Difference between revisions of "Functional class nomenclature"

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Functional class nomenclature was once widely used for organic compounds, but it has steadily been superceded by [[substitutive nomenclature]].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Functional class nomenclature was once widely used for organic compounds, but it has steadily been superceded by [[substitutive nomenclature]].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
 +
|-
 +
| R-5.3.1
 +
| fluoride<br/>chloride<br/>bromide<br/>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
 +
|-
 +
| R-5.5.1.1
 +
| alcohol
 +
|
 +
|-
 +
| R-5.5.1.2
 +
| mercaptan<br/>selenol<br/>tellurol
 +
| no longer recommended
 +
|-
 +
| R-5.5.4.2
 +
| ether<br/>sulfide<br/>selenide<br/>telluride
 +
|
 +
|-
 +
| R-5.5.4.4
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| oxide
 +
| functional modifier for oxiranes, added after name of alkene
 +
|-
 +
| R-5.5.5
 +
| hydroperoxide<br/>peroxide
 +
|
 +
|-
 +
| R-5.5.6
 +
| hydropolysulfide<br/>polysulfide
 +
| and chalcogen analogues; "poly" is replaced by "di", "tri" etc.
 +
|-
 +
| R-5.5.7
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| sulfoxide<br/>sulfone<br/>selenoxide<br/>selenone
 +
|
 +
|-
 +
| R-5.6.2.1
 +
| ketone
 +
|
 +
|-
 +
| R-5.6.4.1
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| acetal<br/>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
 +
|-
 +
| R-5.6.6.2
 +
| hydrazone
 +
| functional modifier, added after name of carbonyl compound
 +
|-
 +
| R-5.6.6.3
 +
| azine
 +
| functional modifier, added after name of carbonyl compound
 +
|-
 +
| R-5.6.6.4
 +
| semicarbazone<br/>thiosemicarbazone<br/>selenosemicarbazone
 +
| functional modifier, added after name of carbonyl compound
 +
|-
 +
| R-5.7.4.2
 +
| ''see text''
 +
| for esters use name of anion
 +
|-
 +
| R-5.7.6
 +
| fluoride<br/>chloride<br/>bromide<br/>iodide
 +
| functional modifiers for acyl halides, added after name of acyl group
 +
|-
 +
| 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<br/>cyanate<br/>isocyanate<br/>fulminate<br/>thiocyanate<br/>isothiocyanate<br/>selenocyanate<br/>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==
 
==References==

Revision as of 18:12, 28 June 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
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
R-5.5.1.1 alcohol
R-5.5.1.2 mercaptan
selenol
tellurol 		no longer recommended
R-5.5.4.2 ether
sulfide
selenide
telluride
R-5.5.4.4 oxide functional modifier for oxiranes, added after name of alkene
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
R-5.6.2.1 ketone
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
R-5.6.6.2 hydrazone functional modifier, added after name of carbonyl compound
R-5.6.6.3 azine functional modifier, added after name of carbonyl compound
R-5.6.6.4 semicarbazone
thiosemicarbazone
selenosemicarbazone 		functional modifier, added after name of carbonyl compound
R-5.7.4.2 see text for esters use name of anion
R-5.7.6 fluoride
chloride
bromide
iodide 		functional modifiers for acyl halides, added after name of acyl group
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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