Naslov
NMR and quantum chemical studies of hydrogen bonding in acetylacetone and benzoylacetone derived enaminones

Autori
Jednačak, Tomislav ; Lazić, Vedrana ; Jurković, Mihaela ; Hrenar, Tomica ; Parlov Vuković, Jelena ; Novak, Predrag

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

Izvornik
Program and book of abstracts / Smrečki, Vilko ; Vikić-Topić, Dražen - Zagreb : Institut Ruđer Bošković, 2014, 16-16

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
enaminones; hydrogen bonding; NMR spectroscopy; quantum chemical studies

Sažetak
Enaminones represent an important class of organic molecules with interesting biological properties, such as anticonvulsant, antimicrobial, antioxidant, antitumor and cytogenetic activity. They might exist in two tautomeric forms: keto-amine and enol- imine. The structure and hydrogen bonding of acetylacetone and benzoylacetone derived enaminones in DMSO and CDCl3 solutions have been studied by a combination of NMR spectroscopy and quantum chemical (PM6 and DFT) methods. It has been demonstrated that the investigated compounds mainly existed in the localised keto-amine tautomeric form. Down-field chemical shifts of NH and OH protons and significant line-broadening have clearly indicated that both groups formed hydrogen bonds, which has further been supported by quantum chemical calculations. Concentration and temperature dependent NMR measurements have shown that amine protons are involved in strong intramolecular hydrogen bonding of the NH•••O=C type in both solvents. On the other hand, hydroxyl protons are engaged in weaker intermolecular hydrogen bonds with solvent molecules in DMSO, while in chloroform intermolecular interactions between two molecules are dominant. The presented results can further be used for better understanding and exploiting properties these compounds possess, especially their bioactivity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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