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Naming Nitriles
Definition of nitriles:
Nitriles
are organic chemical compounds that include the functional group -C≡N
That is, nitriles are a class or category of chemical compounds that include a nitrogen atom connected to a carbon atom by a triple covalent bond.
Nitrile molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms. |
Names of Nitriles in General
Many chemicals and categories of chemicals have been known by different (general, and specific) names in the past.
Nitriles used to be known as cyanides.
This page indicates the modern names, chemical structures, and some of the previous and less common names of some simple nitriles. It is useful to know and recognise previous and unusual names of nitriles but when naming nitriles in coursework and exam questions the modern names of nitriles are generally expected.
The smallest chemical whose molecular structure includes a nitrogen atom connected to a carbon atom by a triple covalent bond is hydrogen cyanide (HCN), whose structure may be drawn as simply: H-C≡N .
However, because HCN does not include a carbon chain (of at least two carbon atoms linked together) it does not always count as a true "organic molecule".
For this reason lists of linear nitriles usually start with ethanenitrile, as shown below.
Names and Structures of simple Linear Nitriles
The homologous series of simple linear nitriles with the -nitrile group (i.e. a single nitrogen atom attached to a carbon atom by a triple covalent bond) attached to the first (=last!) carbon atom is shown below for carbon chain lengths of up to 10 carbon atoms:
Number carbons in chain |
Name |
Simple Structure |
Previous / Other Names
*Examples; not complete lists!
(Not required for A-Level) |
and simple formula |
showing bond types but not accurate bond angles |
 |
2 |
|
 |
- Acetonitrile
- Cyanomethane
- Methyl cyanide
- Ethanenitrile
- Ethyl nitrile
- Methanecarbonitrile
- Acetonitril
- Ethanonitrile
- Methylkyanid
- Ethane nitrile
|
3 |
|
 |
- n-Propanenitrile
- Ethyl cyanide
- Propionitrile
- Propiononitrile
- Propylnitrile
- Cyanoethane
- Hydrocyanic ether
- Propionic nitrile
- Ethylkyanid
- Propannitril
|
4 |
butanenitrile |
CH3CH2CH2CN |
|
 |
- n-Butanenitrile
- Butyronitrile
- n-Butyronitrile
- Propyl cyanide
- n-Propyl cyanide
- Butyrylonitrile
- 1-Cyanopropane
- Butane nitrile
- Propylkyanid
- Butyric acid nitrile
|
5 |
pentanenitrile |
CH3CH2CH2CH2CN |
|
 |
- n-Pentanenitrile
- Butyl cyanide
- 1-Butyl cyanide
- Valeronitrile
- n-Valeronitrile
- 1-Cyanobutane
|
6 |
hexanenitrile |
CH3CH2CH2CH2CH2CN |
|
 |
- Hexanonitrile
- Capronitrile
- n-Capronitrile
- Tricapronile
- Pentyl cyanide
- 1-Cyanopentane
- Amyl Cyanide
- n-Amyl cyanide
|
7 |
heptanenitrile |
CH3CH2CH2CH2CH2CH2CN |
|
 |
- n-Heptanenitrile
- Heptanonitrile
- Hexyl cyanide
- Enanthonitrile
- 1-Cyanohexane
- Heptane nitrile
- Heptane-1-nitrile
|
8 |
octanenitrile |
CH3CH2CH2CH2CH2CH2CH2CN |
|
 |
- Heptyl cyanide
- Octanonitrile
- Caprylonitrile
- Caprylnitrile
- Arneel 8
- 1-Cyanoheptane
|
9 |
nonanenitrile |
CH3CH2CH2CH2CH2CH2CH2CH2CN |
|
 |
- Nonanitrile
- Nonanonitrile
- n-Octyl cyanide
- n-Nonanonitrile
- n-Octylcyanide
- Octyl cyanide
- 1-Cyanooctane
- n-Nonanenitrile
|
10 |
decanenitrile |
CH3CH2CH2CH2CH2CH2CH2CH2CH2CN |
 |
|
 |
- n-Decanenitrile
- Nonyl cyanide
- Caprinitrile
- Decanonitrile
- 1-Cyanononane
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Why stop at ten carbon atoms (in the chain) ? It doesn't ... there are more similar linear nitriles. We stopped here due to page width !
Important Note: *The synonyms indicated for compounds listed above are just some examples of alternative names found online and believed to have been used to refer to the substance indicated. They have not all been verified and may include common (non-scientific) names, trade names specific to particular suppliers, and perhaps errors. The purpose of these lists is to give a general indication of the range of names by which nitriles are known - both generally, and specifically.
See also the related page about functional groups in organic molecules, which includes the nitrile group among others.
Note:
This is one of many pages about types of organic compounds in our Organic Chemistry Section. Similar and related pages describe hydrocarbons, alkanes, haloalkanes, alkenes, alkynes, cycloalkanes, aromatic hydrocarbons (arenes), alcohols, esters, ethers, aldehydes, ketones, carboxylic acids, acid chlorides, acid anhydrides, azo dyes, amines, amides, nitriles, amino acids (chemistry), peptides, proteins (chemistry), polypeptides and others. If you need further information ask your chemistry tutor.
According to the International Union of Pure and Applied Chemistry (IUPAC) recommendations for nomenclature of organic chemistry, compounds with the general structure -C≡N are called nitriles (and sometimes cyanides) and may be named substitutively in a manner similar to that for acids and other related compounds, see more about naming nitriles at http://www.acdlabs.com/iupac/nomenclature/93/r93_557.htm.
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