The Synthesis and Structural Characterization of Peralkylated Triguanide Superbases

Abstract

Organic superbases derived from a peralkylated triguanide framework have been synthesized in a coupling reaction between monosubstituted guanidines and a Vilsmeier salt. Single crystal X-ray diffraction analysis of the chloride salt allowed the structural characterization of the benzyl derivative for the first time and revealed an effective delocalization of the positive charge despite significant distortion of the triguanide cation planarity. With the calculated gas phase basicity ranging from 262 to 265 kcal mol–1 and pKa values in acetonitrile between 28 and 30, these compounds have been evaluated as potential organocatalysts in the transesterification reaction of vegetable oil.