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Mass spectral fragmentation of adamantane-substituted guanylhydrazones


Šekutor, Marina; Glasovac, Zoran; Mlinarić-Majerski, Kata
Mass spectral fragmentation of adamantane-substituted guanylhydrazones // European-Winter School on Physical Organic Chemistry / e-WISPOC-2012
Bressanone, Italija, 2012. (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Mass spectral fragmentation of adamantane-substituted guanylhydrazones

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

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
European-Winter School on Physical Organic Chemistry / e-WISPOC-2012 / - Bressanone, Italija, 2012

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

Mjesto i datum
Bressanone, Italija, 29.01-03.02.2012

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Adamantane; Mass spectroscopy; Guanylhydrazone; Cooperativity effects

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )
098-0982933-2920 - Organski i bioorganski procesi u osnovnom i elektronski pobuđenim stanjima (Mirjana Maksić, )

Ustanove
Institut "Ruđer Bošković", Zagreb