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| − | '''IUPAC | + | '''IUPAC nomenclature''' is a system of naming [[chemical compound]]s and of describing the science of [[chemistry]] in general. It is developed and kept up to date under the auspices of the [[International Union of Pure and Applied Chemistry]] (IUPAC). |
| − | The rules for naming [[Organic compound|organic]] and [[inorganic compound]]s are contained in two publications, known as the ''[[Nomenclature of Organic Chemistry|Blue Book]]''<ref>{{citation | title = Nomenclature of Organic Chemistry | origyear = 1958 (A: Hydrocarbons, and B: Fundamental Heterocyclic Systems), 1965 (C: Characteristic Groups) | year =1971 | edition = 3rd | publisher = Butterworths | location = London | isbn = 0408701447}}.</ref><ref name="bluebook">{{BlueBook1979}}. {{BlueBook1993}}. {{BlueBook2004}}.</ref> and the ''[[Nomenclature of Inorganic Chemistry|Red Book]]''<ref name="redbook">{{RedBook2005}}.</ref> respectively. A third publication, known as the ''[[Quantities, Units and Symbols in Physical Chemistry|Green Book]]'',<ref name="greenbook">{{GreenBook2nd}}.</ref> describes the recommendations for the use of [[symbol]]s for [[Physical quantity|physical quantities]] (in association with the [[IUPAP]]), while a fourth, the ''[[Compendium of Chemical Terminology|Gold Book]]'',<ref name="goldbook"> | + | The rules for naming [[Organic compound|organic]] and [[inorganic compound]]s are contained in two publications, known as the ''[[Nomenclature of Organic Chemistry|Blue Book]]''<ref>{{citation | title = Nomenclature of Organic Chemistry | origyear = 1958 (A: Hydrocarbons, and B: Fundamental Heterocyclic Systems), 1965 (C: Characteristic Groups) | year =1971 | edition = 3rd | publisher = Butterworths | location = London | isbn = 0408701447}}.</ref><ref name="bluebook">{{BlueBook1979}}. {{BlueBook1993}}. {{BlueBook2004}}.</ref> and the ''[[Nomenclature of Inorganic Chemistry|Red Book]]''<ref name="redbook">{{RedBook2005}}.</ref> respectively. A third publication, known as the ''[[Quantities, Units and Symbols in Physical Chemistry|Green Book]]'',<ref name="greenbook">{{GreenBook2nd}}. {{GreenBook3rd}}</ref> describes the recommendations for the use of [[symbol]]s for [[Physical quantity|physical quantities]] (in association with the [[IUPAP]]), while a fourth, the ''[[Compendium of Chemical Terminology|Gold Book]]'',<ref name="goldbook">{{GoldBook2nd}}.</ref> contains the definitions of a large number of technical terms used in chemistry. Similar compendia exist for [[biochemistry]]<ref name="biochem">{{WhiteBook2nd}}.</ref> (the ''White Book'', in association with the [[IUBMB]]), [[analytical chemistry]]<ref name="anal">{{OrangeBook3rd}}.</ref> (the ''[[Compendium of Analytical Nomenclature|Orange Book]]''), [[macromolecular chemistry]]<ref name="macro">{{PurpleBook}}.</ref> (the ''Purple Book'') and [[clinical chemistry]]<ref>{{SilverBook}}.</ref> (the ''Silver Book''). These "colour books" are supplemented by shorter recommendations for specific circumstances which are published from time to time in the [[Scientific journal|journal]] ''[[Pure and Applied Chemistry]]''. |
This article treats the system of nomenclature in general, notably its aims and historical development. Separate articles treat the naming of [[IUPAC nomenclature of organic chemistry|organic compounds]] and [[IUPAC nomenclature of inorganic chemistry|inorganic compounds]] in more detail. | This article treats the system of nomenclature in general, notably its aims and historical development. Separate articles treat the naming of [[IUPAC nomenclature of organic chemistry|organic compounds]] and [[IUPAC nomenclature of inorganic chemistry|inorganic compounds]] in more detail. | ||
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A common name will often suffice to identify a chemical compound in a particular set of circumstances. To be more generally applicable, the name should indicate at least the [[chemical formula]]. To be more specific still, the three-dimensional arrangement of the atoms may need to be specified. | A common name will often suffice to identify a chemical compound in a particular set of circumstances. To be more generally applicable, the name should indicate at least the [[chemical formula]]. To be more specific still, the three-dimensional arrangement of the atoms may need to be specified. | ||
| − | In a few specific circumstances (such as the construction of large indices), it becomes necessary to ensure that each compound has a unique name: this requires the addition of extra rules to the standard IUPAC system (the [[ | + | In a few specific circumstances (such as the construction of large indices), it becomes necessary to ensure that each compound has a unique name: this requires the addition of extra rules to the standard IUPAC system (the [[CAS nomenclature|CAS system]] is the most commonly used in this context), at the expense of having names which are longer and less familiar to most readers. Another system gaining popularity is the [[International Chemical Identifier]]—while InChI symbols are not human-readable, they contain complete information about substance structure. That makes them more general than CAS numbers. |
