Title
Conformational landscape in chiral terpenes from vibrational spectroscopy and quantum chemical calculations: S-(+)-carvone
Author
Juan Ramón Avilés Moreno, Francisco Partal Ureña, Juan Jesús López González
Year
2009
Journal
Vibrational Spectroscopy
Abstract
S-(+)-carvone (5-isopropenyl-2-methylcyclohex-2-en-1-one) is the primary component in the oil of caraway. Different experimental and theoretical works reveal that there are two possible conformers in which the isopropenyl group can be in equatorial or axial position. For each one, three rotamers were found theoretically, with the equatorial rotamers around 95% of the whole statistical population. In the current work, from a complete assignment of the IR and Raman spectra and the results obtained from the study of the VCD spectrum of the title compound, the three most stable rotamers have been detected experimentally in the liquid phase for the first time. The present work reveals that IR, Raman and VCD are helpful complementary techniques to characterize flexible systems, as terpenes, which present several conformers.
Instrument
FVS-4000
Keywords
Vibrational circular dichorism, Quantum chemical calculations, SQMFF methodologyChiral terpenesS-(+)-carvone