Photoelectron spectra of singly charged dicarboxylate anions HO2C(CH2)(n)CO2- (n = 1-10) are obtained at two different temperatures (300 and 70 K) at 193 nm. The electron binding energies of these species are observed to be much higher than the singly charged monocarboxylate anions, suggesting that the singly charged dicarboxylate anions are cyclic due to strong intramolecular hydrogen bonding between the terminal -CO2H and -CO2- groups. The measured electron binding energies are observed to depend on the chain length, reflecting the different -CO2H center dot center dot center dot-O2C-hydrogen bonding strength as a result of strain in the cyclic conformation. A minimum binding energy is found at n = 5, indicating that its intramolecular hydrogen bond is the weakest. At 70 K, all spectra are blue shifted relative to the room-temperature spectra with the maximum binding energy shift occurring at n = 5. These observations suggest that the cyclic conformation of HO2C(CH2)(5)CO2- (a ten-membered ring) is the most strained among the 10 anions. The present study shows that the -CO2H center dot center dot center dot-O2C- hydrogen bonding strength is different among the 10 anions and it is very sensitive to the strain in the cyclic conformations.