A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines

Popis výsledku anglicky

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

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

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Svazek periodika

78

Číslo periodika v rámci svazku

20

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

13

Strana od-do

10121-10133

Kód UT WoS článku

000326122200009

EID výsledku v databázi Scopus

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