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Article Dans Une Revue Journal of Chemical Physics Année : 2017

The gas phase structure of α-pinene, a main biogenic volatile organic compound

Elias M Neeman
Juan Ramón Avilés Moreno

Résumé

The rotational spectrum of the bicyclic molecule fenchol (C 10 H 18 O, 1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol)-a biogenic volatile organic compound-was recorded in the gas phase using an impulse Fourier transform microwave spectrometer coupled to a supersonic jet expansion over the 2-20 GHz range. Quantum chemical calculations were performed to characterize the conformational landscape of the two diastereoisomers, endo-fenchol and exo-fenchol, with respect to the orientation of the hydroxyl group. The three most stable structures for each diastereoisomer were optimized at the MP2/6-311++G(2df,p) level of theory. Two of them were found to be very close in energy. Molecular parameters obtained from the analysis of observed signals led to the observation of one conformer per diastereoisomer. For the endo-fenchol molecule the r s geometry associated with the hydroxyl group was obtained, from the observation and analysis of the rotational spectra associated with the deuterated hydroxyl group. The nuclear quadrupolar hyperfine signature was identified. The hydroxyl group was found to be oriented into the direction of the methyl groups attached to C 3 , for the more stable conformer of endo-fenchol. For exo-fenchol, it is oriented into the methyl group attached to C 1 .
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Dates et versions

hal-02068297 , version 1 (14-03-2019)

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Elias M Neeman, Juan Ramón Avilés Moreno, Thérèse Huet. The gas phase structure of α-pinene, a main biogenic volatile organic compound. Journal of Chemical Physics, 2017, 147 (21), pp.214305. ⟨10.1063/1.5003726⟩. ⟨hal-02068297⟩
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