Structural and electronic effects on the reactivity of carbamoylsilanes towards acrylonitrile addition

The effect of substituents on Si and N on t1/2 values in the addition of carbamoylsilanes to acrylonitrile was explored. After examination of steric and structural parameters, the best correlation was found to be that rates increased with a decrease in the ionization potential of the carbamoylsilane.

The rates of addition to acrylonitrile of a series of carbamoylsilanes were found to increase with an increase in the size of alkyl groups attached to silicon and nitrogen. X-ray structural parameters indicated that steric compression within the carbamoylsilanes was not a factor in determining reactivity, but the ionization potentials of the carbamoylsilanes roughly paralleled the reactivity pattern observed.Figure optionsDownload as PowerPoint slide