IUPAC system and IUPAC rules of naming of nitriles

Nitriles contain a carbon - nitrogen triple bond (R-CºN or R-CN). They are indirectly related to amides (by the loss of H2O from a primary amide), and react chemically similar to carboxylic acids and their derivatives. It should be noted that H-CºN is not truly a nitrile and is named hydrogen cyanide.

When a nitrile group is the highest priority functional group present in the molecule, it is named as an alkanenitrile (alkenenitrile, alkynenitrile, ...). Since the -CºN must occur at the end of a chain of carbon atoms, the carbon of the nitrile will be carbon 1 in the numbering scheme. Other functional groups are located by this numbering scheme. Since the nitrile group is always at carbon number 1, there is no need to indicate its' location.

Examples naming simple nitriles:

Compound Name
Line Drawing
3D Model
cyclobutyronitrile *
pentanedinitrile **

* note: the -yl is changed to a -yro.
** note: numbers are not needed as the nitriles must be at the ends of the chain.

Examples naming more complex nitriles:

Compound Name
Line Drawing

1 comment:

tpatter said...

CN is a functional group and is NOT part of the parent chain-its attached to that longest chain.
NC-CH2-CH2-CN is ethane-1,2-dicarbonitrile not butane1,4-dinitrile