Conformational analysis and DFT calculations of 8α-hydroxy-germacradiene-6,12-olide derivatives

6533b824fe1ef96bd127fe57

RESEARCH PRODUCT

Conformational analysis and DFT calculations of 8α-hydroxy-germacradiene-6,12-olide derivatives

Giampaolo Barone Sergio Rosselli Dario Duca Antonella Maggio Maurizio Bruno

subject

Crystallography Chemistry Computational chemistry Organic Chemistry Physical and Theoretical Chemistry Carbon-13 NMR Spectral line

description

The Systematic Conformational Search Analysis (SCSA) code was employed to study the conformational properties of the 8α-hydroxy-germacradiene-6,12-olide isomers. This procedure was extended to the trans,cis- and trans,trans-1(10),4-isomers of 8α,15-dihydroxy-germacradiene-6,12-olides and 8α-hydroxy-15-oxo-germacradiene-6,12-olides, to investigate structural and energetic analogies between these and the 8α-hydroxy-germacradiene-6,12-olide species. The calculated 13C NMR spectra, at the hybrid DFT mPW1PW91 level, showed a sound correlation with the corresponding experimental spectra, providing a valid support to the reliability of the calculated structures and to the consistence of our conformational analysis. The results presented here allowed us to support our previous mechanistic interpretation on the oxidation of 8α,15-dihydroxy-trans,trans-1(10),4-germacradiene-6,12-olides to 8α-hydroxy-15-oxo-trans,cis-1(10),4-germacradiene-6,12-olides. Copyright © 2005 John Wiley & Sons, Ltd.

year	journal	country	edition	language
2005-11-01	Journal of Physical Organic Chemistry

https://doi.org/10.1002/poc.976

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