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

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Abstract

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 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.

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Acknowledgments

The financial support from the Croatian Ministry of Science, Education and Sports (Programs 098-1191344-2943 and 053-0982914-2965) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, 10000, Zagreb, Croatia

    Ivana Stolić & Miroslav Bajić

  2. Rudjer Bošković Institute, Bijenička 54, 10000, Zagreb, Croatia

    Krešimir Molčanov, Goran Kovačević & Biserka Kojić-Prodić

Authors
  1. Ivana Stolić
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  2. Krešimir Molčanov
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  3. Goran Kovačević
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  4. Biserka Kojić-Prodić
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  5. Miroslav Bajić
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Corresponding author

Correspondence to Miroslav Bajić.

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Stolić, I., Molčanov, K., Kovačević, G. et al. Axial chirality of N,N′-disubstituted 3,4-ethylenedioxythiophene-2,5-dicarboxamides. Struct Chem 23, 425–432 (2012). https://doi.org/10.1007/s11224-011-9885-x

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