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Conformational preference in difluoroacetamide oligomers: probing the potential for foldamers with C-H⋯O hydrogen bonds.

ABSTRACT: The C-H bond of a difluoroacetamide group, acidified by two adjacent fluorine atoms, could in principle provide conformational organisation for foldamers based on C-H⋯O hydrogen bonds. We find that in model oligomeric systems, this weak hydrogen bond leads only to partial organisation of the secondary structure, with the conformational preference of the difluoroacetamide groups being predominantly governed by dipole stabilisation.

SUBMITTER: Zabka M

PROVIDER: S-EPMC10369364 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Conformational preference in difluoroacetamide oligomers: probing the potential for foldamers with C-H⋯O hydrogen bonds.

Žabka Matej M Clayden Jonathan J

Organic & biomolecular chemistry 20230726 29

The C-H bond of a difluoroacetamide group, acidified by two adjacent fluorine atoms, could in principle provide conformational organisation for foldamers based on C-H⋯O hydrogen bonds. We find that in model oligomeric systems, this weak hydrogen bond leads only to partial organisation of the secondary structure, with the conformational preference of the difluoroacetamide groups being predominantly governed by dipole stabilisation. ...[more]

PMID: 37436098

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