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In the meso compound, there are two homotopic protons/carbons per site. For the pair of enantiomers, each such pair is formally diastereotopic: DFT calculations predict that each stereoisomer exists as a mixture of rotamers about the inter- ring bond (electronic energies, B3LYP-D3(BJ)/cc-pVTZ/PCM(DMSO) // B3LYP/6- 31G*/PCM(DMSO)). In the meso form, rotation is a chemical exchange process between isochronous sites. In the DL form, to a very good approximation (see predictions below), rotation converts the diastereotopic partners into one another. 29PDF Image | Extending organic flow batteries via redox state management
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