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Issue 21, 2012
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Structural analysis of two foldamer-type oligoamides – the effect of hydrogen bonding on solvate formation, crystal structures and molecular conformation

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Abstract

The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed. One polymorphic form and seven solvates were found for N1,N3-bis(2-benzamidophenyl)benzene-1,3-dicarboxamide (the benzene variant), and two polymorphic forms and six solvates for N2,N6-bis(2-benzamidophenyl)pyridine-2,6-dicarboxamide (the pyridine variant). Three crystal structures of the benzene variant and seven structures of the pyridine variant were solved using single crystal X-ray diffraction. The crystal structures showed that the different modes of intramolecular hydrogen bonding strongly affect the conformation and folding of the molecules, which is most evidently seen with the strongly folded helical structure of the pyridine variant. NOESY experiments suggest that the intramolecular hydrogen bonding is stable enough to retain a folded or partially folded conformation even in solution.

Graphical abstract: Structural analysis of two foldamer-type oligoamides – the effect of hydrogen bonding on solvate formation, crystal structures and molecular conformation

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Publication details

The article was received on 19 Jun 2012, accepted on 17 Aug 2012 and first published on 21 Aug 2012


Article type: Paper
DOI: 10.1039/C2CE25981H
Citation: CrystEngComm, 2012,14, 7398-7407
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    Structural analysis of two foldamer-type oligoamides – the effect of hydrogen bonding on solvate formation, crystal structures and molecular conformation

    A. Suhonen, E. Nauha, K. Salorinne, K. Helttunen and M. Nissinen, CrystEngComm, 2012, 14, 7398
    DOI: 10.1039/C2CE25981H

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