Bioactive Phenylenediamine Derivatives of Dehydroacetic Acid: Synthesis, Structural Characterization and Deuterium Isotope Effects

• DOI: 10.5562/cca1825
• Publication Date: 2011-10-05T07:51:53Z
• Authors: Tomislav Jednačak; Predrag Novak; Krunoslav Užarević; Igor Bratoš; Jelena Marković; Marina Cindrić
• Keywords: Dehydroacetic acid; Characterization

Several phenylenediamine derivatives of dehydroacetic acid, 3-acetyl-4-hydroxy-6-methyl-2Hpyran-2-one have been synthesized and their structure elucidated by using NMR IR spectroscopies mass spectrometry.Spectral analyses pointed toward the localized keto-amine form as predominant tautomeric in solution solid-state which was agreement with X-ray data.The relatively broad N-H stretching bands observed spectra significant proton down-field keto C=O up-field shifts indicated presence intra-molecular hydrogen bonds all studied compounds.In order to gain further insights into nature these interactions deuterated isotopomers prepared deuterium isotope effects 13 C determined analyzed.The magnitude sign confirmed existence bonds.Observed differences reflected different bond dynamics compounds.The results presented this paper might help better understanding biological properties related compounds.(