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{{short description|Chemical naming convention}}
{{see also|IUPAC nomenclature of organic chemistry|IUPAC nomenclature of inorganic chemistry}}▼
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<!-- In this article, several separate references of the ''Provisional Recommendations'' are given, because the complete pdf is difficult to read. -->
In [[chemical nomenclature]], a '''preferred IUPAC name''' ('''PIN''') is a unique name, assigned to a chemical substance and preferred among
Preferred IUPAC names are applicable only for [[organic compounds]], to which the IUPAC (International Union of Pure and Applied Chemistry) has the definition as compounds which contain at least a single carbon atom but no [[Alkali metal|alkali]], [[Alkaline earth metal|alkaline earth]] or [[transition metals]] and can be named by the nomenclature of organic compounds<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> (see [[#Scope_of_the_nomenclature_for_organic_compounds|below]]). Rules for the remaining organic and inorganic compounds are still under development.<ref>{{cite journal |last1=Hartshorn |first1=R. M. |last2=Hellwich |first2=K.-H. |last3=Yerin |first3=A. |last4=Damhus |first4=T. |last5=Hutton |first5=A. T. |title=Brief Guide to the Nomenclature of Inorganic Chemistry |journal=Pure and Applied Chemistry |date=2015 |volume=87 |issue=9–10 |pages=1039–1049 |doi=10.1515/pac-2014-0718 |s2cid=100897636 |access-date=20 February 2019 |url=https://iupac.org/cms/wp-content/uploads/2018/05/Inorganic-Brief-Guide-V1-3.pdf|hdl=10092/12053 |hdl-access=free }}</ref>
The concept of PINs is defined in the introductory chapter
== Definitions ==
▲{{
A '''preferred IUPAC name''' or '''PIN''' is a name that is preferred among two or more IUPAC names. An '''IUPAC name''' is a [[systematic name]] that meets the recommended IUPAC rules. IUPAC names include retained names. A '''general IUPAC name''' is any IUPAC name that is not a "preferred IUPAC name". A '''retained name''' is a traditional or otherwise often used name, usually a [[trivial name]], that may be used in IUPAC nomenclature.<ref name=Chapter1>IUPAC Provisional Recommendations 2004, par. 10-12, [http://old.iupac.org/reports/provisional/abstract04/BB-prs310305/Chapter1.pdf Chapter 1]</ref> ▼
▲A '''preferred IUPAC name''' or '''PIN''' is a name that is preferred among two or more IUPAC names. An '''IUPAC name''' is a [[Systematic_name#In_chemistry | systematic name]] that meets the recommended IUPAC rules. IUPAC names include retained names. A '''general IUPAC name''' is any IUPAC name that is not a "preferred IUPAC name". A '''retained name''' is a traditional or otherwise often used name, usually a [[trivial name]], that may be used in IUPAC nomenclature.<ref name=Chapter1>IUPAC Provisional Recommendations 2004, par.
Since systematic names often are not human-readable a PIN may be a retained name. Both "PINs" and "retained names" have to be chosen (and established by IUPAC) explicitly, unlike other IUPAC names, which automatically arise from IUPAC nomenclatural rules. Thus, the PIN is sometimes the retained name (e.g., phenol and acetic acid, instead of benzenol and ethanoic acid), while in other cases, the systematic name was chosen over a very common retained name (e.g., propan-2-one, instead of acetone).
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The systems of chemical nomenclature developed by the [[International Union of Pure and Applied Chemistry]] (IUPAC) have traditionally concentrated on ensuring that chemical names are unambiguous, that is that a name can only refer to one substance. However, a single substance can have more than one acceptable name, like [[toluene]], which may also be correctly named as "methylbenzene" or "phenylmethane". Some alternative names remain available as "retained names" for more general contexts. For example, [[tetrahydrofuran]] remains an unambiguous and acceptable name for the common organic solvent, even if the preferred IUPAC name is "oxolane".<ref>IUPAC Provisional Recommendations 2004, Rule P-53.2.2, [http://old.iupac.org/reports/provisional/abstract04/BB-prs310305/Chapter5.pdf Chapter5]</ref>
The nomenclature goes:<ref>IUPAC Provisional Recommendations 2004, P-51, [https://iupac.qmul.ac.uk/BlueBook/P5.html#510102 Chap P-5]</ref>
* Preselected names are to be used.
