Naslov
Phenylenediamine derivatives of dehydroacetic acid: synthesis, characterisation and deuterium isotope effects

Autori
Jednačak, Tomislav ; Novak, Predrag ; Užarević, Krunoslav ; Bratoš, Igor ; Marković, Jelena ; Cindrić, Marina

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

Izvornik
Pharma NMR Conference: Application of NMR Spectroscopy in Pharmaceutical Industry : Programme & Book of Abstracts / Novak, Predrag ; Tomišić, Vladislav ; Bregović, Nikola - Zagreb : International Association of Physical Chemists (IAPC), 2015, 27-27

Skup
Pharma NMR Conference: Application of NMR Spectroscopy in Pharmaceutical Industry

Mjesto i datum
Crveni Otok, Rovinj, Hrvatska, 23.09.2015. - 25.09.2015

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
dehydroacetic acid ; synthesis ; structure characterisation ; deuterium isotope effects

Sažetak
Dehydroacetic acid, (3-acetyl-4-hydroxy-6-methyl- 2H-pyran-2-dione) is a biologically active molecule with antifungal and antimicrobial properties. Enaminones derived from dehydroacetic acid have a great potential as bioactive compounds, too. They can exist in two different tautomeric forms: keto- amine and hydroxy-imine. Three phenylenediamine derivatives of dehydroacetic acid have been synthesised and their structures determined by a combined use of NMR and IR spectroscopies and mass spectrometry. Structure analysis pointed towards the localised keto-amine form as the dominant tautomeric form in solution and solid-state. Relatively broad N–H stretching bands observed in IR spectra and significant N–H proton down-field and keto C=O up-field shifts in NMR spectra indicated the presence of intra- molecular hydrogen bonds in all investigated compounds. In order to gain further insight into the nature of these interactions in solution, deuterated isotopomers have been prepared and deuterium isotope effects in 13C NMR spectra have been determined and analysed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA