The nonexistence of repulsive 1,3-diaxial interactions in monosubstituted cyclohexanes

Hydrogen atoms directly involved in the so-called 1,3-syn-diaxial repulsion in the monosubstituted cyclohexanes studied here gain stabilization, giving evidence that this interaction is of an attractive nature and is not the origin of the generally observed equatorial preference that is usually accepted. Hydrogen and chlorine atoms and methyl and tert-butyl groups are more stable when they adopt the axial position in cyclohexane but produce the destabilization of the cyclohexyl ring. It is possible to conclude this from the analysis of the contribution of the atomic to the molecular energy determined in the frame of the theory of atoms in molecules. Electron transfer is responsible for this behavior as the charge distribution proves.