Computational methods for conformational analysis of unsymmetrical 1,3-diamines: 3-aminotropanes

Abstract

A comparative study has been performed to evaluate the ability of a range of computational theories to predict the relative basicity and the conformations of diamine systems. Specifically, molecular mechanics (MM3), semiempirical (AM1), and ab initio (Hartree–Fock) methods have been used in the conformational analyses of unprotonated, monoprotonated, and diprotonated 3-aminotropanes, a pair of isomeric 1,3-diamines. Use of the molecular mechanics force field, with the recently determined parameter set for protonated amines, affords results that are in agreement with experimental data, when corrected for water solvent (by setting the dielectric constant to 80). Ab initio and semiempirical calculations, in contrast, give inconsistent and incorrect results.