Homoanomeric effect in the 1,2-dimethoxyethyl radical

A homoanomeric effect is found to stabilize the 1,2-dimethoxyethyl radical (CH3O-CH-CH2OCH3) in a conformation in which the singly-occupied orbital at the radical centre is approximately coplanar with the p-type lone pair on the a-oxygen and with the ß-C-O bond. The magnitude of this stabilization is predicted to be ~10-12 kJ mol-1 at the G3(MP2)-RAD and CBS-RAD levels of theory.