Theoretical study on the formation of a pentacyclo-undecane cage lactam

A quantum-chemical mechanistic investigation of the multistep mechanism of the one pot annular conversion of pentacyclo-undecane (PCU) cage lactam formation was carried out using density functional theory (DFT) level with the B3LYP hybrid functional in both the gas phase and with the self consistent reaction-field (SCRF) solvent model with the 6-31. +. G(d) basis set. The kinetic and thermodynamic properties of all species involved were investigated. The theoretical results suggest that the final product obtained is both thermodynamically and kinetically preferred. Moreover, the observed rate determining step compared favourably to the experimentally observed intermediate that was isolated before. © 2012 Elsevier B.V.