Atropisomeric xanthines: Synthesis, stereodynamics and absolute configuration

Perticarari, Sofia (2015) Atropisomeric xanthines: Synthesis, stereodynamics and absolute configuration. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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During the thesis period a new class of atropisomeric xanthine derivatives has been studied. We decided to focus our attention on these purine bases because of their various biological activities, that could play an important role in the discovery of new bioactive atropisomers. The synthesized compounds bear an Aryl-N chiral axis in position 1 of the xanthine scaffold, around which the rotation is prevented by the presence of bulky ortho substituents. Through a retro synthetic analysis we synthesized three atropisomeric structures bearing in position 1 of the purine scaffold respectively an o-tolyl, o-nitrophenyl and a 1-naphthyl group. The conformational studies by DFT simulations showed that the interconversion energy barrier between the two available skewed conformations is higher enough to obtain thermally stable atropisomers. After the separation of the atropisomers, the experimental energy of interconversion was investigated by means of kinetic studies following the thermal racemization process using an enantioselective HPLC column. The absolute configuration of each atropisomer was assigned by experimental ECD analysis and TD-DFT simulations of the ECD spectra.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Perticarari, Sofia
Relatore della tesi
Correlatore della tesi
Corso di studio
Parole chiave
xanthines circular dichroism NMR DFT calculations atropisomerism
Data di discussione della Tesi
24 Luglio 2015

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