The abstraction of a proton by OH,- O-2(-), and XO2- from DMEn center dot center dot center dot X+, where X is Li, Na, or K, is studied using density functional theory. Both the gas phase and the solution phase are studied. In general, when explicit solvent molecules are added, the difference between the gas-phase and solution results becomes rather small. While the DMEn center dot center dot center dot X+ binding energies differ significantly for various alkali cations, the reaction energies and transition-state energies are far less sensitive to the choice of an alkali cation. XO2- has a lower barrier height than OH-, which, in turn, has a lower barrier height than O-2(-). The reaction energies follow the same trends.