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Physical Chemistry Chemical Physics
Article . 2008 . Peer-reviewed
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Solvent effects on IR and VCD spectra of natural products: an experimental and theoretical VCD study of pulegone

Authors: Debie, Elke; Bultinck, Patrick; Herrebout, Wouter; van der Veken, Benjamin;

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

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 CD2Cl2 solvent 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.

Country
Belgium
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Keywords

Biological Products, Spectrophotometry, Infrared, Circular Dichroism, Stereoisomerism, Cyclohexane Monoterpenes, Deuterium, Camphor, Carbon Disulfide, Hydrocarbons, Chlorinated, Monoterpenes, Solvents, Artifacts

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Powered by OpenAIRE graph
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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
67
Top 10%
Top 10%
Top 10%
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