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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F12%3A00379222%21RIV13-AV0-61388963
rdf:type
n5:Vysledek skos:Concept
dcterms: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.
dcterms: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
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
skos:notation
RIV/61388963:_____/12:00379222!RIV13-AV0-61388963
n5:predkladatel
n6:ico%3A61388963
n3:aktivita
n17:I
n3:aktivity
I
n3:cisloPeriodika
20
n3:dodaniDat
n4:2013
n3:domaciTvurceVysledku
Schröder, Detlef Polyakova, Svetlana Kunetskiy, Roman Alexejevič
n3:druhVysledku
n14:J
n3:duvernostUdaju
n13:S
n3:entitaPredkladatele
n16:predkladatel
n3:idSjednocenehoVysledku
170804
n3:idVysledku
RIV/61388963:_____/12:00379222
n3:jazykVysledku
n9:eng
n3:klicovaSlova
carbenes; cations; collision-induced dissociation; density functional calculations; electrospray ionization; lipophilic cations; mass spectrometry; phase-transfer catalysis
n3:klicoveSlovo
n8:electrospray%20ionization n8:carbenes n8:mass%20spectrometry n8:cations n8:phase-transfer%20catalysis n8:density%20functional%20calculations n8:lipophilic%20cations n8:collision-induced%20dissociation
n3:kodStatuVydavatele
DE - Spolková republika Německo
n3:kontrolniKodProRIV
[938FB0B5DFA1]
n3:nazevZdroje
European Journal of Organic Chemistry
n3:obor
n11:CC
n3:pocetDomacichTvurcuVysledku
3
n3:pocetTvurcuVysledku
3
n3:rokUplatneniVysledku
n4:2012
n3:tvurceVysledku
Kunetskiy, Roman Alexejevič Schröder, Detlef Polyakova, Svetlana
n3:wos
000305942800016
s:issn
1434-193X
s:numberOfPages
11
n15:doi
10.1002/ejoc.201200386