Poly(acrylamidoximes) play an important role in the uranium extraction from seawater. The present work reports solution studies of simple analogues to address the formation and stability of two binding sites present in these polymers, open-chain amidoximes and cyclic imide dioximes, including: (1) conditions that maximize the formation of the cyclic form, (2) the existence of a base-induced conversion from open-chain to cyclic form, and (3) degradation under acid and base conditions.