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The existence of specific conformations is due to hindered rotation around sigma bonds, although a role for hyperconjugation is proposed by a competing theory. The importance of energy minima and energy maxima is seen by extension of these concepts to more complex molecules for which stable conformations may be predicted as minimum-energy forms.
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.
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]
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.
Hyperconjugation can be used to rationalize a variety of chemical phenomena, including the anomeric effect, the gauche effect, the rotational barrier of ethane, the beta-silicon effect, the vibrational frequency of exocyclic carbonyl groups, and the relative stability of substituted carbocations and substituted carbon centred radicals, and the thermodynamic Zaitsev's rule for alkene stability.
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 ...
The structure was found, using a cluster expansion method, to be the most stable of all the possible hydrogenation ratios of graphene. [4] In 2007, researchers found that the compound is more stable than other compounds containing carbon and hydrogen, such as benzene, cyclohexane and polyethylene. [1]
Six electron AH 3 molecules should have a planar conformation. It can be seen that the HOMO, 1e’, of planar AH 3 is destabilized upon bending of the A-H bonds to form a pyramid shape, due to disruption of bonding. The LUMO, which is concentrated on one atomic center, is a good electron acceptor and explains the Lewis acid character of BH 3 ...