A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00399137" target="_blank" >RIV/61388963:_____/13:00399137 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/jo401441z" target="_blank" >http://dx.doi.org/10.1021/jo401441z</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo401441z" target="_blank" >10.1021/jo401441z</a>

Result language
angličtina
Original language name
A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines
Original language description
The formation of strong intramolecular hydrogen bonds was observed in a series of 2-amino-5-nitrosopyrimidines with alkylamino and arylamino substituents at 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. The ratio of the two rotamers depends strongly on the character of the substituents at positions 4 and 6 and can be finely tuned over a broadrange of conformation ratios. The experimental results were supported by DFT calculations, which also made it possible to explain the apparent contradiction in the experimental dependence of the rotamer ratio on the Hammett constants for the arylamino substituents. The UV/vis spectra of the compounds also significantly depend on the nature of the substituents; however, the orientation of the nitroso group does not have any influence on the position of the absorption bands in the spectra
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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