Does perdeuteration increase the polarity of Janus face cycloalkanes?
Date
20/02/2023Metadata
Show full item recordAbstract
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.
Citation
Fang , Z , Yu , C , Bühl , M & O'Hagan , D 2023 , ' Does perdeuteration increase the polarity of Janus face cycloalkanes? ' , Helvetica Chimica Acta , vol. 106 , no. 2 , e202200177 . https://doi.org/10.1002/hlca.202200177
Publication
Helvetica Chimica Acta
Status
Peer reviewed
ISSN
0018-019XType
Journal article
Description
Funding: Authors are grateful to the Chinese Scholarship Council for studentship (Z. F. and C. Y.) support and also the Scientific Research Project of Hubei Education Department (Q20211402) and the open project of Hubei Provincial Key Laboratory of Green Materials for Light Industry (202107B06) for financial support.Collections
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