Naslov
Dinuclear ferrocene derivatives as a model system to study the effect of variable spacer length on hydrogen bond patterns

Autori
Kodrin, Ivan ; Kovač, Veronika ; Barišić, Lidija ; Molčanov, Krešimir

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

Izvornik
25. hrvatski skup kemičara i kemijskih inženjera / Šantić, Ana ; Đaković, Marijana - Zagreb : Hrvatsko kemijsko društvo, 2017, 160-160

ISBN
978-953-55232-7-7

Skup
25. hrvatski skup kemičara i kemijskih inženjera

Mjesto i datum
Poreč, Hrvatska, 19.04.2017. - 22.04.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
ferocenski peptidomimetici, vodikova veza, konformacijska analiza, DFT
(ferrocene peptidomimetic, hydrogen bond, conformational analysis, DFT)

Sažetak
Ferrocene-containing derivatives with only one ferrocene unit and two small peptide chains attached to each cyclopentadienyl ring show a great potential for formation of intra- or interchain hydrogen bonds because of a restricted rotation of these rings. An engagement of two ferrocene units imposes additional conformational flexibility in comparison to the mononuclear ferrocenes. The first oxalamide-bridged dinuclear ferrocene compound with acetyl groups did not show any preference for intramolecular hydrogen bonding. In addition, these compounds did not exhibit any self-assembly and gelation properties, although some of the mononuclear ferrocene- containing and bis(amino acid)-oxalamide derivatives have already been proven as gelators. If we want to predict the self-assembly and gelation properties of oxalamide-bridged dinuclear ferrocene peptides, firstly we need to fully understand the supramolecular structure and its relationship with molecular structure of single molecules. In order to make a clear distinction between affinities of potential hydrogen bond donor and acceptor sites toward inter- or intramolecular hydrogen bonding we performed a detailed conformational study by means of computational chemistry methods (DFT, QTAIM). The results were compared with those obtained by previously conducted experiments. In the course of this research, an improved procedure for syntheses of higher analogues of oxalamide-bridged dinuclear ferrocene compounds is described. In comparison with the first oxalamide-bridged compound these analogues differ in spacer length and sizes of the oppositely attached peptide chains. The total number of potential hydrogen bond donors and acceptor sites increases in both compounds, thus resulting in the formation of multiple intramolecular hydrogen bonds. Nevertheless, some of these sites remain free and able to trigger unidirectional self-assembly and gelation behavior due to intermolecular hydrogen bonding.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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