Hydrogen chloride Complex with trimethylamine

The trimethylamine complex is stable to water, methanol, and hydrogen chloride at room temperature. Heating with HCl in a sealed tube leads to the uptake of two molecules of the hydrogen halide, suggesting formation of an ionic product (53). 

Borane, which is used as a complex with tetrahydrofuran [992] or dimethyl sulfide [611, 992] or generated in situ from lithium borohydride with boron trifluoride etherate [646] or sodium borohydride with aluminum chloride [184], reacts with 3 mol of an alkene to form a tertiary borane. The oxidation with alkaline hydrogen peroxide [183, 992, 1201] or with trimethylamine oxide [991, 992] yields an alcohol (equations 598 and 599). 

We now turn our attention of hydrogen-bonded complexes of HCl with ammonia and trimethylamine. Direct combination of gaseous ammonia and hydrogen chloride results in the formation of solid ammonium chloride, (NH4)+C1 . The crystal structure of (ND4)C1 at 5 K has been determined by neutron diffraction [18], The ammonium ions are found to be perfectly tetrahedral with N-D bond distances of 103 pm. Each of them is surrounded by eight chloride ions at the corners of a cube, with N- Cl distances of 382 pm. The cations are oriented in such a manner that the four N-D bonds are pointing towards alternating comers of the cube formed by the anions. This means that the coordination geometry of the H atoms is linear with H- Cl distances of 279 pm. 

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