About: A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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 broad range 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. 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 broad range 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. (en)
Title	A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines (en)
skos:prefLabel	A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines A Switchable Intramolecular Hydrogen Bond in Polysubstituted 5-Nitrosopyrimidines (en)
skos:notation	RIV/61388963:_____/13:00399137!RIV14-MV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GA13-24880S), P(VG20102015046)
http://linked.open...iv/cisloPeriodika	20
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Janeba, Zlatko Dračínský, Martin Čechová, Lucie Procházková, Eliška
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	59129
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/13:00399137
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	NMR spectroscopy; pyrimidines; DFT calculations (en)
http://linked.open.../riv/klicoveSlovo	NMR spectroscopy DFT calculations pyrimidines
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[D2428AE73484]
http://linked.open...i/riv/nazevZdroje	Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Struktura a vlastnosti modifikovaných složek nukleových kyselin Targeted drug design for bioterrorism prevention. Development of effective inhibitors of the adenylate cyclase toxin of Bordetella pertusis and Bacillus anthracis.
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	78
http://linked.open...iv/tvurceVysledku	Dračínský, Martin Janeba, Zlatko Čechová, Lucie Procházková, Eliška
http://linked.open...ain/vavai/riv/wos	000326122200009
issn	0022-3263
number of pages	13 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jo401441z

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