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Germacrene D Cyclization: An Ab Initio Investigation
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
Received: 17 December 2007; Accepted: 23 January 2008 / Published: 25 January 2008
Abstract: Essential oils that contain large concentrations of germacrene D are typically accompanied by cadinane sesquiterpenoids. The acid-catalyzed cyclization of germacrene D to give cadinane and selinane sesquiterpenes has been computationally investigated using both density functional (B3LYP/6-31G*) and post Hartree-Fock (MP2/6-31G**) ab initio methods. The calculated energies are in general agreement with experimentally observed product distributions, both from acid-catalyzed cyclizations as well as distribution of the compounds in essential oils.
Keywords: germacrene D; cadinene; muurolene; amorphene; selinene; density functional theory; ab initio molecular orbital theory.
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Setzer, W.N. Germacrene D Cyclization: An Ab Initio Investigation. Int. J. Mol. Sci. 2008, 9, 89-97.
Setzer WN. Germacrene D Cyclization: An Ab Initio Investigation. International Journal of Molecular Sciences. 2008; 9(1):89-97.
Setzer, William N. 2008. "Germacrene D Cyclization: An Ab Initio Investigation." Int. J. Mol. Sci. 9, no. 1: 89-97.