Chemical nomenclature

A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC).

The IUPAC's 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 "color books" are supplemented by shorter recommendations for specific circumstances which are published from time to time in the journal Pure and Applied Chemistry.

Aims of chemical nomenclature

The primary function of chemical nomenclature is to ensure that a spoken or written chemical name leaves no ambiguity as to what chemical compound the name refers: each chemical name should refer to a single substance. A less important aim is to ensure that each substance has a single name, although the number of acceptable names is limited.

Preferably, the name also conveys some information about the structure or chemistry of a compound. CAS numbers form an extreme example of names that do not perform this function: each CAS number refers to a single compound but none contain information about the structure.

The form of nomenclature used depends on the audience to which it is addressed. As such, no single correct form exists, but rather there are different forms that 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 (InChI)—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.

Differing aims of lexicography and chemical nomenclature

It is generally understood that the aims of normal English lexicography versus chemical nomenclature vary and are to an extent at odds. Dictionaries of English words on the web or otherwise collect and report the meanings of words as their uses appear and change over time. Chemical nomenclature on the other hand (with IUPAC nomenclature as the best example) is necessarily more restrictive: it aims to standardize communication and practice so that when a chemical term is used, it has a fixed meaning relating to chemical structure, and thereby, can give insights into chemical properties and derived molecular functions. These differing aims can have profound effects on valid understanding in chemistry, especially with regard to chemical classes made popular for perceived health benefits; this is particularly true in the new media age of the web, where word meanings can rapidly change. A discussion related to the term polyphenol is a clear example (where various web definitions and common uses of the word are at odds with its chemical nomenclature, which connects polyphenol structure and bioactivity).

History

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.

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

Main article: IUPAC nomenclature of 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

Main article: IUPAC nomenclature of inorganic chemistry

Compositional nomenclature

Examples of compositional names are:

• PCl₅ phosphorus pentachloride
• N₂O₄ dinitrogen tetraoxide

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 or international 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), oxidane (H₂O), 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(III) chloride

Note that ligands such as chloride become chlorido- rather than chloro- as in substitutive naming.

See also

• IUPAC nomenclature of inorganic chemistry 2005
• IUPAC nomenclature of organic chemistry
• Preferred IUPAC name
• IUPAC numerical multiplier
• IUPAC nomenclature for organic transformations
• International Chemical Identifier
• List of chemical compounds with unusual names

References

1. ^ Nomenclature of Organic Chemistry (3rd ed.), London: Butterworths, 1971 [1958 (A: Hydrocarbons, and B: Fundamental Heterocyclic Systems), 1965 (C: Characteristic Groups)], ISBN 0408701447 .
2. ^ International Union of Pure and Applied Chemistry (1979). Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H. Oxford: Pergamon. ISBN 0-08022-3699. . IUPAC, the Blue Book; Oxford: Blackwell Science (1993). ISBN 0-632-03488-2. Online edition: [1]. . International Union of Pure and Applied Chemistry (2004). Nomenclature of Organic Chemistry (IUPAC Provisional Recommendations 2004). .
3. ^ International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. Electronic version..
4. ^ International Union of Pure and Applied Chemistry (1993). Quantities, Units and Symbols in Physical Chemistry, 2nd edition, Oxford: Blackwell Science. ISBN 0-632-03583-8. Electronic version..
5. ^ Compendium of Chemical Terminology, IMPACT Recommendations (2nd Ed.), Oxford:Blackwell Scientific Publications. (1997)
6. ^ Biochemical Nomenclature and Related Documents, London:Portland Press, 1992.
7. ^ International Union of Pure and Applied Chemistry (1998). Compendium of Analytical Nomenclature (definitive rules 1997, 3rd. ed.). Oxford: Blackwell Science. ISBN 0-86542-6155. .
8. ^ Compendium of Macromolecular Nomenclature, Oxford:Blackwell Scientific Publications, 1991.
9. ^ Compendium of Terminology and Nomenclature of Properties in Clinical Laboratory Sciences, IMPACT Recommendations 1995, Oxford: Blackwell Science, ISBN 0-86542-6120 .
10. ^ Guyton de Morveau, L. B. (1782), J. Phys. 19: 310 .
11. ^ Guyton de Morveau, L. B.; Lavoisier, A. L.; Berthollet, C. L.; Fourcroy, A. F. de (1787), Méthode de Nomenclature Chimique, Paris: Cuchet, http://imgbase-scd-ulp.u-strasbg.fr/displayimage.php?album=692&pos=3 .
12. ^ Lavoisier, A. L. (1801), Traité Élémentaire de Chimie (3e ed.), Paris: Deterville .
13. ^ Berzelius, J. J. (1811), J. Phys. 73: 248 .
14. ^ Wisniak, Jaime (2000), "Jöns Jacob Berzelius A Guide to the Perplexed Chemist", Chem. Educator 5 (6): 343–50, doi:10.1007/s00897000430a .
15. ^ "Congrès de nomenclature chimique, Genève 1892", Bull. Soc. Chim. Paris, Ser. 3 7: xiii–xxiv, 1892, http://gallica.bnf.fr/ark:/12148/bpt6k2820064.image .

External links

• Interactive IUPAC Compendium of Chemical Terminology (interactive "Gold Book")
• 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)
• chemicalize.org A free web site/service that extracts IUPAC names from web pages and annotates a 'chemicalized' version with structure images. Structures from annotated pages can also be searched.
• ChemAxon Name <> Structure - IUPAC (& traditional) name to structure and structure to IUPAC name software. As used at chemicalize.org
• ACD/Name - Generates IUPAC, INDEX (CAS), InChi, Smiles, etc. for drawn structures in 10 languages and translates names to structures. Also available as batch tool and for Pipeline Pilot. Part of I-Lab 2.0