Does Perdeuteration Increase the Polarity of Janus Face Cycloalkanes?

Stimulated by a suggestion of the late Professor Jack D. Dunitz, that perdeuterated Janus face cycloalkanes may be more polar than their unlabelled forms, the deuterated isotopologue of all cis‐1,2,3,4,5,6‐hexafluorocyclohexane ([2H6]‐1a) and all cis‐1,2,3,4‐tetrafluorocyclopentane ([2H6]‐3a) were p...

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Bibliographic Details
Published in:Helvetica chimica acta 2023-02, Vol.106 (2), p.n/a
Main Authors: Fang, Zeguo, Yu, Cihang, Bühl, Michael, O'Hagan, David
Format: Article
Language:English
Subjects:
Cycloalkanes
Cyclopentane
Deuteration
deuterium
fluorine
isotopologues
Janus face
Polarity
Retention time
synthesis
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Summary:Stimulated by a suggestion of the late Professor Jack D. Dunitz, that perdeuterated Janus face cycloalkanes may be more polar than their unlabelled forms, the deuterated isotopologue of all cis‐1,2,3,4,5,6‐hexafluorocyclohexane ([2H6]‐1a) and all cis‐1,2,3,4‐tetrafluorocyclopentane ([2H6]‐3a) were prepared. Computation at the B3LYP−D3 level indicated that [2H6]‐1a is not more polar than its protio form 1, however perdeuterated cyclopentane [2H6]‐3a may indeed be more polar than 3, although the magnitude is predicted to be small. None‐the‐less retention time analysis on a reverse phase GC/MS column of an add‐mix of 3 and [2H6]‐3a gave some indication that the per‐deuterated isotopologue 3a was detected marginally before the unlabelled compound consistent with increased polarity associated with perdeuteration.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202200177