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Mass spectral fragmentation of adamantane-substituted guanylhydrazones (CROSBI ID 584513)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Šekutor, Marina ; Glasovac, Zoran ; Mlinarić-Majerski, Kata Mass spectral fragmentation of adamantane-substituted guanylhydrazones // European-Winter School on Physical Organic Chemistry / e-WISPOC-2012. Brixen, 2012

Podaci o odgovornosti

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

engleski

Mass spectral fragmentation of adamantane-substituted guanylhydrazones

Adamantane is a widely used structural moiety with numerous applications, from biological chemistry to material sciences, which is a consequence of its unique structure and pronounced lipophilicity.1 Likewise, guanidinium ions are known as biologically active compounds and we hoped for an interesting synergic effects by combining these two structural motifs. The substitution places of the adamantane molecule provide a suitable system for the comparative investigation of interaction of two separated guanylhydrazone moieties by electrospray ionization (ESI) mass spectroscopy.2 This widely recognized technique has recently been successfully employed in gas-phase investigations of charge-charge interactions in dications derived from phenylenebis(guanidines).In search of cooperativity effects, we synthesized differently substituted adamantane guanylhydrazones 1‒4 and a pentacycloundecane guanylhydrazone 5. The results from the MS spectra for the monosubstituted derivatives 1 and 2 have been compared to compounds 3, 4 and 5. The underlying feature of this series is a varying spatial distance between substituents which is the largest for compound 3, somewhat smaller for 4 and for compound 5 it approximates the length of one CC bond. In addition, theoretical calculations have been performed to confirm the experimental results and to further clarify the fragmentation pathways.

Adamantane; Mass spectroscopy; Guanylhydrazone; Cooperativity effects

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Podaci o prilogu

2012.

objavljeno

Podaci o matičnoj publikaciji

European-Winter School on Physical Organic Chemistry / e-WISPOC-2012

Brixen:

Podaci o skupu

European-Winter School on Physical Organic Chemistry / e-WiSPOC-2012 / Bressanone, Italy

poster

29.01.2012-03.02.2012

Bressanone, Italija

Povezanost rada

Kemija