Intramolecular general acid catalysis of the hydrolysis of 2-(2'-imidazolium)phenyl phosphate, and bond length-reactivity correlations for reactions of phosphate monoester monoanions |
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Authors: | Brandão Tiago A S Orth Elisa S Rocha Willian R Bortoluzzi Adailton J Bunton Clifford A Nome Faruk |
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Institution: | Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil. |
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Abstract: | Rate constants for the hydrolysis of 2-(2'-imidazolium)phenyl hydrogen phosphate (IMPP) in water at pH<6 indicate that activation by the imidazolium moiety disappears with the deprotonation of the phosphate group, and the reaction involves the hydrogen-bonding of the imidazolium NH with the aryl oxygen leaving group. The reaction should involve a near-planar conformation of the imidazolium and the phenyl groups in the activated complex, which favors proton-transfer. The crystal structure of IMPP was solved, and a bond length-reactivity correlation for reactions of phosphate monoester monoanions is described. |
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