Theoretic
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Tetraalkylammonium metal
For a long time I have been thinking about such a thing as tetraalkylammonium metals. Tetramethylammonium metal (TMA metal) in particular. Did you
wonder what happens if you give electrons to TMA ions in equal quantity? Would it just become a very active alkali-style metal? Sodium metal is Na+
ions floating in an electron sea, TMA metal similarly. Although there can be a Na atom, with the electron going into orbit, the TMA ion doesn't
have aspare space for an electron and so the TMA metal should be a much stronger reducer. Tetraalkylammonium metals with ethyl, propyl and butyl
groups for the alkyl part should find use in applications like photoelements that need a very active, loosely bonded to its electrons alkali metal.
Do you think these can form? If so, I see three posible ways of making them:
1) Electrolysis (well, duh! When everything else fails, try electrolysis, although I don't know an application where electrolysis is
indispensable and cannot be substituted by chemical methods) of a tetraalkylammonium (TAA) salt.
2) Decomposition of a TAA azide.
3) Reduction of a solution of a TAA chloride in liquid ammonia with sodium. Sodium chloride precipitates, then you can filter that and evaporate the
ammonia, leaving you with your TAA metal of choice.
What d'ya say? 
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JohnWW
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Unfortunately, pentavalent compounds of N can can have only four covalent bonds plus an ionic bond. This means that the product of electrolysis of a
tetraalkylammonium salt cannot result in a stable discharged product at the cathode utilizing the cation; it would decompose to a tertiary amine. With
Na metal and the chloride in liquid ammonia, you would probably end up with either the tetraalkylammonium salt of electrons solvated in NH3, or its
amide, plus NaCl and NaNH2.
John W.
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Theoretic
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No, I don't mean (CH3)5N! I mean (CH3)4N+ e-, in analogy with Na+ e- (sodium metal). Yes, it will be four covalent bonds and one ionic (to the
electron).
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