| Abstract
| - Rate constants for the hydrolysis of 2-(2‘-imidazolium)phenyl hydrogen phosphate (IMPP) in water atpH < 6 indicate that activation by the imidazolium moiety disappears with the deprotonation of thephosphate group, and the reaction involves the hydrogen-bonding of the imidazolium NH with the aryloxygen leaving group. The reaction should involve a near-planar conformation of the imidazolium andthe phenyl groups in the activated complex, which favors proton-transfer. The crystal structure of IMPPwas solved, and a bond length−reactivity correlation for reactions of phosphate monoester monoanionsis described.
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