The possible existence of the gas phase cis- and trans-maleate, i.e. completely deprotonated maleic acid (O2C–CΗ=CΗ–CO2)2–, is investigated by density functional (B3LYP) and ab-initio quantum chemical methods (MP2, CCSD(T)) using large basis sets. The calculations reveal that only the trans-isomer is Coulomb stable with respect to electron loss. The results are compared to other previously investigated dicarboxylate dianions of the general form −O2C–R–CO2 − with R = C2, C2X2, C2X4, and C6X4 (X = H, F). Fluorine substitution on the carbon framework helps to stabilize these doubly charged systems, and we predict that all of the aromatic fluorine substituted dicarboxylate dianions are Coulomb stable in the gas phase. Only the highest levels of theory reveal the slight stabilization of both the succinate dianion and the ortho-isomer of the phthalic acid dianion in unprecedented agreement with experiments.