Vi. Kadentsev et al., REACTIVITY OF MOLECULES WITH NITROGEN-CONTAINING FUNCTIONAL-GROUPS TOWARD H+ AND SIME3+ IONS, Russian chemical bulletin, 47(6), 1998, pp. 1228-1229
The equilibrium constants of trimethylsilyl cation transfer reactions
differ from those of proton transfer reactions by many orders of magni
tude. The basicity of MeCN (1), MeNO2 (2), and Et2NH (3) in the gas ph
ase decreases in the series 3 >> 1 > 2, whereas the affinity of the sa
me compounds for trimethylsilyl cation decreases in the series 1 >> 3
approximate to 2. Semiempirical quantum-chemical MNDO calculations ind
icate that the formation of MeCN . SiMe3+ ions is thermodynamically mo
re favorable than that of MeNH2SiMe3+ ions.