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Neighboring Effect in Fragmentation Pathways of Cage 2 Guanylhydrazones in the Gas Phase (CROSBI ID 190904)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Šekutor, Marina ; Glasovac, Zoran ; Mlinarić-Majerski, Kata Neighboring Effect in Fragmentation Pathways of Cage 2 Guanylhydrazones in the Gas Phase // The journal of physical chemistry. A, 117 (2013), 10; 2242-2252. doi: 10.1021/jp311049f

Podaci o odgovornosti

Šekutor, Marina ; Glasovac, Zoran ; Mlinarić-Majerski, Kata

engleski

Neighboring Effect in Fragmentation Pathways of Cage 2 Guanylhydrazones in the Gas Phase

ESI-MS/MS investigation of the mono- and bisguanylhydrazone derivatives 1-5 based on adamantane and pentacycloundecane (PCU) skeleton was described. Elimination of neutral guanidine is the most abundant reaction channel in the case of 2, 4-adamantyl and PCU derivatives 4 and 5, while the elimination of CH2N2 fragment is preferred for other compounds. This was attributed to the cage opening of adamantane or PCU skeletons in the former case leading to the formation of the cyclohexyl- or cyclopropylcarbinyl carbocation stabilized by the conjugation with the guanylhydrazone subunit. The main fragmentation pathways observed experimentally were analyzed by using DFT calculations. All investigated bisguanylhydrazones formed dications and their abundances were found to be proportional to the interguanidine distance in the considered ions. Calculation of the first and the second proton affinities supported qualitative interpretation of the dication abundance. Close contact of two guanidine subunits is thus confirmed to be crucial in determining preferential fragmentation pathway and to suppress formation of the dication.

polycyclic guanylhydrazones; neighboring effect;; electrospray ionization; mass spectrometry; density functional theory

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Podaci o izdanju

117 (10)

2013.

2242-2252

objavljeno

1089-5639

10.1021/jp311049f

Povezanost rada

Kemija

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