkane	chloro	RCl	chloro-	alkyl chloride	Chloromethane (Methyl chloride)
bromoalkane	bromo	RBr	bromo-	alkyl bromide	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 class	Group	Formula	Prefix	Suffix	Example
Alcohol	Hydroxyl	ROH	hydroxy-	-ol	Methanol
Ketone	Carbonyl	RCOR'	-oyl- (-COR') or oxo- (=O)	-one	Butanone (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	Carbonate ester	ROCOOR	(alkoxycarbonyl)oxy-	alkyl carbonate	Triphosgene (bis(trichloromethyl) carbonate)
Carboxylate	Carboxylate	RCOO⁻	carboxy-	-oate	Sodium 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 hydroperoxide	tert-Butyl hydroperoxide
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(ORʺ)(OH)R'	alkoxy -ol	-one alkyl hemiketal
Acetal	Acetal	RCH(OR')(OR")	dialkoxy-	-al dialkyl acetal
Ketal (or Acetal)	Ketal (or Acetal)	RC(ORʺ)(OR‴)R'	dialkoxy-	-one dialkyl ketal
Orthoester	Orthoester	RC(OR')(ORʺ)(OR‴)	trialkoxy-
Heterocycle	Methylenedioxy	PhOCOPh	methylenedioxy-	-dioxole	1,2-Methylenedioxybenzene (1,3-Benzodioxole)
Orthocarbonate ester	Orthocarbonate ester	C(OR)(OR')(ORʺ)(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 class	Group	Formula	Prefix	Suffix	Example
Amide	Carboxamide	RCONR₂	carboxamido- or carbamoyl-	-amide	Acetamide (Ethanamide)
Amines	Primary amine	RNH₂	amino-	-amine	Methylamine (Methanamine)
	Secondary amine	R₂NH	amino-	-amine	Dimethylamine
	Tertiary amine	R₃N	amino-	-amine	Trimethylamine
	4° ammonium ion	R₄N⁺	ammonio-	-ammonium	Choline
Imine	Primary ketimine	RC(=NH)R'	imino-	-imine
	Secondary ketimine	RC(=NR)R'	imino-	-imine
	Primary aldimine	RC(=NH)H	imino-	-imine	Ethanimine
	Secondary aldimine	RC(=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
Cyanates	Isocyanate	RNCO	isocyanato-	alkyl isocyanate	Methyl isocyanate
Nitrate	Nitrate	RONO₂	nitrooxy-, nitroxy-	alkyl nitrate	Amyl nitrate (1-nitrooxypentane)
Nitrile	Nitrile	RCN	cyano-	alkanenitrile alkyl cyanide	Benzonitrile (Phenyl cyanide)
Nitrile	Isonitrile	RNC	isocyano-	alkaneisonitrile alkyl isocyanide	Methyl isocyanide
Nitrite	Nitrosooxy	RONO	nitrosooxy-	alkyl nitrite	Isoamyl nitrite (3-methyl-1-nitrosooxybutane)
Nitro compound	Nitro	RNO₂	nitro-		Nitromethane
Nitroso compound	Nitroso	RNO	nitroso- (Nitrosyl-)		Nitrosobenzene
Pyridine derivative	Pyridyl	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.

Chemical class	Group	Formula	Prefix	Suffix	Example
Thiol	Sulfhydryl	RSH	sulfanyl- (-SH)	-thiol	Ethanethiol
Sulfide (Thioether)	Sulfide	RSR'	substituent sulfanyl- (-SR')	di(substituent) sulfide	(Methylsulfanyl)methane (prefix) or Dimethyl sulfide (suffix)
Disulfide	Disulfide	RSSR'	substituent disulfanyl- (-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	RSO₂H	sulfino- (-SO₂H)	-sulfinic acid	2-Aminoethanesulfinic acid
Sulfonic acid	Sulfo	RSO₃H	sulfo- (-SO₃H)	-sulfonic acid	Benzenesulfonic acid
Thiocyanate	Thiocyanate	RSCN	thiocyanato- (-SCN)	substituent thiocyanate	Phenyl thiocyanate
Thiocyanate	Isothiocyanate	RNCS	isothiocyanato- (-NCS)	substituent isothiocyanate	Allyl isothiocyanate
Thione	Carbonothioyl	RCSR'	-thioyl- (-CSR') or sulfanylidene- (=S)	-thione	Diphenylmethanethione (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.

Chemical class	Group	Formula	Prefix	Suffix	Example
Phosphine (Phosphane)	Phosphino	R₃P	phosphanyl-	-phosphane	Methylpropylphosphane
Phosphonic acid	Phosphono	RP(=O)(OH)₂	phosphono-	substituent phosphonic acid	Benzylphosphonic acid
Phosphate	Phosphate	ROP(=O)(OH)₂	phosphonooxy- or O-phosphono- (phospho-)	substituent phosphate	Glyceraldehyde 3-phosphate (suffix)
Phosphate	Phosphate	ROP(=O)(OH)₂	phosphonooxy- or O-phosphono- (phospho-)	substituent phosphate	O-Phosphonocholine (prefix) (Phosphocholine)
Phosphodiester	Phosphate	HOPO(OR)₂	[(alkoxy)hydroxyphosphoryl]oxy- or O-[(alkoxy)hydroxyphosphoryl]-	di(substituent) hydrogen phosphate or phosphoric acid di(substituent) ester	DNA
Phosphodiester	Phosphate	HOPO(OR)₂			O‑[(2‑Guanidinoethoxy)hydroxyphosphoryl]‑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.

