A theoretical study of epibatidine

Abstract

A theoretical study of the conformational profile of epibatidine and its protonated form has been carried out using molecular mechanics (CVFF and CFF91), semiempirical (AM1) and ab initio (RHF/6-31G* and B3LYP/6-31G*) methods. Six minima have been found for the neutral molecule and four for the protonated one with small rotational barriers between them. The stability of the minima has been explained using the AIM methodology. Finally, the NMR shieldings of the different conformers found have been calculated with the GIAO method and used to assign some of the ambiguous experimental signals.