Electron density analysis of small ring ethers

Atoms in molecules theory (AIM) was employed to compute the atomic properties for a series of five protonated and neutral oxacycloalkanes (CH2)nO (n=2–6), on B3LYP/6-311++G(2d,2p) electron distributions. Atomic energies indicate that strain of oxacycloalkanes results from a destabilization of oxygen and hydrogens that is not compensated for by the stabilization of cyclic carbons. Atomic electron populations point out that cycloalkyloxonium cations are better described by an O–H+ structure than by the widespread use of the O+–H structure.