tertiarybutylammonium

tert-Butylammonium refers to a cation with the chemical formula (CH3)3CNH3+. It is the protonated form of tert-butylamine. This cation is typically encountered as a salt, where it pairs with various anions. For instance, tert-butylammonium bromide, (CH3)3CNH3+Br-, is a common example.

Tert-butylammonium salts find application in organic synthesis. They can act as phase-transfer catalysts, facilitating reactions between reagents in immiscible phases. The bulky tert-butyl group can influence solubility and reactivity. In some contexts, tert-butylammonium ions are used as counterions in the preparation of metal complexes or ionic liquids, where their specific steric and electronic properties are advantageous.

The stability of the tert-butylammonium cation is moderate. Like other ammonium ions, it can be deprotonated by strong bases to regenerate the parent amine, tert-butylamine. The tert-butyl group, being a tertiary alkyl group, imparts steric hindrance around the nitrogen atom. This steric bulk can affect the kinetic and thermodynamic aspects of reactions involving the cation. The synthesis of tert-butylammonium salts usually involves the reaction of tert-butylamine with the corresponding acid.