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Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
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SYSNO ASEP 0428941 Document Type C - Proceedings Paper (int. conf.) R&D Document Type The record was not marked in the RIV Title Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines Author(s) Procházková, Eliška (UOCHB-X) RID, ORCID
Čechová, Lucie (UOCHB-X) RID, ORCID
Žurek, Jiří (UOCHB-X)
Janeba, Zlatko (UOCHB-X) RID, ORCID
Dračínský, Martin (UOCHB-X) RID, ORCIDNumber of authors 5 Source Title Chemistry of Nucleic Acid Components. 16th Symposium. - Praha : Institute of Organic Chemistry and Biochemistry AS CR, v. v. i, 2014 / Hocek M. - ISBN 978-80-86241-50-0 Pages s. 251-254 Number of pages 4 s. Publication form Print - P Action Symposium on Chemistry of Nucleic Acid Components /16./ Event date 08.06.2014-13.06.2014 VEvent location Český Krumlov Country CZ - Czech Republic Event type EUR Language eng - English Country CZ - Czech Republic Keywords intramolecular hydrogen bonds ; polysubstituted 5-nitrosopyrimidines ; NMR spectroscopy Subject RIV CC - Organic Chemistry R&D Projects GA13-24880S GA ČR - Czech Science Foundation (CSF) Institutional support UOCHB-X - RVO:61388963 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2015
Number of the records: 1