The IUPAC system is often criticized for the above failures when they become relevant (for example in differing reactivity of sulfur [[allotropes]] which IUPAC doesn't distinguish). While IUPAC has a human-readable advantage over CAS numbering, it would be difficult to claim that the IUPAC names for some larger, relevant molecules (such as [[rapamycin]]) are human-readable, and so most researchers simply use the informal names. | The IUPAC system is often criticized for the above failures when they become relevant (for example in differing reactivity of sulfur [[allotropes]] which IUPAC doesn't distinguish). While IUPAC has a human-readable advantage over CAS numbering, it would be difficult to claim that the IUPAC names for some larger, relevant molecules (such as [[rapamycin]]) are human-readable, and so most researchers simply use the informal names. | ||
== History == | == History == | ||
| − | [[ | + | [[File:Lavoisier nomenclature.gif|right|thumb|First page of Lavoisier's ''Chymical Nomenclature'' in English.]] |
The nomenclature of [[alchemy]] is rich in description, but does not effectively meet the aims outlined above. Opinions differ whether this was deliberate on the part of the early practitioners of alchemy or whether it was a consequence of the particular (and often esoteric) theoretical framework in which they worked. | The nomenclature of [[alchemy]] is rich in description, but does not effectively meet the aims outlined above. Opinions differ whether this was deliberate on the part of the early practitioners of alchemy or whether it was a consequence of the particular (and often esoteric) theoretical framework in which they worked. | ||
| Line 32: | Line 32: | ||
== Types of nomenclature == | == Types of nomenclature == | ||
===Organic chemistry=== | ===Organic chemistry=== | ||
| − | *Substitutive name | + | *[[Substitutive nomenclature|Substitutive name]] |
| − | *Functional class name, also known as a radicofunctional name | + | *[[Functional class nomenclature|Functional class name]], also known as a radicofunctional name |
| − | *Conjunctive name | + | *[[Conjunctive nomenclature|Conjunctive name]] |
| − | *Additive name | + | *[[Additive nomenclature|Additive name]] |
| − | *Subtractive name | + | *[[Subtractive nomenclature|Subtractive name]] |
| − | *Multiplicative name | + | *[[Multiplicative nomenclature|Multiplicative name]] |
| − | *Fusion name | + | *[[Fusion nomenclature|Fusion name]] |
*[[Hantzsch–Widman nomenclature|Hantzsch–Widman name]] | *[[Hantzsch–Widman nomenclature|Hantzsch–Widman name]] | ||
| − | *Replacement name | + | *[[Replacement nomenclature|Replacement name]] |
===Inorganic chemistry=== | ===Inorganic chemistry=== | ||
====Compositional nomenclature==== | ====Compositional nomenclature==== | ||
| − | Examples of compositional names are: | + | Examples of [[Compositional nomenclature|compositional names]] are: |
* PCl<sub>5</sub> [[phosphorus pentachloride]] | * PCl<sub>5</sub> [[phosphorus pentachloride]] | ||
* Ca<sub>2</sub>P<sub>3</sub> dicalcium triphosphide | * Ca<sub>2</sub>P<sub>3</sub> dicalcium triphosphide | ||
| Line 63: | Line 63: | ||
==References== | ==References== | ||
| − | {{reflist}} | + | {{reflist|2}} |
== External links == | == External links == | ||
| Line 74: | Line 74: | ||
* [http://www.chem.qmul.ac.uk/iupac/ IUPAC Recommendations on Organic & Biochemical Nomenclature, Symbols, Terminology, etc.] (includes IUBMB Recommendations for biochemistry) | * [http://www.chem.qmul.ac.uk/iupac/ IUPAC Recommendations on Organic & Biochemical Nomenclature, Symbols, Terminology, etc.] (includes IUBMB Recommendations for biochemistry) | ||
| − | [[Category:Chemical nomenclature]] | + | [[Category:Chemical nomenclature|*IUPAC]] |
{{Imported from Wikipedia|name=IUPAC nomenclature|id=327289937}} | {{Imported from Wikipedia|name=IUPAC nomenclature|id=327289937}} | ||
Latest revision as of 17:37, 17 October 2010
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC). The rules for naming organic and inorganic compounds are contained in two publications, known as the Blue Book[1][2] and the Red Book[3] respectively. A third publication, known as the Green Book,[4] describes the recommendations for the use of symbols for physical quantities (in association with the IUPAP), while a fourth, the Gold Book,[5] contains the definitions of a large number of technical terms used in chemistry. Similar compendia exist for biochemistry[6] (the White Book, in association with the IUBMB), analytical chemistry[7] (the Orange Book), macromolecular chemistry[8] (the Purple Book) and clinical chemistry[9] (the Silver Book). These "colour books" are supplemented by shorter recommendations for specific circumstances which are published from time to time in the journal Pure and Applied Chemistry.
