Krin, AnnaPérez-Cuadrado, CristóbalPinacho, PabloQuesada-Moreno, María MarLópez-González, Juan JesúsAvilés-Moreno, Juan RamónBlanco-Rodríguez, SusanaLópez-Alonso, Juan CarlosSchnell, Melanie2025-01-302025-01-302018Chem. Eur. J. 2018, 24, 721 – 7290947-653910.1002/chem.201704644https://hdl.handle.net/10953/4572In 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 and 6.3617(12) kJ/mol for one conformer, and 1.96094(74) kJ/mol and 6.705(44) kJ/mol 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 via 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. 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.engAtribución-NoComercial-SinDerivadas 3.0 Españahttp://creativecommons.org/licenses/by-nc-nd/3.0/es/ChiralityInternal rotationMicrowave spectroscopyMicrowave three-wave mixingTerpenesinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccess