A METALLOMICELLE CATALYZED-HYDROLYSIS OF A PHOSPHATE TRIESTER, A PHOSPHONATE DIESTER AND O-ISOPROPYL METHYLFLUOROPHOSPHONATE (SARIN)

A metallomicelle based on the copper(II) complex of N,N,N'-trimethyl-N '-tetradecylethylenediamine is shown to be an excellent catalyst for t he hydrolysis of 2,4-dinitrophenyl diethyl phosphate (DNPDEP), 2,4-din itrophenyl ethyl methylphosphonate (DNPEMP) and O-isopropyl methylfluo rophosphonate (Sarin), At pH 8 and 35 degrees C the hydrolysis of DNPD EP is accelerated by 1.3 x 10(5) fold, while that of of DNPEMP is incr eased by 6.6 x 10(4) fold, The micelle is also an active catalyst for the hydrolysis of the nerve agent Sarin, A mechanism involving binding of the phosphoryl oxygen to copper(II) and intramolecular attack by c oordinated hydroxide at the phosphorus centre is consistent with the k inetic data. (C) 1998 Elsevier Science S.A. All rights reserved.