Naslov
Solid and Solution State Structural Characterization of Thiosemicarbazone Derivatives: A Combined Experimental and Theoretical Study

Autori
Pičuljan, 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, ostalo

Izvornik
Program and Book of Abstracts / Smrečki, Vilko ; Vikić-Topić, Dražen - Zagreb : Institut Ruđer Bošković, 2014, 19-19

ISBN
978-953-7941-03-01

Skup
16th Central European NMR Symposium and 16th Central European Bruker NMR Users Meeting

Mjesto i datum
Zagreb, Hrvatska, 16.10.2014. - 17.10.2014

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
thiosemicarbazones; structure; hydrogen bonding; X-ray; NMR spectroscopy; conformational analysis

Sažetak
Thiosemicarbazones can exist in several tautomeric forms and conformations, with the possibility of intra- and intermolecular hydrogen bonding. Detailed structural characterization of thiosemicarbazones, as compounds that are associated with a wide spectrum of biological activities, is a prerequisite for better understanding of their bioactivity and for obtaining molecules with improved pharmacological properties. The aim of our research is to investigate the influence of substituents, the nature of the solvent (different polarity and different proton-donor and proton-acceptor abilities) and temperature on molecular conformation, tautomerism and nature of hydrogen bonding in salicylaldehyde and 2-methoxybenzaldehyde 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 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. Experimental results were complemented with computational research of conformational space in vacuum and organic solvents, by combination of molecular- and quantum-mechanical methods.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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