In this project, two new tridentate ketoimines were synthesized and utilized to prepare a series of magnesium, zinc, and aluminum complexes which were characterized spectroscopically and crystallographically. The Schiff base condensation synthetic reaction of 8-aminoquinoline with 2-acetylcyclopentanone yielded two different ketoimines reflecting quinolyl addition to the carbonyl of the cyclopentanone ring and the carbonyl of the acetyl functional group. Both ketoimines were isolated and the major product was characterized crystallographically. The major product ketoimine was used to prepared magnesium, zinc, and aluminum complexes with a variety of synthetic methodologies yielding bis-ligated homoleptic complexes as well as ketoimine phenoxide complexes. The complexes were characterized spectroscopically as well as with single crystal x-ray crystallography. Cyclopentanone ring flexibility varied among the complexes yielding both simple and complex 1H-1H coupling patterns observed in the 1H NMR spectra. Crystallographic analysis showed various coordination numbers and geometries and both mononuclear and dimeric structures. The collection of complexes offers many opportunities for comparison of bond lengths and bond angles. Time-Dependent Density Functional Theory calculations were used to map the electronic structures for the series of complexes and ketoimines and provide insight into the nature of the observed electronic transitions.

Synthesis and characterization of tridentate ketoimines and their use in preparation of a series of magnesium, zinc, and aluminum complexes

ACS Spring 2022

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