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HERO ID
4900928
Reference Type
Journal Article
Title
Cyanocyclohexane: Axial-to-equatorial "seesaw" parity in gas and condensed phases
Author(s)
Tran Dinh Phien; Kuzmina, LE; Kvaran, A; Jonsdottir, S; Arnason, I; Shlykov, SA
Year
2018
Is Peer Reviewed?
Yes
Journal
Journal of Molecular Structure
ISSN:
0022-2860
EISSN:
1872-8014
Volume
1168
Page Numbers
127-134
DOI
10.1016/j.molstruc.2018.05.013
Web of Science Id
WOS:000435622500013
Abstract
Conformational properties and molecular structure of cyanocyclohexane 1 were studied by gas-phase electron diffraction (GED) and dynamic NMR as well as by detailed quantum chemical (QC) computations. This compound violates the so called 'equatorial rule' according to which the substituents attached to one of the carbon atom of the ring prefers to occupy an equatorial position relative to the frame of cyclohexane. In case of 1, both conformers contribute nearly equally in gas and liquid phases, with slight domination of the equatorial form as found from the experimental data, Eq:Ax of ca. 3:2. The QC calculations predict contradictive conformer preference depending on method/basis set combination applied. Enthalpy and entropy contributions to Eq <-> Ax equilibrium are analyzed. (C) 2018 Elsevier B.V. All rights reserved.
Keywords
Cyanocyclohexane; Gas-phase electron diffraction; Dynamic NMR; Quantum chemical calculations; Equatorial-to-axial equilibrium; Molecular structure
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