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  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., 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.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0001-F59B-C Version Permalink: http://hdl.handle.net/21.11116/0000-0001-F59C-B
Genre: Journal Article

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Krin_et_al-2018-Chemistry_-_A_European_Journal.pdf (Publisher version), 2MB
 
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https://dx.doi.org/10.1002/chem.201704644 (Publisher version)
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 Creators:
Krin, A.1, 2, 3, Author              
Pérez, C.2, Author              
Pinacho, P.4, Author
Quesada‐Moreno, M. M.5, Author
López‐González, J. J.5, Author
Avilés‐Moreno, J. R.4, Author
Blanco, S.6, Author
López, J. C.6, Author
Schnell, M.2, Author              
Affiliations:
1Deutsches Elektronen-Synchrotron, ou_persistent22              
2Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society, ou_1938292              
3Christian-Albrechts-Universität zu Kiel, Institute of Physical Chemistry, ou_persistent22              
4Departamento de Sistemas Físicos, Químicos y Naturales, Universidad Pablo de Olavide Sevilla, ou_persistent22              
5Departamento de Química Física y Analítica, Universidad de Jaén, ou_persistent22              
6Departamento de Química Física y Química Inorgánica, Universidad de Valladolid, ou_persistent22              

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Free keywords: chirality, internal rotation, microwave, spectroscopy, microwave three-wavemixing, terpenes
 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.

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Language(s): eng - English
 Dates: 2017-09-302017-12-062018-01-12
 Publication Status: Published in print
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201704644
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 24 (3) Sequence Number: - Start / End Page: 721 - 729 Identifier: ISSN: 0947-6539
CoNE: /journals/resource/954926979058