In chemistry, an onium ion is a cation formally obtained by the protonation of mononuclear parent hydride of a pnictogen (group 15 of the periodic table), chalcogen (group 16), or halogen (group 17). The oldest-known onium ion, and the namesake for the class, is ammonium, NH+4, the protonated derivative of ammonia, NH3.[1][2]
The name onium is also used for cations that would result from the substitution of hydrogen atoms in those ions by other groups, such as organic groups, or halogens; such as tetraphenylphosphonium, (C6H5)4P+. The substituent groups may be divalent or trivalent, yielding ions such as iminium and nitrilium.[1][2]
A simple onium ion has a charge of +1. A larger ion that has two onium ion subgroups is called a double onium ion, and has a charge of +2. A triple onium ion has a charge of +3, and so on.
Compounds of an onium cation and some other anion are known as onium compounds or onium salts.
Onium ions and onium compounds are inversely analogous to -ate ions and ate complexes:
- Lewis bases form onium ions when the central atom gains one more bond and becomes a positive cation.
- Lewis acids form -ate ions when the central atom gains one more bond and becomes a negative anion.[3]
- ^ a b Cite error: The named reference
IUPACwas invoked but never defined (see the help page). - ^ a b Cite error: The named reference
OlahBkwas invoked but never defined (see the help page). - ^ Advanced Organic Chemistry: Reactions and mechanisms, Maya Shankar Singh, 2007, Dorling Kindersley, ISBN 978-81-317-1107-1