Journal article

Tautomerism and self-association in the solution of new pinene-bipyridine and pinene-phenanthroline derivatives

  • Solea, Atena B. Haute Ecole d’Ingénierie et d’Architecture Fribourg, HES-SO University of Applied Sciences of Western Switzerland, Pérolles 80, CH-1705 Fribourg, Switzerland - Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
  • Cornu, Ivan Haute Ecole d’Ingénierie et d’Architecture Fribourg, HES-SO University of Applied Sciences of Western Switzerland, Pérolles 80, CH-1705 Fribourg, Switzerland
  • Deneva, Vera Bulgarian Academy of Sciences, Institute of Organic Chemistry with Centre of Phytochemistry, Acad. G. Bonchev street, bl. 9, 1113 Sofia, Bulgaria
  • Crochet, Aurélien Haute Ecole d’Ingénierie et d’Architecture Fribourg, HES-SO University of Applied Sciences of Western Switzerland, Pérolles 80, CH-1705 Fribourg, Switzerland
  • Fromm, Katharina M. Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
  • Antonov, Liudmil Bulgarian Academy of Sciences, Institute of Organic Chemistry with Centre of Phytochemistry, Acad. G. Bonchev street, bl. 9, 1113 Sofia, Bulgaria
  • Allemann, Christophe Haute Ecole d’Ingénierie et d’Architecture Fribourg, HES-SO University of Applied Sciences of Western Switzerland, Pérolles 80, CH-1705 Fribourg, Switzerland
  • Mamula, Olimpia Haute Ecole d’Ingénierie et d’Architecture Fribourg, HES-SO University of Applied Sciences of Western Switzerland, Pérolles 80, CH-1705 Fribourg, Switzerland
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    11.01.2020
Published in:
  • Molecules. - 2020, vol. 25, no. 2, p. 298
English 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.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/308599
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