Document Detail

Conformational preference of a chiral terpene: vibrational circular dichroism (VCD), infrared and Raman study of S-(-)-limonene oxide.
MedLine Citation:
PMID:  19325979     Owner:  NLM     Status:  MEDLINE    
S-(-)-Limonene oxide (4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane) is a secondary metabolite and an atmospheric pollutant product of oxidation of other terpenes, such as limonene and alpha-pinene, among others. For the first time, a theoretical study of the molecular structure and a theoretical and experimental analysis of the infrared and Raman spectra of this chemical species are presented. Theoretical calculations reveal the existence of two conformers depending on the position of the isopropenyl group (axial and equatorial) and twelve rotamers (six equatorials and six axials), with the six equatorial ones as the most stable (around 97%) on the basis of Boltzmann's distribution law. In the current work, from a reliable assignment of the IR and Raman spectra and with the help from the study of the VCD spectrum of the title compound, five rotamers have been detected experimentally in the liquid phase. The present work reveals that IR, Raman and VCD are helpful complementary techniques to characterize flexible systems, as terpenes, which present several conformers.
Juan Ramón Avilés Moreno; Francisco Partal Ureña; Juan Jesús López González
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-02-12
Journal Detail:
Title:  Physical chemistry chemical physics : PCCP     Volume:  11     ISSN:  1463-9076     ISO Abbreviation:  Phys Chem Chem Phys     Publication Date:  2009 Apr 
Date Detail:
Created Date:  2009-03-27     Completed Date:  2009-06-10     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100888160     Medline TA:  Phys Chem Chem Phys     Country:  England    
Other Details:
Languages:  eng     Pagination:  2459-67     Citation Subset:  IM    
University of Jaén, Department of Physical and Analytical Chemistry, Campus Las Lagunillas, Jaén, E-23071, Spain.
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MeSH Terms
Circular Dichroism
Molecular Conformation*
Monoterpenes / chemistry*
Quantum Theory
Spectrophotometry, Infrared
Spectrum Analysis, Raman
Reg. No./Substance:
0/Monoterpenes; 1195-92-2/limonene-1,2-epoxide

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