Computational and DNMR Investigation of the Isomerism and Stereodynamics of the 2,2′-Binaphthalene-1,1′-diol Scaffold

The relative stabilities of three conformational isomers of 2,2′-binaphthalene-1,1′-diol diisobutyrate and the energy barriers to rotation about the pivotal aryl–aryl bond and the two aryl–oxygen bonds were investigated by variable-temperature NMR spectroscopy in conjunction with DFT computations. T...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-04, Vol.79 (8), p.3725-3730
Main Authors: Mazzanti, Andrea, Chiarucci, Michel, Bentley, Keith W, Wolf, Christian
Format: Article
Language:English
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Summary:The relative stabilities of three conformational isomers of 2,2′-binaphthalene-1,1′-diol diisobutyrate and the energy barriers to rotation about the pivotal aryl–aryl bond and the two aryl–oxygen bonds were investigated by variable-temperature NMR spectroscopy in conjunction with DFT computations. The experimental and calculated data were found to be in very good agreement and provide new insights into the dynamic stereochemistry of BINOL-derived tropos ligands.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5005229