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Racemization mechanism of axially chiral sym-tetraacetylethane: axial rotation vs. intramolecular proton migration.

Created on 18 Sep 2026

Authors

Mingyue Liu, Bao Zhang, Mingliang Chen, Shuo Wang, Xiangge Zhou, Haifeng Xiang

Published in

Chemical communications (Cambridge, England). Sep 18, 2026. Epub Sep 18, 2026.

Abstract

Despite a high rotational barrier from ortho-methyl groups, sym-tetraacetylethane-a distally axially chiral molecule with intramolecular hydrogen bonds-cannot be resolved by chiral HPLC. DFT reveals an unusual racemization pathway via hydrogen-bond-assisted intramolecular proton migration (barrier 1.33-3.00 kcal mol-1) that interconverts enantiomers without axial rotation or bond breaking, supported by NMR and UV-vis spectra.

PMID:
42758087
Bibliographic data and abstract were imported from PubMed on 18 Sep 2026.

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