The cyclohexanol dimer and the monohydrate: Internal rotation and conversion from transient to permanent chirality

Juanes, Marcos

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https://hdl.handle.net/2142/100734 Copy

Description

Title

The cyclohexanol dimer and the monohydrate: Internal rotation and conversion from transient to permanent chirality

Author(s)

Juanes, Marcos

Contributor(s)

• Lesarri, Alberto
• Caminati, Walther
• Evangelisti, Luca
• Li, Weixing
• Rubio, José Emiliano
• Pinacho, Ruth
• León, Iker

Issue Date

2018-06-20

Keyword(s)

Structure determination

Abstract

The conformational preferences, molecular structure and intramolecular dynamics of cyclohexanol (CHOL), the cyclohexanol dimer (CHOL2) and cyclohexanol-water (CHOL···H2O) have been analyzed using rotational spectroscopy in a supersonic jet expansion. The monomer conformation is controlled by ring inversion (equatorial/axial) and alcohol internal rotation (gauche+/gauche- or trans). Both equatorial trans (rigid) and equatorial gauche (tunneling) isomers were observed, but axial cyclohexanol went undetected. The monohydrate CHOL···H2O exhibits a single hydrogen bonded equatorial gauche conformation, with tunneling splittings revealing a concerted motion of the hydroxyl and water molecules. The formation of the dimer CHOL2 stabilizes the transient chirality of the gauche+/gauche- monomer conformations, as different chiral combinations donor-acceptor result in permanent chirality. This molecular dimer represent a larger level of complexity compared with previous studies ab, as 36 different donor-acceptor combinations are now possible and the relative orientation of the two rings generates multiple conformations. Finally, six different isomers were observed for the dimer. Accurate rotational parameters for the observed conformations and supporting ab initio and DFT calculations will be reported.

Publisher

International Symposium on Molecular Spectroscopy

Type of Resource

text

Language

eng

Permalink

http://hdl.handle.net/2142/100734

DOI

10.15278/isms.2018.WK09

Copyright and License Information

Copyright 2018 Marcos Juanes

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