Chemical class	Group	Formula	Prefix	Suffix	Example
Boronic acid	Borono	RB(OH)₂	Borono-	substituent boronic acid	Phenylboronic acid
Boronic ester	Boronate	RB(OR)₂	O-[bis(alkoxy)alkylboronyl]-	substituent boronic acid di(substituent) ester
Borinic acid	Borino	R₂BOH	Hydroxyborino-	di(substituent) borinic acid
Borinic ester	Borinate	R₂BOR	O-[alkoxydialkylboronyl]-	di(substituent) borinic acid substituent ester	Diphenylborinic acid 2-aminoethyl ester (2-Aminoethoxydiphenyl borate)

References

^ Compendium of Chemical Terminology (IUPAC "Gold Book") http://goldbook.iupac.org/F02555.html
^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7
^ 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://goldbook.iupac.org/M03968.html

External links

IUPAC Blue Book (organic nomenclature)
IUPAC ligand abbreviations (pdf)
_chemical_formula_moiety in CIF dictionary
Functional group synthesis from organic-reaction.com

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Evaluation of protease resistance and toxicity of amyloid-like food fibrils from whey, soy, kidney bean, and egg white.

Lassé M1, Ulluwishewa D2, Healy J3, Thompson D4, Miller A5, Roy N2, Chitcholtan K6, Gerrard JA7.
Food chemistry.Food Chem.2016 Feb 1;192:491-8. doi: 10.1016/j.foodchem.2015.07.044. Epub 2015 Jul 11.
The structural properties of amyloid fibrils combined with their highly functional surface chemistry make them an attractive new food ingredient, for example as highly effective gelling agents. However, the toxic role of amyloid fibrils in disease may cause some concern about their food safety becau
PMID 26304377

Molecularly imprinted calixarene fiber for solid-phase microextraction of four organophosphorous pesticides in fruits.

Li JW1, Wang YL1, Yan S1, Li XJ2, Pan SY1.
Food chemistry.Food Chem.2016 Feb 1;192:260-7. doi: 10.1016/j.foodchem.2015.07.018. Epub 2015 Jul 7.
Calixarene was used as a functional monomer to fabricate a molecularly imprinted polymer (MIP) by sol-gel technique for solid-phase microextraction (SPME) of parathion-methyl and its structural analogs. The MIP-coated fiber possessed excellent thermal and chemical stability as well as high extractio
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Effect of pulsed electric fields assisted acetylation on morphological, structural and functional characteristics of potato starch.

Hong J1, Chen R1, Zeng XA2, Han Z3.
Food chemistry.Food Chem.2016 Feb 1;192:15-24. doi: 10.1016/j.foodchem.2015.06.058. Epub 2015 Jun 20.
Pulsed electric fields (PEF)-assisted acetylation of potato starch with different degree of substitution (DS) was prepared and effects of PEF strength, reaction time, starch concentration on DS were studied by response surface methodology. Results showed DS was increased from 0.054 (reaction time of
PMID 26304315

Japanese Journal

Effect of olprinone on liver microstructure in rat partial liver transplantation.

Yamanaka Kenya,Hatano Etsuro,Iguchi Khota,Yamamoto Gen,Sato Motohiko,Toriguchi Kan,Tanabe Kazutaka,Takemoto Kenji,Nakamura Kojiro,Koyama Noriyuki,Narita Masato,Nagata Hiromitsu,Taura Kojiro,Uemoto Shinji
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… However, partial grafts do not meet the functional demands of recipients and lead to small-for-size syndrome (SFSS). … In the OLP group, we inserted an osmotic pump with OLP into the peritoneal cavity 48 h before liver graft sampling. … [Results]In the OLP group 1 h after PLT, the sinusoidal endothelial cells of the liver were well preserved and we observed few vacuolar structures in hepatocytes. …
NAID 120005298136

Effect of Body Weight-supported Walking on Exercise Capacity and Walking Speed in Patients with Knee Osteoarthritis: A Randomized Controlled Trial

Watanabe Shinichi,Someya Fujiko
Journal of the Japanese Physical Therapy Association 16, 004, 2013-06-28
… mean age, 76.0±7.5 y) were randomly assigned to BWSTT or FBWTT group. … Main measures were 10-meter walking test (10MWT), functional reach test (FRT), timed get up and go test (TUG), one-leg standing test, 6-minute walking test (6MWT), the parameters set on the treadmill, MOS Short-Form 36-Item Health Survey (SF36), Japanese Knee Osteoarthritis Measure (JKOM). … There were no significant improvements in either group assessed by the FRT, one-leg standing time test, TUG, or SF -36 questionnaire. …
NAID 120005302303

A GENERALIZATION OF PERSPECTIVE FUNCTION (Research on structures of operators via methods in geometry and probability theory)

KIAN MOHSEN
数理解析研究所講究録 1839, 95-109, 2013-06-00
NAID 110009595769

「function」

　　[★]

n.

機能、(数学)関数、(化学)官能基

survival as a function of HbA1c in people with type 2 diabetes HbA1cの機能を考慮（指標に）した2型糖尿病の患者の生存（予後）

Figure 2A shows survival as a function of device removal during index hpspitalization, censored at 1 year or date of last contact. (Figure2Aはは最初の入院中における心臓デバイス除去に関する生存曲線で退院後1年もしくは最後の接触で打ち切っている)