Difference between revisions of "Functional class nomenclature"

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'''Functional class nomenclature''', also called '''radicofunctional nomenclature''', is a type of [[chemical nomenclature]] used for [[organic compound]]s.<ref>{{BlueBook1993|pages=14–15}}.</ref> It is similar in principle to the [[compositional nomenclature]] used for [[inorganic compound]]s.<ref>{{RedBook2005|pages=68–82}}.</ref> Examples of functional class names include "[[methyl alcohol]]" and "[[acetyl chloride]]".<ref name="BlueBook04">{{BlueBook2004|pages=47–50}}.</ref>
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'''Functional class nomenclature''', also called '''radicofunctional nomenclature''', is a type of [[chemical nomenclature]] used for [[organic compound]]s.<ref>{{BlueBook1993|pages=14–15}}.</ref> It is similar in principle to the [[compositional nomenclature]] used for [[inorganic compound]]s.<ref>{{RedBook2005|pages=68–82}}.</ref> Examples of functional class names include "[[methyl alcohol]]" and "[[acetic anhydride]]".<ref name="BlueBook04">{{BlueBook2004|pages=47–50}}.</ref>
  
 
Functional class nomenclature was once widely used for organic compounds, but it has steadily been superceded by [[substitutive nomenclature]].<ref name="BlueBook04"/> It remains the usual method of naming [[N-oxide|''N''-oxides]] and other ''N''-chalcogenides, [[acid anhydride]]s, [[ester]]s, and [[acyl halide]]s and pseudohalides, and is often used for other [[functional class]]es such as [[azine]]s, [[oxime]]s, [[hydrazone]]s, [[semicarbazone]]s, [[carbohydrazone]]s, [[acetal]]s, and [[hemiacetal]]s.<ref name="BlueBook04"/>
 
Functional class nomenclature was once widely used for organic compounds, but it has steadily been superceded by [[substitutive nomenclature]].<ref name="BlueBook04"/> It remains the usual method of naming [[N-oxide|''N''-oxides]] and other ''N''-chalcogenides, [[acid anhydride]]s, [[ester]]s, and [[acyl halide]]s and pseudohalides, and is often used for other [[functional class]]es such as [[azine]]s, [[oxime]]s, [[hydrazone]]s, [[semicarbazone]]s, [[carbohydrazone]]s, [[acetal]]s, and [[hemiacetal]]s.<ref name="BlueBook04"/>
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{| class="wikitable"
 +
|-
 +
! Rule
 +
! Class name
 +
! Notes
 +
|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_730.htm C-103.1]<br/>R-5.3.1
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| fluoride<br/>chloride<br/>bromide<br/>iodide
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|
 +
|-
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| R-5.3.3.2
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| oxide
 +
| for azoxy compounds
 +
|-
 +
| R-5.3.4
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| azide
 +
|
 +
|-
 +
| R-5.4.3
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| imine
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| functional modifier, added after name of carbonyl compound
 +
|-
 +
| R-5.4.5
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| oxide
 +
| for amine oxides
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_202.htm C-201.3]<br/>R-5.5.1.1
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| alcohol
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| not used for phenols
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_390.htm C-511.5]
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| hydrosulfide
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| "mercaptan" is not recommended, but widely used
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_227.htm C-211.3]<br/>R-5.5.4.2
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| ether<br/>sulfide<br/>selenide<br/>telluride
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|
 +
|-
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| R-5.5.4.4
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| oxide
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| functional modifier for oxiranes, added after name of alkene
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_245.htm C-218]<br/>R-5.5.5
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| hydroperoxide<br/>peroxide
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|
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|-
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| R-5.5.6
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| hydropolysulfide<br/>polysulfide
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| and chalcogen analogues; "poly" is replaced by "di", "tri" etc.
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|-
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| R-5.5.7
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| sulfoxide<br/>sulfone<br/>selenoxide<br/>selenone
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|
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_267.htm C-312.2]<br/>R-5.6.2.1
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| ketone
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|
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_298.htm C-331.1]<br/>R-5.6.4.1
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| acetal<br/>ketal
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| and chalcogen analogues
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|-
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| R-5.6.4.2
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| hemiacetal
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| and chalcogen analogues
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/93/r93_469.htm R-5.6.6.1]
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| oxime
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| functional modifier, added after name of carbonyl compound
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_620.htm C-922.1]<br/>[http://www.acdlabs.com/iupac/nomenclature/93/r93_469.htm R-5.6.6.2]
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| hydrazone
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| functional modifier, added after name of carbonyl compound
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_623.htm C-923.1]<br/>[http://www.acdlabs.com/iupac/nomenclature/93/r93_469.htm R-5.6.6.3]
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| [[azine]]
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| functional modifier, added after name of carbonyl compound
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_676.htm C-982.1]<br/>[http://www.acdlabs.com/iupac/nomenclature/93/r93_469.htm R-5.6.6.4]
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| semicarbazone<br/>thiosemicarbazone<br/>selenosemicarbazone
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| functional modifier, added after name of carbonyl compound
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_363.htm C-463]<br/>R-5.7.4.2
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| ''see text''
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| for esters use name of anion
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_380.htm C-481.1]<br/>R-5.7.6
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| fluoride<br/>chloride<br/>bromide<br/>iodide
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| functional modifiers for acyl halides, added after name of acyl group
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|-
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| [http://www.acdlabs.com/iupac/nomenclature/79/r79_383.htm C-491]<br/>R-5.7.7.1
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| anhydride
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| functional modifier, replaces "acid" for symmetrical acid anhydrides
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|-
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| R-5.7.7.3
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| thioanhydride
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| functional modifier, replaces "acid" for symmetrical acid thioanhydrides
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|-
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| R-5.7.9.1
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| cyanide
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|
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|-
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| R-5.7.9.2
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| isocyanide<br/>cyanate<br/>isocyanate<br/>fulminate<br/>thiocyanate<br/>isothiocyanate<br/>selenocyanate<br/>isoselenocyanate
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| "isonitrile" and "carbylamine" have been used for isocyanide, but are not recommended
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|-
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| R-5.7.9.3
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| oxide
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| functional modifier for nitrile oxides, added after name of nitrile
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|-
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| R-5.8.2
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| cation
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|
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|-
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| R-5.8.3
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| anion
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|
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|-
 +
|}
  
