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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 determination of stable conformations has also played a large role in the establishment of the concept of asymmetric induction and the ability to predict ...
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 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 ...
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.
As the bond angle is distorted, the energy for each of the orbitals can be followed along the lines, allowing a quick approximation of molecular energy as a function of conformation. It is still unclear whether or not the Walsh ordinate considers nuclear repulsion, and this remains a topic of debate. [21]
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 ...
On this continuum the energy varies because of Pitzer strain related to the dihedral angles. The twist boat has a lower energy than the boat. In order to go from the chair conformation to a twist-boat conformation or the other chair conformation, bond angles have to be changed, leading to a high-energy half-chair conformation.
As shown by the relative structure energies in the diagram above, the chair structures are the most stable carbohydrate form. This relatively defined and stable conformation means that the hydrogen atoms of the pyranose ring are held at relatively constant angles to one another.