Axial chirality of N,N%26apos;-disubstituted 3,4-ethylenedioxythiophene-2,5-dicarboxamides

作者：Stolic Ivana; Molcanov Kresimir; Kovacevic Goran; Kojic Prodic Biserka; Bajic Miroslav^*

来源：Structural Chemistry, 2012, 23(2): 425-432.

DOI：10.1007/s11224-011-9885-x

• 3,4-Ethylenedioxythiophene
• Crystal structure
• Axial chirality
• DFT

A series of N,N%26apos;-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 C (2). Amide bond isomerisation 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 favourable.

• 出版日期2012-4