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  Stereochemical analysis of (+)-limonene using theoretical and experimental NMR and chiroptical data.

Reinscheid, F., & Reinscheid, U. M. (2016). Stereochemical analysis of (+)-limonene using theoretical and experimental NMR and chiroptical data. Journal of Molecular Structure, 1106, 141-153. doi:10.1016/j.molstruc.2015.10.061.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0029-5AA7-3 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002E-0E84-B
Genre: Journal Article

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 Creators:
Reinscheid, F.1, Author              
Reinscheid, U. M.1, Author              
Affiliations:
1Department of NMR Based Structural Biology, MPI for Biophysical Chemistry, Max Planck Society, ou_578567              

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Free keywords: Limonene; ORD; ECD; VCD; NMR; Conformation
 Abstract: Using limonene as test molecule, the success and the limitations of three chiroptical methods (optical rotatory dispersion (ORD), electronic and vibrational circular dichroism, ECD and VCD) could be demonstrated. At quite low levels of theory (mpw1pw91/cc-pvdz, IEFPCM (integral equation formalism polarizable continuum model)) the experimental ORD values differ by less than 10 units from the calculated values. The modelling in the condensed phase still represents a challenge so that experimental NMR data were used to test for aggregation and solvent solute interactions. After establishing a reasonable structural model, only the ECD spectra prediction showed a decisive dependence on the basis set: only augmented (in the case of Dunning's basis sets) or diffuse (in the case of Pople's basis sets) basis sets predicted the position and shape of the ECD bands correctly. Based on these result we propose a procedure to assign the absolute configuration (AC) of an unknown compound using the comparison between experimental and calculated chiroptical data.

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Language(s): eng - English
 Dates: 2015-10-242016-02-15
 Publication Status: Published in print
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 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1016/j.molstruc.2015.10.061
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Title: Journal of Molecular Structure
Source Genre: Journal
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Pages: - Volume / Issue: 1106 Sequence Number: - Start / End Page: 141 - 153 Identifier: -