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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

Fenchone, camphor, 2-methylenefenchone and 2-methylenecamphor: a vibrational circular dichroism study.

We report and discuss the infrared (IR) vibrational circular dichroism (VCD) spectra of the enantiomeric pairs of the olefin derivatives of fenchone (1,3,3-trimethyl-2-methylenebicyclo[2.2.1]heptane) and camphor (1,7,7-trimethyl-2-methylenebicyclo[2.2.1]heptane), respectively, together with those of the parent molecules. The VCD spectra were taken in three spectral regions: the mid-IR region, encompassing the fundamental deformation modes, the region of CH-stretching fundamental modes and the NIR-region between 1100 and 1300 nm, which corresponds to the second CH-stretching overtone. The VCD and absorption spectra in the first two regions are analyzed by use of current density functional theory (DFT) calculations. The NIR region is analyzed by a protocol that consists of the use of DFT-based calculations and in assuming local mode behavior: the local mode approach is found appropriate for interpreting the absorption spectra and, for the moment, acceptable for calculating NIR-VCD spectra. The analysis of the first region allows us to track the contribution of the C=O group in the vibrational optical activity of C-C stretching modes; notable differences are indeed found in olefins and ketones. On the contrary, in the other two regions the VCD spectra of olefins and ketones are more similar: in the normal mode region of CH stretching fundamentals the spectra are determined by the mutual orientation of the CH bonds; in the second overtone local mode region olefins and ketones signals show some differences.[1]

References

  1. Fenchone, camphor, 2-methylenefenchone and 2-methylenecamphor: a vibrational circular dichroism study. Longhi, G., Abbate, S., Gangemi, R., Giorgio, E., Rosini, C. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
 
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