This article treats the system of nomenclature in general, notably its aims and historical development. Separate articles treat the naming of organic compounds and inorganic compounds in more detail.
Contents
Aims of chemical nomenclature
The primary function of chemical nomenclature is to ensure that the person who hears or reads a chemical name is under no ambiguity as to which chemical compound it refers to: each name should refer to a single substance. It is considered less important to ensure that each substance should have a single name, although the number of acceptable names is limited.
It is also preferable that the name convey some information about the structure or chemistry of a compound. CAS numbers form an extreme example of names which do not perform this function: each refers to a single compound but none contain information about the structure.
The form of nomenclature which should be used depends on the public to which it is addressed: as such there is no single correct form, but rather different forms which are more or less appropriate in different circumstances.
A common name will often suffice to identify a chemical compound in a particular set of circumstances. To be more generally applicable, the name should indicate at least the chemical formula. To be more specific still, the three-dimensional arrangement of the atoms may need to be specified.
In a few specific circumstances (such as the construction of large indices), it becomes necessary to ensure that each compound has a unique name: this requires the addition of extra rules to the standard IUPAC system (the CAS system is the most commonly used in this context), at the expense of having names which are longer and less familiar to most readers. Another system gaining popularity is the International Chemical Identifier—while InChI symbols are not human-readable, they contain complete information about substance structure. That makes them more general than CAS numbers.
The IUPAC system is often criticized for the above failures when they become relevant (for example in differing reactivity of sulfur allotropes which IUPAC doesn't distinguish). While IUPAC has a human-readable advantage over CAS numbering, it would be difficult to claim that the IUPAC names for some larger, relevant molecules (such as rapamycin) are human-readable, and so most researchers simply use the informal names.
History
The nomenclature of alchemy is rich in description, but does not effectively meet the aims outlined above. Opinions differ whether this was deliberate on the part of the early practitioners of alchemy or whether it was a consequence of the particular (and often esoteric) theoretical framework in which they worked.
While both explanations are probably valid to some extent, it is remarkable that the first "modern" system of chemical nomenclature appeared at the same time as the distinction (by Lavoisier) between elements and compounds, in the late eighteenth century.
The French chemist Louis-Bernard Guyton de Morveau published his recommendations[10] in 1782, hoping that his "constant method of denomination" would "help the intelligence and relieve the memory". The system was refined in collaboration with Berthollet, de Fourcroy and Lavoisier,[11] and promoted by the latter in a textbook which would survive long after his death at the guillotine in 1794.[12] The project was also espoused by Jöns Jakob Berzelius,[13][14] who adapted the ideas for the German-speaking world.
The recommendations of Guyton covered only what would be today known as inorganic compounds. With the massive expansion of organic chemistry in the mid-nineteenth century and the greater understanding of the structure of organic compounds, the need for a less ad hoc system of nomenclature was felt just as the theoretical tools became available to make this possible. An international conference was convened in Geneva in 1892 by the national chemical societies, from which the first widely accepted proposals for standardization arose.[15]
A commission was set up in 1913 by the Council of the International Association of Chemical Societies, but its work was interrupted by World War I. After the war, the task passed to the newly formed International Union of Pure and Applied Chemistry, which first appointed commissions for organic, inorganic and biochemical nomenclature in 1921 and continues to do so to this day.
Types of nomenclature
Organic chemistry
- Substitutive name
- Functional class name, also known as a radicofunctional name
- Conjunctive name
- Additive name
- Subtractive name
- Multiplicative name
- Fusion name
- Hantzsch–Widman name
- Replacement name
Inorganic chemistry
Compositional nomenclature
Examples of compositional names are:
- PCl5 phosphorus pentachloride
- Ca2P3 dicalcium triphosphide
An alternative method uses the oxidation state on the metal in place of suffices, e.g.:
- SnCl2, tin(II) chloride as an alternative to tin dichloride.
Generally this system, known as Stock nomenclature, is preferred over the prefix system for ionic compounds.