* [[Substitution reaction|Substitutive nomenclature]] (replacement of hydrogen atoms in the parent structure) is used most extensively, for example "ethoxyethane" instead of [[diethyl ether]] and "tetrachloromethane" instead of [[carbon tetrachloride]].
* [[Functional group|Functional class]] naming (also known as radicofunctional nomenclature) is preferred next. In the case of [[acid anhydride]]s, [[ester]]s, [[acyl halide]]s and pseudohalides and [[salt (chemistry)|salt]]s, this method takes precedence over substitution.
* [[Skeletal replacement]] ('a', named for the suffix), if it both applies and a heteroatom is found in a chain, is preferred over substitution. If it applies but no heteroatom is found in a chain, it is preferred over multiplicative nomenclature. Example: 3-phospha-2,5,7-trisilaoctane refers to CH<sub>3</sub>-SiH<sub>2</sub>-PH-CH<sub>2</sub>-SiH<sub>2</sub>-CH<sub>2</sub>-SiH<sub>2</sub>-CH<sub>3</sub>.
** Skeletal replacement mainly replaces carbon with other atoms, or in the case of [[phane nomenclature]], whole "superatom" rings. It also includes more complex replacements, such as the [[IUPAC nomenclature of inorganic chemistry 2005#Hydrides with non-standard bonding—lambda convention|lambda convention]].
* Multiplicative nomenclature is to be preferred over simple substitutive if it can be used. This is the nomenclature with an apostrophe after numbers such as 4'; it allows multiple occurrences of the principal characteristic group or compound class to be treated together. Example: 4,4′-sulfanediyldibenzoic acid refers to (COOH-C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>S.
The following are available, but not given special preference:<ref>IUPAC Provisional Recommendations 2004, P-51, [https://iupac.qmul.ac.uk/BlueBook/P5.html#510102 Chap P-5]</ref>
== Retained IUPAC names ==▼
* Conjunctive nomenclature is available, but substitutive, multiplicative, or skeletal should be preferred. Example: benzene-1,3,5-triacetic acid should instead be named 2,2′,2′′-(benzene-1,3,5-triyl)triacetic acid.
* Additive and subtractive operations remain available as with the general case. For example, one keeps changing "ane" into "ene" for double bonds. Additive operations generally have better names derived from the above rules, such as phenyloxirane for [[styrene oxide]].
{{Main|Retained name}}
The number of retained non-systematic, trivial names of simple organic compounds (for example [[formic acid]] and [[acetic acid]]) has been reduced considerably for preferred IUPAC names, although a larger set of retained names is available for general nomenclature. The traditional names of simple [[monosaccharides]], α-amino acids and many natural products have been retained as preferred IUPAC names; in these cases the systematic names may be very complicated and virtually never used. The name for [[water]] itself is a retained IUPAC name.
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== Notes and references ==
{{Reflist|
== Further reading ==
* {{cite book |last1=Wisniewski |first1=Janusz Leon |chapter=Chemical Nomenclature and Structure Representation: Algorithmic Generation and Conversion |title=Handbook of Chemoinformatics |date=5 May 2008 |pages=51–79 |doi=10.1002/9783527618279.ch4|isbn=978-3-527-30680-0 }} – background on why a preferred name is needed (multiple dialects of "systematic" such as [[Chemical Abstracts Service|CAS]] and [[Beilstein database |Beilstein]])
[[Category:Chemical nomenclature]]
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