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A cyclohexane molecule in chair conformation. Hydrogen atoms in axial positions are shown in red, while those in equatorial positions are in blue. Cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and ...
According to the VSEPR theory of molecular geometry, an axial position is more crowded because an axial atom has three neighboring equatorial atoms (on the same central atom) at a 90° bond angle, whereas an equatorial atom has only two neighboring axial atoms at a 90° bond angle. For molecules with five identical ligands, the axial bond ...
Substituents on a cyclohexane ring prefer to reside in the equatorial position to the axial. The difference in Gibbs free energy (ΔG) between the higher energy conformation (axial substitution) and the lower energy conformation (equatorial substitution) is the A-value for that particular substituent.
Axial and equatorial positions are not distinguished; instead, substituents are positioned directly above or below the ring atom to which they are connected. Hydrogen substituents are typically omitted. However, an important thing to keep in mind while reading an Haworth projection is that the ring structures are not flat.
The ideal angle between the axial ligands and the equatorial ligands is 90°; whereas the ideal angle between the two equatorial ligands themselves is 120°. Disphenoidal molecules, like trigonal bipyramidal ones, are subject to Berry pseudorotation in which the axial ligands move to equatorial positions and vice versa. This exchange of ...
In the case of cyclic systems, the steric effect and contribution to the free energy can be approximated by A values, which measure the energy difference when a substituent on cyclohexane in the axial as compared to the equatorial position. In large (>14 atom) rings, there are many accessible low-energy conformations which correspond to the ...
Trigonal bipyramid molecules have both with axial and equatorial positions. If there are two types of substituents, the more electronegative substituent will prefer the axial position as there are smaller bond angles between axial and electronegative substituents than between two equatorial substituents. [23]
The α- and β-anomers of D-glucopyranose.. In organic chemistry, the anomeric effect or Edward-Lemieux effect (after J. T. Edward and Raymond Lemieux) is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of the less-hindered equatorial orientation that would be expected ...