Application of the lanthanide shift reagent Eu(fod), to a series of benzylideneanilines causes isomerhation of the stable trans form to the less stable cis form. A linear relationship was obtained between the %cis isomer with the mole ratio of Eu(fod)$substrate.
The 13C chemical shifts of cis-and trans-benzylidenepropylamine and substituted benzylideneanilines were analysed after additons of Eu(fod),. The cisltrans ratio increases as the amount of lanthanide shift reagent increased. The cis isomers showed large lanthanide-induced shifts, whereas the trans isomers showed little or no effect.
The equilibrium constants of charge transfer complexes (CTC) of salicylidene amino pyridines and salicylidene aniline with lanthanide shift reagent Eu(fod) 3 in different solvents were determined by applying Benesi-Hildebrand equation. The effect of the polarity of the solvent, electronic factors and steric effect were investigated.Structural and energetic parameters like bond lengths, bond angles, energies of HOMO and LUMO orbitals, η, µ, and ω were obtained by quantum mechanical calculations employing semi empirical model (Austin Method1, AM1) and an abinitio method represented by Hartree Fock (HF) at base set level 6-311G(d,p).
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