Substitutive nomenclature
This naming method generally follows established IUPAC organic nomenclature. Hydrides of the main group elements (groups 13–17) are given -ane base names, e.g. borane, BH3, phosphane, PH3 (the name phosphine is also in common use, but is not recommended by IUPAC). The compound PCl3 would be named substitutively as trichlorophosphane.
Additive nomenclature
This naming method has been developed principally for coordination compounds although it can be more widely applied. An example of its application is:
- [CoCl(NH3)5]Cl2 pentaamminechloridocobalt(2+) chloride
Note that ligands such as chloride become chlorido- rather than chloro- as in substitutive naming.
See also
References
- ↑ Nomenclature of Organic Chemistry, 3rd ed.; Butterworths: London, 1971. ISBN 0408701447.
- ↑ Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H; IUPAC Recommendations 1979; Pergamon: Oxford, 1979. ISBN 0-08022-369-9, <http://www.acdlabs.com/iupac/nomenclature/>. A Guide to IUPAC Nomenclature of Organic Compounds; IUPAC Recommendations 1993; Blackwell Science: Oxford, 1993. ISBN 0-632-03488-2, <http://www.acdlabs.com/iupac/nomenclature/>. Nomenclature of Organic Chemistry; IUPAC Provisional Recommendations 2004; IUPAC, 2004, <http://old.iupac.org/reports/provisional/abstract04/favre_310305.html>.
- ↑ Nomenclature of Inorganic Chemistry; IUPAC Recommendations 2005; Royal Society of Chemistry: Cambridge, 2005. ISBN 0-85404-438-8, <http://www.iupac.org/publications/books/rbook/Red_Book_2005.pdf>.
- ↑ Quantities, Units and Symbols in Physical Chemistry, 2nd ed.; Blackwell Science: Oxford, 1993. ISBN 0-63203-5838, <http://old.iupac.org/publications/books/gbook/green_book_2ed.pdf>. Quantities, Units and Symbols in Physical Chemistry, 3rd ed.; Royal Society of Chemistry: Cambridge. ISBN 0-85404-433-7
- ↑ Compendium of Chemical Terminology; IUPAC Recommendations; Blackwell Science: Oxford. ISBN 0-86542-6848, <http://www.iupac.org/publications/compendium/index.html>.
- ↑ Biochemical Nomenclature and Related Documents, 2nd ed.; IUPAC–IUBMB Recommendations; Portland Press: London. ISBN 1-85578-005-4, <http://www.chem.qmw.ac.uk/iupac/bibliog/white.html>.
- ↑ Compendium of Analytical Nomenclature, 3rd ed.; IUPAC Definitive Rules 1997; Blackwell Science: Oxford. ISBN 0-86542-6155, <http://www.iupac.org/publications/analytical_compendium/>.
- ↑ Compendium of Macromolecular Nomenclature; Blackwell Science: Oxford. ISBN 0-63202-8475, <http://www.iupac.org/publications/books/author/metanomski.html#ct>.
- ↑ Compendium of Terminology and Nomenclature of Properties in Clinical Laboratory Sciences; IUPAC Recommendations 1995; Blackwell Science: Oxford. ISBN 0-86542-6120.
- ↑ Guyton de Morveau, L. B. J. Phys. 1782, 19, 310.
- ↑ Guyton de Morveau, L. B.; Lavoisier, A. L.; Berthollet, C. L.; Fourcroy, A. F. de Méthode de Nomenclature Chimique; Cuchet: Paris, 1787, <http://imgbase-scd-ulp.u-strasbg.fr/displayimage.php?album=692&pos=3>.
- ↑ Lavoisier, A. L. Traité Élémentaire de Chimie, 3e ed.; Deterville: Paris, 1801.
- ↑ Berzelius, J. J. J. Phys. 1811, 73, 248.
- ↑ Wisniak, Jaime Jöns Jacob Berzelius A Guide to the Perplexed Chemist. Chem. Educator 2000, 5 (6), 343–50. DOI: 10.1007/s00897000430a.
- ↑ Congrès de nomenclature chimique, Genève 1892. Bull. Soc. Chim. Paris, Ser. 3 1892, 7, xiii–xxiv, <http://gallica.bnf.fr/ark:/12148/bpt6k2820064.image>.
External links
- IUPAC Nomenclature Books Series (list of all IUPAC nomenclature books, and means of accessing them)
- IUPAC Compendium of Chemical Terminology ("Gold Book")
- Quantities, Units and Symbols in Physical Chemistry ("Green Book")
- IUPAC Nomenclature of Organic Chemistry ("Blue Book")
- Nomenclature of Inorganic Chemistry IUPAC Recommendations 2005 ("Red Book")
- IUPAC Recommendations on Organic & Biochemical Nomenclature, Symbols, Terminology, etc. (includes IUBMB Recommendations for biochemistry)
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