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The two have equal free energy; neither is more stable, so neither predominates compared to the other. A negative difference in free energy means that a conformer interconverts to a thermodynamically more stable conformation, thus the equilibrium constant will always be greater than 1.
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]
When two fluorine atoms are in vicinal (i.e., adjacent) carbons, as in 1,2-difluoroethane (H 2 FCCFH 2), the gauche conformer is more stable than the anti conformer—this is the opposite of what would normally be expected and to what is observed for most 1,2-disubstituted ethanes; this phenomenon is known as the gauche effect. [9]
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 ...
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.
This may be a dynamic equilibrium in which individual atoms or molecules change form, but their overall number in a particular form is conserved. This type of chemical thermodynamic equilibrium will persist indefinitely unless the system is changed. Chemical systems might undergo changes in the phase of matter or a set of chemical reactions.
The Curtin–Hammett principle is a principle in chemical kinetics proposed by David Yarrow Curtin and Louis Plack Hammett.It states that, for a reaction that has a pair of reactive intermediates or reactants that interconvert rapidly (as is usually the case for conformational isomers), each going irreversibly to a different product, the product ratio will depend both on the difference in ...
The molecular motions involved in a chair flip are detailed in the figure on the right: The half-chair conformation (D, 10.8 kcal/mol, C 2 symmetry) is the energy maximum when proceeding from the chair conformer (A, 0 kcal/mol reference, D 3d symmetry) to the higher energy twist-boat conformer (B, 5.5 kcal/mol, D 2 symmetry).