NBO analysis is a powerful computational tool that allows quantitative estimation of the energy of hyperconjugative effects. The structure and relative stability for a series of unsaturated decalactones (Figure 1  , exemplified for 1  ) have been investigated using the density functional theory method. The geometries, harmonic frequencies, and energies were calculated at the B3LYP/6-311+G(d,p) level. Two stable structures, cis and trans isomers with respect to carbon-carbon double bond, were found to be local minima of the potential energy surface. The trans isomer of the majority of the studied decalactones is stabilized mainly for hyperconjugative interactions involving the unshared electrons pair of oxigen atoms and pi anti-bonding orbital of carbonyl group as well as sigma anti-bonding orbital of C9-H.

Theoretical study of hyperconjugative interactions effects on the conformational stability of unsaturated decalactones

246th National Meeting (2013)

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