Abstract
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.
Original language | English |
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Article number | e202200177 |
Number of pages | 5 |
Journal | Helvetica Chimica Acta |
Volume | 106 |
Issue number | 2 |
Early online date | 31 Jan 2023 |
DOIs | |
Publication status | Published - 20 Feb 2023 |
Keywords
- Synthesis
- Fluorine
- Deuterium
- Cyclopentane
- Janus face
- Isotopologues