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New chiral Schiff base-zinc complexes and their esterolytic catalytic activity
A new series of chiral Zn-Schiff base (imine) complexes has been prepared from mono-N-sulfonyl derivatives of (1R,2R)-diaminocyclohexane, N-heterocyclic aldehydes, and zinc salts. The formation and characterization of the (L)ZnX 2 complexes was established by NMR, IR and HRESI-MS. Spectroscopic and kinetic evidence indicates that these ligands may be bidentate or tridentate depending on conditions of the medium. The methanolysis of a chiral, racemic picolinate ester catalyzed by the Zn(II)-Schiff base complexes was studied kinetically. The rate constants were found to vary approximately a hundred-fold and in a complex way depending on the imine ligand and the Zn-counter anion, kobs = 5.0 ¡Á 10-6-4.8 ¡Á 10-4 M -1 s-1. A Job plot analysis of ternary complex formation of LZnX2 with two phosphonate transition state analogs suggests that two types of (imine)Zn(picolinate)X ternary complexes may be intermediates and that varying rate-limiting steps may be involved in the LZnX2- catalyzed methanolysis of picolinate esters.
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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI