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Título
Structure Determination, Conformational Flexibility, Internal Dynamics, and Chiral Analysis of Pulegone and Its Complex with Water
Autor
Año del Documento
2018
Editorial
Wiley-V C H Verlag Gmbh
Descripción
Producción Científica
Documento Fuente
Chemistry: A European Journal, 2018, vol. 24, p. 721-729
Zusammenfassung
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) kJmol-1 and 6.3617(12) kJmol-1 for one conformer, and 1.96094(74) kJmol-1 and 6.705(44) kJmol-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) kJmol-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.
Materias (normalizadas)
Quimica
Espectroscopía de rotación
Materias Unesco
23 Química
2301.13 Espectroscopia de Microondas
2307 Química Física
Palabras Clave
Water cluster
microsolvation
rotational spectroscopy
structure
Pulegone
Chirality
ISSN
0947-6539
Revisión por pares
SI
Patrocinador
Ministerio de economia, industria y competitividad CTQ2016-75253-P
Propietario de los Derechos
Wiley-V C H Verlag Gmbh
Idioma
spa
Tipo de versión
info:eu-repo/semantics/draft
Derechos
openAccess
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