 
==References==
 
==References==

Latest revision as of 10:23, 2 July 2010

Functional class nomenclature, also called radicofunctional nomenclature, is a type of chemical nomenclature used for organic compounds.[1] It is similar in principle to the compositional nomenclature used for inorganic compounds.[2] Examples of functional class names include "methyl alcohol" and "acetic anhydride".[3]

Functional class nomenclature was once widely used for organic compounds, but it has steadily been superceded by substitutive nomenclature.[3] It remains the usual method of naming N-oxides and other N-chalcogenides, acid anhydrides, esters, and acyl halides and pseudohalides, and is often used for other functional classes such as azines, oximes, hydrazones, semicarbazones, carbohydrazones, acetals, and hemiacetals.[3]

Rule Class name Notes
C-103.1
R-5.3.1 		fluoride
chloride
bromide
iodide
R-5.3.3.2 oxide for azoxy compounds
R-5.3.4 azide
R-5.4.3 imine functional modifier, added after name of carbonyl compound
R-5.4.5 oxide for amine oxides
C-201.3
R-5.5.1.1 		alcohol not used for phenols
C-511.5 hydrosulfide "mercaptan" is not recommended, but widely used
C-211.3
R-5.5.4.2 		ether
sulfide
selenide
telluride
R-5.5.4.4 oxide functional modifier for oxiranes, added after name of alkene
C-218
R-5.5.5 		hydroperoxide
peroxide
R-5.5.6 hydropolysulfide
polysulfide 		and chalcogen analogues; "poly" is replaced by "di", "tri" etc.
R-5.5.7 sulfoxide
sulfone
selenoxide
selenone
C-312.2
R-5.6.2.1 		ketone
C-331.1
R-5.6.4.1 		acetal
ketal 		and chalcogen analogues
R-5.6.4.2 hemiacetal and chalcogen analogues
R-5.6.6.1 oxime functional modifier, added after name of carbonyl compound
C-922.1
R-5.6.6.2 		hydrazone functional modifier, added after name of carbonyl compound
C-923.1
R-5.6.6.3 		azine functional modifier, added after name of carbonyl compound
C-982.1
R-5.6.6.4 		semicarbazone
thiosemicarbazone
selenosemicarbazone 		functional modifier, added after name of carbonyl compound
C-463
R-5.7.4.2 		see text for esters use name of anion
C-481.1
R-5.7.6 		fluoride
chloride
bromide
iodide 		functional modifiers for acyl halides, added after name of acyl group
C-491
R-5.7.7.1 		anhydride functional modifier, replaces "acid" for symmetrical acid anhydrides
R-5.7.7.3 thioanhydride functional modifier, replaces "acid" for symmetrical acid thioanhydrides
R-5.7.9.1 cyanide
R-5.7.9.2 isocyanide
cyanate
isocyanate
fulminate
thiocyanate
isothiocyanate
selenocyanate
isoselenocyanate 		"isonitrile" and "carbylamine" have been used for isocyanide, but are not recommended
R-5.7.9.3 oxide functional modifier for nitrile oxides, added after name of nitrile
R-5.8.2 cation
R-5.8.3 anion

References

  1. ↑ A Guide to IUPAC Nomenclature of Organic Compounds; IUPAC Recommendations 1993; Blackwell Science: Oxford, 1993; pp 14–15. ISBN 0-632-03488-2, <http://www.acdlabs.com/iupac/nomenclature/>.
  2. ↑ Nomenclature of Inorganic Chemistry; IUPAC Recommendations 2005; Royal Society of Chemistry: Cambridge, 2005; pp 68–82. ISBN 0-85404-438-8, <http://www.iupac.org/publications/books/rbook/Red_Book_2005.pdf>.
  3. ↑ 3.0 3.1 3.2 Nomenclature of Organic Chemistry; IUPAC Provisional Recommendations 2004; IUPAC, 2004; pp 47–50, <http://old.iupac.org/reports/provisional/abstract04/favre_310305.html>.
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