The syn and anti diastereoisomers of some 1,3,5-triarylisocyanurate derivatives were isolated and their configurationassigned by NOE experiments and by X-ray diffraction. The kinetics of the syn/anti interconversion were determined, and the experimental activation energies matched satisfactorily the values predicted by DFT computations. Low-temperature NMR spectra were employed to determine the rotation barrier of N-bonded unhindered aryl substituents: these barriers, too, are satisfactorily reproduced by DFT computations. In the case of racemic diastereoisomers, the two expected enantiomers (atropisomers) were isolated by enantioselective HPLC and the absolute configuration established by DFT simulation of the electronic and vibrational circular dichroism spectra

Atropisomers of Hindered Triarylisocyanurates: Structure, Conformation, Stereodynamics, and Absolute Configuration.

LUNAZZI, LODOVICO;MANCINELLI, MICHELE;MAZZANTI, ANDREA
2012

Abstract

The syn and anti diastereoisomers of some 1,3,5-triarylisocyanurate derivatives were isolated and their configurationassigned by NOE experiments and by X-ray diffraction. The kinetics of the syn/anti interconversion were determined, and the experimental activation energies matched satisfactorily the values predicted by DFT computations. Low-temperature NMR spectra were employed to determine the rotation barrier of N-bonded unhindered aryl substituents: these barriers, too, are satisfactorily reproduced by DFT computations. In the case of racemic diastereoisomers, the two expected enantiomers (atropisomers) were isolated by enantioselective HPLC and the absolute configuration established by DFT simulation of the electronic and vibrational circular dichroism spectra
JOURNAL OF ORGANIC CHEMISTRY
L. Lunazzi; M.Mancinelli; A.Mazzanti
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/117315
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