Structure Determination, Conformational Flexibility, Internal Dynamics, and 
Chiral Analysis of Pulegone and Its Complex with Water

Krin, A.; Pérez, C.; Pinacho, P.; Quesada‐Moreno, M. M.; López‐González, J. J.; Avilés‐Moreno, J. R.; Blanco, S.; López, J. C.; Schnell, M.

doi:10.1002/chem.201704644

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Structure Determination, Conformational Flexibility, Internal Dynamics, and Chiral Analysis of Pulegone and Its Complex with Water

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Krin, A.
Deutsches Elektronen-Synchrotron;
Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;
Christian-Albrechts-Universität zu Kiel, Institute of Physical Chemistry;

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Pérez, C.
Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;

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Schnell, M.
Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;

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https://dx.doi.org/10.1002/chem.201704644
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Citation

Krin, A., Pérez, C., Pinacho, P., Quesada‐Moreno, M. M., López‐González, J. J., Avilés‐Moreno, J. R., et al. (2018). Structure Determination, Conformational Flexibility, Internal Dynamics, and Chiral Analysis of Pulegone and Its Complex with Water. Chemistry – A European Journal, 24(3), 721-729. doi:10.1002/chem.201704644.

Cite as: https://hdl.handle.net/21.11116/0000-0001-F59B-C

Abstract

In the current work we present a detailed analysis of the chiral molecule pulegone, which is a constituent of essential oils, using broadband rotational spectroscopy. Two conformers are observed under the cold conditions of a molecular jet. We report an accurate experimentally determined structure for the lowest energy conformer. For both conformers, a characteristic splitting pattern is observed in the spectrum, resulting from the internal rotation of the two non‐equivalent methyl groups situated in the isopropylidene side chain. The determined energy barriers are 1.961911(46) kJ mol−1 and 6.3617(12) kJ mol−1 for one conformer, and 1.96094(74) kJ mol−1 and 6.705(44) kJ mol−1 for the other one. Moreover, a cluster of the lowest energy conformer with one water molecule is reported. The water molecule locks one of the methyl groups by means of a hydrogen bond and some secondary interactions, so that we only observe internal rotation splittings from the other methyl group with an internal rotation barrier of 2.01013(38) kJ mol−1. Additionally, the chirality‐sensitive microwave three‐wave mixing technique is applied for the differentiation between the enantiomers, which can become of further use for the analysis of essential oils.