Naslov
Experimental and quantum chemical study of ferrocenyl-substituted nucleobases

Autori
Blasina, Valentino ; Pezerović, Alma ; Lapić, Jasmina ; Šakić, Davor ; Sanković, Krešimir ; Djaković, Senka ; Vrček, Valerije

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

Izvornik
15. međunarodni znanstveno-stručni skup Ružičkini dani "Danas znanost - sutra industrija" : zbornik radova = 15th International Conference Ružička days "Today science - tomorrow industry" : proceedings / Šubarić, Drago - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2014

Skup
Međunarodni znanstveno-stručni skup Ružičkini dani "Danas znanost - sutra industrija" (15 ; 2014)

Mjesto i datum
Vukovar, Hrvatska, 11.09.2014. - 12.09.2014

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
ferrocene; nucleobase; synthesis; computational chemistry

Sažetak
Nucleobases substituted by ferrocenyl moiety present interesting organometallic conjugates due to their structures which incorporate both biologically and electrochemically active components. Synthetic procedures for preparation of N1- and N3-ferrocenyl substituted pyrimidine bases (thymine, cytosine) and N9-ferrocenyl substituted purine base (adenine) have been developed. The position of substitution in products has been confirmed by spectroscopy methods (NOESY-NMR, IR). Quantum chemical calculations (DFT level of theory) have been employed to rationalize the preferential reaction of ferrocenecarbonyl chloride with N1-nitrogen atom in pyrimidine nucleobases. The calculated energy of activation for the reaction at N3-position is ca. 30 kJ/mol higher than the barrier for the corresponding reaction at N1-position. In addition, N1-ferrocenyl substituted nucleobases have been calculated more stable than their N3-substituted counterparts. Substitution of pyrimidine and purine bases with the ferrocenyl moiety perturb some important intrinsic properties of the bases, such as keto-enol tautomerism and hydrogen bonding. It is expected that ferrocenyl substituted nucleobases can participate in a novel type of base pairing.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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