Conformation and Absolute Configuration of 2-Naphthylalkylsulfoxides by Combined Use of Dynamic NMR, ECD Spectroscopy, DFT Computations and X-Ray Diffraction

Casarini, D.; Lunazzi, Lodovico; Mancinelli, Michele; Mazzanti, Andrea; Scafato, P.

doi:10.1002/chir.20587

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The E/Z conformer ratios of five 2-naphtylalkylsulfoxides were determined by means of dynamic NMR spectroscopy at very low temperatures and this information was used to predict, by means of DFT calculations, the ECD spectra of the R and S enantiomers. The latter were separated by enantioselective HPLC technique and the comparison of theoretical and experimental ECD spectra allowed the absolute configurations to be determined. In the case of 2-naphtyltert-butylsulfoxide (1), the assignment was independently confirmed by anomalous dispersion using single crystal X-ray crystallography .

Titolo:	Conformation and Absolute Configuration of 2-Naphthylalkylsulfoxides by Combined Use of Dynamic NMR, ECD Spectroscopy, DFT Computations and X-Ray Diffraction
Autore/i:	D. Casarini; LUNAZZI, LODOVICO; MANCINELLI, MICHELE; MAZZANTI, ANDREA; P. Scafato
Autore/i Unibo:	D. Casarini LUNAZZI, LODOVICO MANCINELLI, MICHELE MAZZANTI, ANDREA P. Scafato mostra contributor esterni nascondi contributor esterni
Anno:	2009
Rivista:	CHIRALITY
Digital Object Identifier (DOI):	10.1002/chir.20587
Abstract:	The E/Z conformer ratios of five 2-naphtylalkylsulfoxides were determined by means of dynamic NMR spectroscopy at very low temperatures and this information was used to predict, by means of DFT calculations, the ECD spectra of the R and S enantiomers. The latter were separated by enantioselective HPLC technique and the comparison of theoretical and experimental ECD spectra allowed the absolute configurations to be determined. In the case of 2-naphtyltert-butylsulfoxide (1), the assignment was independently confirmed by anomalous dispersion using single crystal X-ray crystallography .
Data prodotto definitivo in UGOV:	2010-01-31 18:04:30
Appare nelle tipologie:	1.01 Articolo in rivista

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http://hdl.handle.net/11585/82943

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