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Phenylenediamine derivatives of dehydroacetic acid: synthesis, characterisation and deuterium isotope effects (CROSBI ID 627570)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa

Jednačak, Tomislav ; Novak, Predrag ; Užarević, Krunoslav ; Bratoš, Igor ; Marković, Jelena ; Cindrić, Marina Phenylenediamine derivatives of dehydroacetic acid: synthesis, characterisation and deuterium isotope effects // Pharma NMR Conference: Application of NMR Spectroscopy in Pharmaceutical Industry : Programme & Book of Abstracts / Novak, Predrag ; Tomišić, Vladislav ; Bregović, Nikola (ur.). Zagreb: International Association of Physical Chemists (IAPC), 2015. str. 27-27

Podaci o odgovornosti

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

engleski

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

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.

dehydroacetic acid ; synthesis ; structure characterisation ; deuterium isotope effects

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Podaci o prilogu

27-27.

2015.

objavljeno

Podaci o matičnoj publikaciji

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)

Podaci o skupu

Pharma NMR Conference : Application of NMR Spectroscopy in Pharmaceutical Industry

poster

23.09.2015-25.09.2015

Rovinj, Hrvatska

Povezanost rada

Kemija