Naslov
Axial chirality of N, N′-disubstituted 3, 4-ethylenedioxythiophene-2, 5-dicarboxamides

Autori
Stolić, Ivana ; Molčanov, Krešimir ; Kovačević, Goran ; Kojić-Prodić, Biserka ; Bajić, Miroslav

Izvornik
Structural chemistry (1040-0400) 23 (2012), 2; 425-432

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
3; 4-ethylenedioxythiophene; crystal structure; axial chirality; DFT

Sažetak
A series of N, N'-disubstituted 3, 4-ethylenedioxythiophene-2, 5-dicarboxamides was synthesised by amide bond formation between 3, 4-ethylenedioxythiophene-2, 5-dicarbonyl chloride and corresponding primary amines, where the size and the nature of the substituent were varied. The crystal structures of prepared compounds were determined by X-ray structure analysis. Mechanism and reaction rates of interconversion between conformational isomers were obtained by DFT calculations. All studied compounds reveal axial chirality with molecular symmetry C2. Amide bond isomerization and twisting of the dioxane ring in studied compounds results in the formation of series of conformers of which the s-trans/s-trans conformer is energetically most favorable.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA