Catalytic hydrolysis of phosphate esters by metallocomplexes of 1,10-Phenanthroline derivatives in micellar solution

John G.J. Weijnen, Johan F.J. Engbersen

    Research output: Contribution to journalArticleAcademicpeer-review

    24 Citations (Scopus)

    Abstract

    Divalent metal‐ion complexes of 2,9‐bis[(methyldodecylamino)methyl]‐1,10‐phenanthroline (C12Phen—MII) in neutral Brij 35 micelles catalyse the hydrolysis of various phosphate triesters, diesters and monoesters. The catalytic activity of C12Phen—MII has been compared with that of the metal‐ion complexes of its water‐soluble counterpart 2,9‐bis[(dimethyl‐amino)methyl]‐1,10‐phenanthroline (C1Phen—MII). Saturation kinetics provide evidence for preliminary formation of ligand‐MII‐phosphate ester complexes, which decay to products. The hydrolysis of diphenyl 4‐nitrophenyl phosphate (1b) coordinated to C12Phen—ZnII proceeds 8700 times faster than the hydrolysis of 1b in the absence of metallocatalyst. Kinetic studies indicate that phosphate triesters containing a metal‐ion‐binding site in close proximity to the phosphoryl bond, i.e., diphenyl 5‐nitro‐2‐pyridyl phosphate (2b) and diphenyl 5‐nitro‐8‐quinolyl phosphate (3), are hydrolysed by the same mechanism as 1b.
    Original languageEnglish
    Pages (from-to)351-357
    JournalRecueil des travaux chimiques des Pays-Bas
    Volume112
    Issue number6
    DOIs
    Publication statusPublished - 1993

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