RT info:eu-repo/semantics/article
T1 Structure Determination, Conformational Flexibility, Internal Dynamics, and Chiral Analysis of Pulegone and Its Complex with Water
A1 Krin, Anna
A1 Pérez, Cristóbal
A1 Pinacho Morante, Pablo
A1 Quesada Moreno, María Mar
A1 López González, Juan Jesús
A1 Avilés Moreno, Juan Ramón
A1 Blanco Rodríguez, Susana
A1 López Alonso, Juan Carlos
A1 Schnell, Melanie
K1 Quimica
K1 Espectroscopía de rotación
K1 Water cluster
K1 microsolvation
K1 rotational spectroscopy
K1 structure
K1 Pulegone
K1 Chirality
K1 23 Química
K1 2301.13 Espectroscopia de Microondas
K1 2307 Química Física
AB 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 isopropylideneside 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.
PB Wiley-V C H Verlag Gmbh
SN 0947-6539
YR 2018
FD 2018
LK http://uvadoc.uva.es/handle/10324/46232
UL http://uvadoc.uva.es/handle/10324/46232
LA spa
NO Chemistry: A European Journal, 2018, vol. 24, p. 721-729
NO Producción Científica
DS UVaDOC
RD 01-sep-2024