Polydentate N,O-Ligands Possessing Unsymmetrical Urea Fragments Attached to a p-Cresol Scaffold

In this study, three series of polydentate N,O-ligands possessing unsymmetrical urea fragments attached to a p-cresol scaffold are obtained, namely mono- and bi-substituted open-chain aromatics, synthesised using a common experiment, as well as fused aryloxazinones. Separate protocols for the prepar...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-09, Vol.28 (18), p.6540
Main Authors: Todorova, Stanislava E., Rusew, Rusi I., Shivachev, Boris L., Kurteva, Vanya B.
Format: Article
Language:English
Subjects:
Chloride
Efficiency
fused aryloxazinones
Geometry
Hydrocarbons
Hydrogen bonds
ITC
Ligands
NMR
polydentate N,O-ligands
Solvents
unsymmetrical urea
XRD
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Summary:In this study, three series of polydentate N,O-ligands possessing unsymmetrical urea fragments attached to a p-cresol scaffold are obtained, namely mono- and bi-substituted open-chain aromatics, synthesised using a common experiment, as well as fused aryloxazinones. Separate protocols for the preparation of each series are developed. It is found that in the case of open-chain compounds, the reaction output is strongly dependent on both bis-amine and carbamoyl chloride substituents, while oxazinones can be effectively obtained via a common protocol. The products are characterized via 1D and 2D NMR spectra in solution and using single-crystal XRD. A preliminary study on the coordination abilities of the products performed via ITC shows that there are no substantial interactions in the pH range of 5.0–8.5 in general.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28186540