Naslov
Structural Analysis of 2-Methoxybezaldehyde Thiosemicarbazone Derivatives : A Combined Experimental and Theoretical Study

Autori
Čuljak, Katarina ; Novak, Predrag ; Matković- Čalogović, Dubravka ; Petrina, Antonija , Šket, Primož ; Plavec, Janez ; Kodrin, Ivan ; Mihalić, Zlatko

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
3rd Annual East-NMR User Meeting / Mateja Vodiškar - Laško : Slovenian NMR Cenre, National Institute of Chemistry, 2012

ISBN
978-961-6104-21-0

Skup
3rd Annual East-NMR User Meeting

Mjesto i datum
Laško, Slovenija, 13.11.2012. - 16.11.2012

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
NMR ; thiosemicarbazones ; solid state ; solution

Sažetak
Thiosemicarbazones and their corresponding metal complexes are widely known compounds possessing diverse pharmacological activities, such as antitumor, antivirial, antibacterial, antifungal, antimalarial, etc. Bioactivity is closely related to molecular conformation which can significantly be affected by the presence of intra- and inter- molecular hydrogen bonds. Salicylaldehyde thiosemicarbazones can exist in several tautomeric forms with both intra- and inter-molecular hydrogen bonds. An intra- molecular O―H•••N H-bond between the hydroxyl group and the azomethine N atom has been found in salicylaldehyde thiosemicarbazone family (resonance assisted H- bond). Additionally, an intramolecular N―H •••N H- bond between the thiourea NH group and the azomethine N atom was found in few salicylaldehyde thiosemicarbazones. The aim of this research is to investigate the influence of substituents and solvents of different polarities on molecular conformation, tautomerism and structure of H-bonds in salicylaldehyde thiosemicarbazone derivatives. We present here a part of our study regarding the effect of substituting OH with OMe group in salycilaldehyde residue on the overall structure and thione-thiol tautomerism. Solid state structures of 1 (single polymorph) and 2 (two polymorphs) were characterized by single- crystal X-ray diffraction and high resolution 13C and 15N solid-state NMR spectroscopy. Since the crystal structure of 3 was reported previously, we employed 13C and 15N solid-state NMR experiments which provided structural data complementary to those obtained by X-ray diffraction. Solid state NMR parameters (15N, 13C) were used as a reference for solution study results. Possible solvent induced conformational and tautomeric equilibrium changes were probed by multinuclear (1H, 13C and 15N) temperature dependent NMR experiments in CDCl3 and DMSO solutions and quantum- mechanical calculations.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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