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.; Blanco, S.; López, J. C.; Schnell, M.

doi:10.1002/chem.201704644

アイテム詳細

登録内容を編集ファイル形式で保存

一時保存へ追加

タグ情報を表示リリース履歴を表示詳細要約

公開

学術論文

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

MPS-Authors

/persons/resource/persons146333

Krin, A.
Deutsches Elektronen-Synchrotron;
Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;
Christian-Albrechts-Universität zu Kiel, Institute of Physical Chemistry;

/persons/resource/persons188136

Pérez, C.
Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;

/persons/resource/persons22077

Schnell, M.
Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society;

External Resource

https://dx.doi.org/10.1002/chem.201704644
(出版社版)

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

フルテキスト (公開)

公開されているフルテキストはありません

付随資料 (公開)

ard_sdccm_2018_krin_chem-eur-j_24_3_721_suppl.pdf
(付録資料), 4MB

引用

Krin, A., Pérez, C., Pinacho, P., Quesada‐Moreno, M. M., López‐González, J. J., Avilés‐Moreno, J. R., Blanco, S., López, J. C., & Schnell, M. (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.

引用: https://hdl.handle.net/21.11116/0000-0001-F59B-C

要旨

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.