About: Stabilities of Immonium Ions Derived from N-Heterocyclic Carbenes Probed by Collision-Induced Dissociation Mass Spectrometry

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	We report efficient methods for the synthesis of both symmetrically and non-symmetrically substituted bis(imidazol-2-yliden)ammonium ions and a new family of bis(imidazol-2-ylidene)formamidines. The fragmentation pathways of these cations were studied in detail by electrospray ionization combined with tandem mass spectrometry. Interestingly, in these cations direct CN bond cleavage leading to loss of alkyl radicals can compete with rearrangement reactions leading to closed-shell fragments. The experimental results for the major fragmentation channels are compared with those derived from DFT calculations. Inter alia, a novel rearrangement of the cationic species involving specific alkyl migrations between the two imidazole subunits has been found. We report efficient methods for the synthesis of both symmetrically and non-symmetrically substituted bis(imidazol-2-yliden)ammonium ions and a new family of bis(imidazol-2-ylidene)formamidines. The fragmentation pathways of these cations were studied in detail by electrospray ionization combined with tandem mass spectrometry. Interestingly, in these cations direct CN bond cleavage leading to loss of alkyl radicals can compete with rearrangement reactions leading to closed-shell fragments. The experimental results for the major fragmentation channels are compared with those derived from DFT calculations. Inter alia, a novel rearrangement of the cationic species involving specific alkyl migrations between the two imidazole subunits has been found. (en)
Title	Stabilities of Immonium Ions Derived from N-Heterocyclic Carbenes Probed by Collision-Induced Dissociation Mass Spectrometry Stabilities of Immonium Ions Derived from N-Heterocyclic Carbenes Probed by Collision-Induced Dissociation Mass Spectrometry (en)
skos:prefLabel	Stabilities of Immonium Ions Derived from N-Heterocyclic Carbenes Probed by Collision-Induced Dissociation Mass Spectrometry Stabilities of Immonium Ions Derived from N-Heterocyclic Carbenes Probed by Collision-Induced Dissociation Mass Spectrometry (en)
skos:notation	RIV/61388963:_____/12:00379222!RIV13-AV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	I
http://linked.open...avai/riv/aktivity	I
http://linked.open...iv/cisloPeriodika	20
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Schröder, Detlef Kunetskiy, Roman Alexejevič Polyakova, Svetlana
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	170804
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00379222
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	carbenes; cations; collision-induced dissociation; density functional calculations; electrospray ionization; lipophilic cations; mass spectrometry; phase-transfer catalysis (en)
http://linked.open.../riv/klicoveSlovo	cations collision-induced dissociation electrospray ionization mass spectrometry carbenes lipophilic cations phase-transfer catalysis density functional calculations
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[938FB0B5DFA1]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...UplatneniVysledku	2012
http://linked.open...iv/tvurceVysledku	Schröder, Detlef Kunetskiy, Roman Alexejevič Polyakova, Svetlana
http://linked.open...ain/vavai/riv/wos	000305942800016
issn	1434-193X
number of pages	11 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201200386
is http://linked.open...avai/riv/vysledek of	Stabilities of Immonium Ions Derived from N-Heterocyclic Carbenes Probed by Collision-Induced Dissociation Mass Spectrometry

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