Homoanomeric Effect in the 1,2-Dimethoxyethyl Radical

Abstract

A homoanomeric effect is found to stabilize the 1,2-dimethoxyethyl radical (CH₃O–ĊH–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 α-oxygen and with the β-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.