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4900928 
Journal Article 
Cyanocyclohexane: Axial-to-equatorial "seesaw" parity in gas and condensed phases 
Tran Dinh Phien; Kuzmina, LE; Kvaran, A; Jonsdottir, S; Arnason, I; Shlykov, SA 
2018 
Yes 
Journal of Molecular Structure
ISSN: 0022-2860
EISSN: 1872-8014 
1168 
127-134 
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. 
Cyanocyclohexane; Gas-phase electron diffraction; Dynamic NMR; Quantum chemical calculations; Equatorial-to-axial equilibrium; Molecular structure