Moving towards Nitrogen-Based Lewis Acids: A Theoretical Study

摘要

Density functional calculations predict that reduction of heteroatom in cyclic nitrenium ion increases the Lewis acidity. Calculations also predict that annelation is a very effective way of stabilizing cyclic nitrenium ions and increasing the Lewis acidic character at the nitrenium centre. This is supported by the lowering in the energies of LUMO coupled with the high values of electrophilicity index as well as high hydride affinity. Substituents are also likely to influence their Lewis acidity. Electron withdrawing substituents increases their acidity while electron donating substituents decreases the same.