Issue 24, 2008
From the journal:

Physical Chemistry Chemical Physics

Solvent effects on IR and VCDspectra of natural products: an experimental and theoretical VCD study of pulegone†

Elke Debie,a   Patrick Bultinck,*a   Wouter Herreboutb  and  Benjamin van der Vekenb  

* Corresponding authors

a Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, Ghent, Belgium
E-mail: Patrick.Bultinck@UGent.be
Fax: +32 92644983
Tel: +32 92644423

b Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, Antwerp, Belgium

Abstract

The VCD spectra of pulegone, dissolved in CDCl3, CD2Cl2 and CS2 have been recorded in the frequency range from 1000 to 3000 cm−1. The assignment of the absolute configuration was performed by comparing the experimental data with theoretical spectra computed at the B3LYP/6-311+G(d,p) level. Analysis of the agreement in several spectral regions revealed significant shortcomings when comparing with vacuum calculations. It is shown that the agreement improves when the solvent effects are taken into account by a continuum model. For the measurements in CDCl3 and CD2Cl2 further improvement was found when considering explicitly 1 : 1 complexes between a pulegone and a CDCl3 or CD2Cl2solvent molecule in vacuo, while the best agreement was obtained when embedding these in a continuum model. The presence of the chiral solute was found to induce a VCD active C–D stretch band which could be modeled also at ab initio level.

Graphical abstract: Solvent effects on IR and VCD spectra of natural products: an experimental and theoretical VCD study of pulegone

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Article information

DOI
https://doi.org/10.1039/B801313F
Article type
Paper
Submitted
23 Jan 2008
Accepted
27 Mar 2008
First published
07 May 2008

Phys. Chem. Chem. Phys., 2008,10, 3498-3508

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Solvent effects on IR and VCD spectra of natural products: an experimental and theoretical VCD study of pulegone

E. Debie, P. Bultinck, W. Herrebout and B. van der Veken, Phys. Chem. Chem. Phys., 2008, 10, 3498 DOI: 10.1039/B801313F

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