Molecular orbital study of gas phase basicities of carbofunctional derivatives of group IVB elements; stereochemical control

The gas phase basicities of a series of carbofunctional derivatives H₃M(CH₂)_nX (M = C, Si, Ge; X = NH₂, OH, F; n = 1–3) were investigated by the semiempirical CNDO/2 method. The calculations indicate that the electronic effects of silyl- and germyl-substituents differ greatly from the effect of simple alkyls. Moreover, in contrast to simple carbon derivatives, the overall nature of the electronic effects of siliyl- and germyl-substituents is crucially influenced by the molecular conformation.