The mass spectra of three tetraalkylammonium bromide salts and two series of bistetraalkylammonium bromide salts, one saturated and the other unsaturated, have been studied. Substitution is the major process which occurs in the pyrolytic decomposition of these quaternary ammonium bromides when placed in the probe of the mass spectrometer. This leads to the production of a tertiary amine and an alkyl halide. The substitution reactions which occur are influenced by the proximity of the bromide anion(s) to the positively charged quaternary nitrogen centers in the crystal lattice. As well, a shorter distance between the positive nitrogen centers favors substitution reaction by means of an electron inductive effect.
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Verrall et al. (1974) studied this question.