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• W2435561938 endingPage "6464" @default.
• W2435561938 startingPage "6449" @default.
• W2435561938 abstract "Bidentate enantiopure Schiff base ligands, (R or S)-N-1-(Ar)ethyl-2-oxo-1-naphthaldiminate (R- or S-N^O), diastereoselectively provide Λ- or Δ-chiral-at-metal four-coordinated Zn(R- or S-N^O)2 {Ar = C6H5; Zn-1R or Zn-1S and p-C6H4OMe; Zn-2R or Zn-2S}. Two R- or S-N^O-chelate ligands coordinate to the zinc(II) in a tetrahedral mode and induce Λ- or Δ-configuration at the zinc metal center. In the solid state, the R- or S-ligand diastereoselectively gives Λ- or Δ-Zn configuration, respectively, and forms enantiopure crystals. Single crystal structure determinations show two symmetry-independent molecules (A and B) in each asymmetric unit to give Z′ = 2 structures. Electronic circular dichroism (ECD) spectra show the expected mirror image relationship resulting from diastereomeric excess toward the Λ-Zn for R-ligands and Δ-Zn for S-ligands in solution. ECD spectra are well reproduced by TDDFT calculations, while the application of the exciton chirality method, in the common point-dipole approximation, predicts the wrong sign for the long-wavelength couplet. A dynamic diastereomeric equilibrium (Λ vs Δ) prevails for both R- and S-ligand–metal complexes in solution, respectively, evidenced by 1H NMR spectroscopy. Variable temperature 1H NMR spectra show a temperature-dependent shift of the diastereomeric equilibrium and confirm Δ-Zn configuration (for S-ligand) to be the most stable one and favored at low temperature. DSC analyses provide quantitative diastereomeric excess in the solid state for Zn-2R and Zn-2S, which is comparable to the results of solution studies." @default.
• W2435561938 created "2016-06-24" @default.
• W2435561938 creator A5001332862 @default.
• W2435561938 creator A5010758104 @default.
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• W2435561938 creator A5047280172 @default.
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• W2435561938 creator A5069725359 @default.
• W2435561938 creator A5090644272 @default.
• W2435561938 creator A5091370930 @default.
• W2435561938 date "2016-06-13" @default.
• W2435561938 modified "2023-10-16" @default.
• W2435561938 title "Synthesis, X-ray, and Spectroscopic Study of Dissymmetric Tetrahedral Zinc(II) Complexes from Chiral Schiff Base Naphthaldiminate Ligands with Apparent Exception to the ECD Exciton Chirality" @default.
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