Next Article in Journal
Biogas Production from Physicochemically Pretreated Grass Lawn Waste: Comparison of Different Process Schemes
Previous Article in Journal
Considerations for Docking of Selective Angiotensin-Converting Enzyme Inhibitors
Previous Article in Special Issue
Tautomerism in Azo and Azomethyne Dyes: When and If Theory Meets Experiment
Open AccessArticle

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

1
Haute Ecole d’Ingénierie et d’Architecture Fribourg, HES-SO University of Applied Sciences of Western Switzerland, Pérolles 80, CH-1705 Fribourg, Switzerland
2
Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
3
Bulgarian Academy of Sciences, Institute of Organic Chemistry with Centre of Phytochemistry, Acad. G. Bonchev street, bl. 9, 1113 Sofia, Bulgaria
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(2), 298; https://doi.org/10.3390/molecules25020298
Received: 25 November 2019 / Revised: 16 December 2019 / Accepted: 27 December 2019 / Published: 11 January 2020
(This article belongs to the Special Issue Tautomerism and Proton Transfer Related Phenomena)
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: tautomerism; pinene derivatives; chiral ligands; molecular spectroscopy; theoretical description; keto-enol tautomerism; H-bonding tautomerism; pinene derivatives; chiral ligands; molecular spectroscopy; theoretical description; keto-enol tautomerism; H-bonding
MDPI and ACS Style

Solea, A.B.; Cornu, I.; Deneva, V.; Crochet, A.; Fromm, K.M.; Antonov, L.; Allemann, C.; Mamula, O. Tautomerism and Self-Association in the Solution of New Pinene-Bipyridine and Pinene-Phenanthroline Derivatives. Molecules 2020, 25, 298.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop