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, k(obs) =5.0 x 10(-6)-4.8 x 10(-4) M(-1) s(-1). A Job plot analysis of ternary complex formation of LZnX(2) 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 LZnX(2)-catalyzed methanolysis of picolinate esters. (C) 2011 Elsevier B.V. All rights reserved.