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

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 seconda...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-07, Vol.21 (29), p.5939-5943
Main Authors: abka, Matej, Clayden, Jonathan
Format: Article
Language:English
Subjects:
Acidification
Bonding strength
Chemistry
Dipoles
Fluorine
Hydrogen
Hydrogen bonding
Hydrogen bonds
Protein structure
Secondary structure
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Summary: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. The conformation of bisdifluoroacetamides is governed by dipole effects, rather than CH O hydrogen bonds.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00811h