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Axial chirality of N, N′-disubstituted 3, 4-ethylenedioxythiophene-2, 5-dicarboxamides (CROSBI ID 174152)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Stolić, Ivana ; Molčanov, Krešimir ; Kovačević, Goran ; Kojić-Prodić, Biserka ; Bajić, Miroslav Axial chirality of N, N′-disubstituted 3, 4-ethylenedioxythiophene-2, 5-dicarboxamides // Structural chemistry, 23 (2012), 2; 425-432. doi: 10.1007/s11224-011-9885-x

Podaci o odgovornosti

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

engleski

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

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.

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

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Podaci o izdanju

23 (2)

2012.

425-432

objavljeno

1040-0400

10.1007/s11224-011-9885-x

Povezanost rada

Kemija

Poveznice
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