Correlating Structure and KA2 Catalytic Activity of ZnII Hydrazone Complexes

Two new Zn(II) complexes bearing tridentate hydrazone‐based ligands with NNO or NNS donor atoms were synthesised and characterised by elemental analysis, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopies, and single crystal X‐ray diffraction methods. These complexes, together with fo...

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Published inEuropean journal of inorganic chemistry Vol. 26; no. 33
Main Authors Adejumo, Temiloluwa T., Danopoulou, Marianna, Zorba, Leandros P., Pevec, Andrej, Zlatar, Matija, Radanović, Dušanka, Savić, Milica, Gruden, Maja, Anđelković, Katarina K., Turel, Iztok, Čobeljić, Božidar, Vougioukalakis, Georgios C.
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 24.11.2023
Subjects
Alkynes
Catalytic activity
Chemical analysis
Chemical reactions
Density Functional Theory
Electronic structure
Hydrazones
Infrared analysis
Inorganic chemistry
ketone-amine-alkyne coupling reaction
Ketones
Ligands
NMR
Nuclear magnetic resonance
Organic chemistry
Schiff bases
Single crystals
XRD
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Summary:Two new Zn(II) complexes bearing tridentate hydrazone‐based ligands with NNO or NNS donor atoms were synthesised and characterised by elemental analysis, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopies, and single crystal X‐ray diffraction methods. These complexes, together with four previously synthesised analogues, having hydrazone ligands with a NNO donor set of atoms, were successfully employed as catalysts in the ketone‐amine‐alkyne (KA2) coupling reaction, furnishing tetrasubstituted propargylamines, compounds with unique applications in organic chemistry. DFT calculations at the CAM‐B3LYP/TZP level of theory were performed to elucidate the electronic structure of the investigated Zn(II) complexes, excellently correlating the structure of the complexes to their catalytic reactivity. In this manuscript, the synthesis, characterization, and crystal structures of ZnII complexes bearing hydrazone ligands are described. The complexes were evaluated as possible catalysts in the ketone‐amine‐alkyne coupling reaction. Insights into the catalytic activity of the ZnII complexes were obtained by electronic structure investigations, using DFT calculations.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.202300193