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The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]
The staggered conformation is more stable by 12.5 kJ/mol than the eclipsed conformation, which is the energy maximum for ethane. In the eclipsed conformation the torsional angle is minimised. staggered conformation left, eclipsed conformation right in Newman projection
The chair conformation is the most stable conformer. At 298 K (25 °C), 99.99% of all molecules in a cyclohexane solution adopt this conformation. The C–C ring of the chair conformation has the same shape as the 6-membered rings in the diamond cubic lattice. [7]: 16 This can be modeled as follows.
More complex molecules, such as butane, have more than one possible staggered conformation. The anti conformation of butane is approximately 0.9 kcal mol −1 (3.8 kJ mol −1) more stable than the gauche conformation. [1] Both of these staggered conformations are much more stable than the eclipsed conformations.
Graphane is effectively made up of cyclohexane units, and, in parallel to cyclohexane, the most stable structural conformation is not planar, but an out-of-plane structure, including the chair and boat conformers, in order to minimize ring strain and allow for the ideal tetrahedral bond angle of 109.5° for sp 3-bonded atoms. However, in ...
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Rather than the strain that would normally occur in the close group proximity, the hydrogen bond stabilizes the conformation and makes it energetically much more favorable. This scenario occurs when the allylic substituent at the 1 position is a hydrogen bond donor (usually a hydroxyl ) and the substituent at the 3 position is a hydrogen bond ...
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