Generation and dissociation pathways of singly and doubly protonated bisguanidines in the gas phase (CROSBI ID 144877)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Tintaru, Aura ; Roithová, Jana ; Schröder, Detlef ; Charles, Laurence ; Jušinski, Iva ; Glasovac, Zoran ; Eckert-Maksić, Mirjana
engleski
Generation and dissociation pathways of singly and doubly protonated bisguanidines in the gas phase
Para-bisguanidinyl benzene 1 and its N-permethylated derivative 2 are both sufficiently strong bases to afford not only the monocations [1+H]+ and [2+H]+, but also the doubly protonated ions, [1+2H]2+ and [2+2H]2+, in the gas phase. The title ions generated via electrospray ionization are probed by collision-induced dissociation experiments which inter alia reveal that the dicationic species [1+2H]2+ and [2+2H]2+ can even undergo fragmentation reactions with maintenance of the two-fold charge. Complementary results from density functional theory predict PAs above 1000 kJ mol-1 for the neutral compounds, i.e. PA(1) = 1025 kJ mol-1 and PA(2) = 1067 kJ mol-1. Due to the stabilization of the positive charge in the guanidium ions and the para-phenylene spacer separating the basic sites, even the monocations bear sizable proton affinities, i.e. PA([1+H]+) = 740 kJ mol-1 and PA([2+H]+) = 816 kJ mol-1.
ensity functional theory; dications; guanidinium ions; mass spectrometry; proton affinities
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Podaci o izdanju
112 (47)
2008.
12097-12103
objavljeno
1089-5639
10.1021/jp805897f