Tautomerism and Self-Association in the Solution of New Pinene-Bipyridine and Pinene-Phenanthroline Derivatives

Solea, Atena B. (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland ; University of Fribourg, Fribourg, Switzerland) ; Cornu, Ivan (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Deveva, Vera (Bulgarian Academy of Sciences, Sofia, Bulgaria) ; Crochet, Aurélien (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Fromm, Katharina M. (University of Fribourg, Fribourg, Switzerland) ; Antonov, Liudmil (Bulgarian Academy of Sciences, Sofia, Bulgaria) ; Allemann, Christophe (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Mamula Steiner, Olimpia (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland)

Two novel pinene-type ligands have been synthesized and their tautomeric and self-associating behavior studied in solution and in the solid state. The first ligand, an acetylated derivative of 5,6-pinene-bipyridine, displays keto-enol tautomerism in solution. This tautomeric equilibrium was studied by NMR and UV-Vis spectroscopy in various solvents, and the results were compared with the ones obtained through DFT calculations. The second ligand was obtained by an unusual oxidation of the phenanthroline unit of a pinene-phenanthroline derivative. This compound exists as a single tautomer in solution and aggregates both in solution (as observed by NMR) and in the solid state through H-bonding as observed by X-ray structure determination and confirmed by DFT studies.


Keywords:
Article Type:
scientifique
Faculty:
Ingénierie et Architecture
School:
HEIA-FR
Institute:
ChemTech - Institut des technologies chimiques
Date:
2020-01
Pagination:
13 p.
Published in:
Molecules
Numeration (vol. no.):
2020, vol. 25, no. 5, article no. 298
DOI:
ISSN:
1420-3049
Appears in Collection:



 Record created 2021-01-15, last modified 2021-01-20

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