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

dc.contributor.authorKrin, Anna
dc.contributor.authorPérez-Cuadrado, Cristóbal
dc.contributor.authorPinacho, Pablo
dc.contributor.authorQuesada-Moreno, María Mar
dc.contributor.authorLópez-González, Juan Jesús
dc.contributor.authorAvilés-Moreno, Juan Ramón
dc.contributor.authorBlanco-Rodríguez, Susana
dc.contributor.authorLópez-Alonso, Juan Carlos
dc.contributor.authorSchnell, Melanie
dc.date.accessioned2025-01-30T10:19:06Z
dc.date.available2025-01-30T10:19:06Z
dc.date.issued2018
dc.description.abstractIn 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.es_ES
dc.description.sponsorshipA. K. acknowledges the financial support of the IMPRS-UFAST and the use of the GWDG computing cluster. C. P. acknowledges grant by the Alexander von Humboldt Stiftung. M. M. Q. M. thanks the Universidad de Jaén for a predoctoral fellowship and the Max Planck Society and the Prince of Asturias Foundation for a Max Planck-Prince of Asturias Award Mobility Grant. The authors are also thankful to the Centro de Servicios de Informática y Redes de Comunicaciones (CSIRC), University of Granada (UGR), for computational time and facilities. J. C. L, S. B., and P. P. acknowledge the Ministerio de Economía y Competitividad (Grant CTQ 2016-75253-P) for financial support. P. P. acknowledges the University of Valladolid for a mobility grant.es_ES
dc.identifier.citationChem. Eur. J. 2018, 24, 721 – 729es_ES
dc.identifier.issn0947-6539es_ES
dc.identifier.other10.1002/chem.201704644es_ES
dc.identifier.urihttps://hdl.handle.net/10953/4572
dc.language.isoenges_ES
dc.publisherWileyes_ES
dc.relation.ispartofChem. Eur. J.es_ES
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectChiralityes_ES
dc.subjectInternal rotationes_ES
dc.subjectMicrowave spectroscopyes_ES
dc.subjectMicrowave three-wave mixinges_ES
dc.subjectTerpeneses_ES
dc.titleStructure Determination, Conformational Flexibility, Internal Dynamics, and Chiral Analysis of Pulegone and Its Complex with Wateres_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.type.versioninfo:eu-repo/semantics/acceptedVersiones_ES

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