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In 2015, chemists synthesized an unusual cyclohexane: all six fluorine atoms point to the same face of the ring, yet the molecule retains a chair shape. The structure has a reported molecular dipole of 6.2 D and unusually close fluorine–fluorine contacts. The researchers proposed that repulsive tension between those fluorines helps stabilize the chair, but the distances are structural measurements—not a direct measurement of a force.
What “single-face” means in this molecule
The compound is all-cis 1,2,3,4,5,6-hexafluorocyclohexane. “All-cis” means that the six C–F bonds point to the same side of the cyclohexane ring. It does not mean the fluorines all occupy identical positions in space: in the molecule’s chair conformation, three fluorines are axial and aligned on one face, while the other three are equatorial.
That arrangement is striking because the six electronegative fluorines create a strongly polarized face, while the carbon ring keeps the familiar chair geometry rather than adopting a different shape to separate the substituents.
What the structure and measurements show
A large molecular dipole
Keddie and coauthors reported a molecular dipole of 6.2 D, unusually large for an aliphatic compound. The value is consistent with the molecule’s one-sided distribution of fluorine atoms; it is a property of the whole molecule, not a measurement of the charge on an individual fluorine. In the solid state, the reported molecular packing orientation was also consistent with electrostatic ordering.
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Closely spaced fluorines
X-ray analysis found approximate intramolecular distances of 2.77 Å between axial fluorines and 2.73 Å between neighboring axial and equatorial fluorines. The authors interpreted these close contacts as evidence of tension that helps stabilize the observed chair. The distances themselves are structural observations; they do not independently quantify a repulsive force or prove that tension is the sole reason the chair persists.
How chemists made the all-cis compound
The researchers reported a 12-step synthesis starting from myo-inositol. They first converted it into a suitably functionalized cyclohexane precursor with oxygen substituents on one face, then replaced those substituents with fluorine through sequential deoxyfluorination reactions. Each substitution inverted the configuration at its carbon, producing the all-cis fluorinated target.
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Chemistry World’s 2015 account reported an approximate overall yield of 10%. That figure is from a secondary report and should not be treated as a yield verified here from the paper’s full experimental data. The primary article is Keddie et al., Nature Chemistry, volume 7, pages 483–488 (2015), published online on 13 April and included in the June 2015 issue. Read the paper via its DOI; an institutional manuscript and record are available from the University of St Andrews repository. The bibliographic record and abstract are also indexed by PubMed. Chemistry World’s contemporary report is available here.
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The study demonstrates a synthesis and reports a distinctive molecular structure and dipole. It does not establish that the compound is commercially available, adopted in industry, or already useful in a particular product. The authors’ suggestion that related structures could serve as motifs in functional molecules or supramolecular chemistry is a prospective research possibility, not a demonstrated application.
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