Original title: Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
Authors: Procházková, Eliška ; Čechová, Lucie ; Žurek, Jiří ; Janeba, Zlatko ; Dračínský, Martin
Document type: Papers
Conference/Event: Symposium on Chemistry of Nucleic Acid Components /16./, Český Krumlov (CZ), 2014-06-08 / 2014-06-13
Year: 2014
Language: eng
Abstract: The formation of strong intramolecular hydrogen bonds was observed in a series of 2-amino-5-nitrosopyrimidines with alkylamino and arylamino substituents in the positions 4 and 6. Mixtures of two rotamers differing in the orientation of the nitroso group were observed in the NMR spectra of the compounds where two distinct intramolecular hydrogen bonds could be formed. In several cases, we were able to isolate and characterize the two hydrogen bond isomers (two conformers) by column chromatography. The ratio of the two rotamers in equilibrium depends strongly on the character of the substituents in the positions 4 and 6 and can be finely tuned in a broad range of conformation ratios. The experimental results were supported by DFT calculations.
Keywords: intramolecular hydrogen bonds; NMR spectroscopy; polysubstituted 5-nitrosopyrimidines
Project no.: GA13-24880S (CEP)
Funding provider: GA ČR
Host item entry: Chemistry of Nucleic Acid Components. 16th Symposium, ISBN 978-80-86241-50-0

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0234285

Permalink: http://www.nusl.cz/ntk/nusl-174429


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