Probing the helical integrity of multivicinal all-syn-fluoro alkanes.
Org Biomol Chem
; 18(5): 878-887, 2020 02 07.
Article
em En
| MEDLINE
| ID: mdl-31942902
ABSTRACT
This study extends our interest in the synthesis and conformational behaviour of all-syn multivicinal fluoro alkane motifs. Specifically an all-syn 1,2,3,6,7,8-hexafluorooctane chain was assembled with a run of three fluorines, of the same stereochemical sense (syn) to the direction of the chain, on each side of an ethylene (-CH2CH2-) spacer to explore if the helical sense of the chain crosses the ethylene bridge. The solid state (X-ray) structure indicated a continuous helix however in solution (NMR) and by DFT computation, although the individual all-syn 1,2,3-trifluoro motifs maintain good helical integrity, the molecule is much more dynamic across the ethylene bridge. It was notable however that a low energy, non-helical conformer has a high molecular dipole (µ = 7.15 D) indicating a role for this skipped motif in soft materials such as liquid crystals or polar polymers.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Org Biomol Chem
Assunto da revista:
BIOQUIMICA
/
QUIMICA
Ano de publicação:
2020
Tipo de documento:
Article