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Tetraethylammonium
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Tetraethylammonium
Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula [(CH3CH2)4N]+, consisting of four ethyl groups (−CH2CH3 or −C2H5, often abbreviated as −Et) attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily crystallized and more toxic.
Tetraethylammonium is a potassium channel blocker. It inhibits the return to the resting potential of action potentials in neurons by binding to the voltage-gated potassium channels in nerve cell membranes and blocking the passage of potassium ions (responsible for the repolarization of an action potential) out of the neuron.
The halide salt is prepared by the reaction of triethylamine and an ethyl halide:
This method works well for the preparation of tetraethylammonium iodide (where X = I).
Most tetraethylammonium salts are prepared by salt metathesis reactions. For example, the synthesis of tetraethylammonium perchlorate, a salt that has been useful as a supporting electrolyte for polarographic studies in non-aqueous solvents, is carried out by mixing the water-soluble salts tetraethylammonium bromide and sodium perchlorate in water, from which the water-insoluble tetraethylammonium perchlorate precipitates:
Other examples include tetraethylammonium cyanide ([(CH3CH2)4N]+CN−), and trichlorostannate ([(CH3CH2)4N]+[SnCl3]−). In some cases, salts are produced of anions that cannot be generated in water, such as tetraethylammonium tetrachloronickelate(II) salt ([(CH3CH2)4N]+)2[NiCl4]2−, with the tetrahedral [NiCl4]2− anion.
The principal chemical characteristic of tetraethylammonium salts is their ability to engage in processes involving phase-transfer, such as phase-transfer catalysis. Typically, the four ethyl groups surrounding the nitrogen are too small to facilitate efficient ion transfer between aqueous and organic phases, but tetraethylammonium salts have been found to be effective in a number of such applications, and these are exemplified under the headings of the individual salts.
TEA salts such as tetraethylammonium tetrafluoroborate and tetraethylammonium methylsulfonate are used in supercapacitors as organic electrolytes.
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Tetraethylammonium
Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula [(CH3CH2)4N]+, consisting of four ethyl groups (−CH2CH3 or −C2H5, often abbreviated as −Et) attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily crystallized and more toxic.
Tetraethylammonium is a potassium channel blocker. It inhibits the return to the resting potential of action potentials in neurons by binding to the voltage-gated potassium channels in nerve cell membranes and blocking the passage of potassium ions (responsible for the repolarization of an action potential) out of the neuron.
The halide salt is prepared by the reaction of triethylamine and an ethyl halide:
This method works well for the preparation of tetraethylammonium iodide (where X = I).
Most tetraethylammonium salts are prepared by salt metathesis reactions. For example, the synthesis of tetraethylammonium perchlorate, a salt that has been useful as a supporting electrolyte for polarographic studies in non-aqueous solvents, is carried out by mixing the water-soluble salts tetraethylammonium bromide and sodium perchlorate in water, from which the water-insoluble tetraethylammonium perchlorate precipitates:
Other examples include tetraethylammonium cyanide ([(CH3CH2)4N]+CN−), and trichlorostannate ([(CH3CH2)4N]+[SnCl3]−). In some cases, salts are produced of anions that cannot be generated in water, such as tetraethylammonium tetrachloronickelate(II) salt ([(CH3CH2)4N]+)2[NiCl4]2−, with the tetrahedral [NiCl4]2− anion.
The principal chemical characteristic of tetraethylammonium salts is their ability to engage in processes involving phase-transfer, such as phase-transfer catalysis. Typically, the four ethyl groups surrounding the nitrogen are too small to facilitate efficient ion transfer between aqueous and organic phases, but tetraethylammonium salts have been found to be effective in a number of such applications, and these are exemplified under the headings of the individual salts.
TEA salts such as tetraethylammonium tetrafluoroborate and tetraethylammonium methylsulfonate are used in supercapacitors as organic electrolytes.
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