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Issue 9, 2011
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Conformational aspects in the studies of organic compounds by electronic circular dichroism

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Abstract

The electronic circular dichroism (ECD) spectra of flexible molecules include the contributions of all conformers populated at the working temperature. ECD spectra of chiral substrates depend on their stereochemistry in terms of both absolute configuration, as reflected in the sign of the spectrum, and molecular conformation, which dictates the overall spectral shape (possibly including the sign) in a very sensitive manner. The unique high sensitivity of ECD towards conformation, as well as of other chiroptical spectroscopies, renders these techniques a useful alternative or complement to standard spectroscopic tools for conformational investigations, such as NMR. This tutorial review provides first a brief discussion of the main principles of ECD spectroscopy and related methods for interpretation of spectra, with special reference to conformational aspects. The review focuses on the common problems encountered in the application of ECD for assignments of absolute configuration of flexible molecules. These problems can be handled either by taking into account the whole conformational ensemble or by considering rigid derivatives prepared ad hoc. Finally, the review presents the relatively less common but very interesting application of ECD spectroscopy for conformational analyses of organic compounds.

Graphical abstract: Conformational aspects in the studies of organic compounds by electronic circular dichroism

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Article information


Submitted
08 Feb 2011
First published
15 Jun 2011

Chem. Soc. Rev., 2011,40, 4603-4625
Article type
Tutorial Review

Conformational aspects in the studies of organic compounds by electronic circular dichroism

G. Pescitelli, L. Di Bari and N. Berova, Chem. Soc. Rev., 2011, 40, 4603
DOI: 10.1039/C1CS15036G

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